Dyes and Pigments最新文献_第6页

Laser-induced fluorescence spectroscopic investigation of Echium amoenum decoction 对 Echium amoenum 煎剂的激光诱导荧光光谱研究

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-10-09 DOI: 10.1016/j.dyepig.2024.112481

Ali Rahmatpanahi, Ali Bavali

Herbs containing medicinal ingredients with nutritional value have recently gained attention as an alternative to synthetic drugs. Aside from their pharmaceutical worthiness, a variety of naturally occurring chromophores with specific optical properties have made them valuable sources of natural pigments for many biophotonic applications. Echium Amoenum (EA) is one of the colorful flowers that has been used in traditional medicine for a long time. To our knowledge, although several studies have been carried out on the characterization of EA ingredients and their chemical activities, information on EA fluorescence is still lacking. Here, laser induced fluorescence (LIF) features of the decoction of EA petals were evaluated and found to be highly dependent on the excitation wavelength, EA concentration, and detection geometry. The abundance of pigments, the boundaries of their absorption/emission spectral regions, and the corresponding energy transfer ascertain the contribution of certain chromophores to the cumulative fluorescence activity. Upon deconvolution of the LIF spectra, it was revealed that the different emission bands of rosmarinic acid (corresponding to its dissociated forms) and the luminescent activity of luteolin and β-carotene mainly determine the quantum distribution of the fluorescence of EA. Angular measurement of LIF in a symmetric cylindrical arrangement revealed the presence of the inner filters mainly due to the reabsorption of LIF photons by anthocyanins (flavone, pelargonidin, delphinidin and cyanidin) and carotenoids. We hope that the obtained results will be useful in various fields of photochemistry and biophotonics.

作为合成药物的替代品，含有营养价值药用成分的草药近来备受关注。除了具有药用价值外，多种具有特殊光学特性的天然发色团也使它们成为许多生物光子应用的宝贵天然色素来源。Echium Amoenum（EA）是彩色花卉之一，长期以来一直被用于传统医药。据我们所知，虽然已经开展了多项关于 EA 成分特征及其化学活性的研究，但有关 EA 荧光的信息仍然缺乏。本文评估了 EA 花瓣煎剂的激光诱导荧光（LIF）特征，发现其与激发波长、EA 浓度和检测几何形状有很大关系。色素的丰度、其吸收/发射光谱区的边界以及相应的能量转移确定了某些发色团对累积荧光活性的贡献。对 LIF 光谱进行解卷积后发现，迷迭香酸（对应于其解离形式）的不同发射带以及木犀草素和β-胡萝卜素的发光活性主要决定了 EA 荧光的量子分布。在对称圆柱形排列中对 LIF 进行角度测量发现，内部滤光器的存在主要是由于花青素（黄酮、鹅掌楸黄素、鹅掌楸黄素和青黄素）和类胡萝卜素对 LIF 光子的再吸收。我们希望这些研究成果能在光化学和生物光子学的各个领域发挥作用。

{"title":"Laser-induced fluorescence spectroscopic investigation of Echium amoenum decoction","authors":"Ali Rahmatpanahi, Ali Bavali","doi":"10.1016/j.dyepig.2024.112481","DOIUrl":"10.1016/j.dyepig.2024.112481","url":null,"abstract":"<div><div>Herbs containing medicinal ingredients with nutritional value have recently gained attention as an alternative to synthetic drugs. Aside from their pharmaceutical worthiness, a variety of naturally occurring chromophores with specific optical properties have made them valuable sources of natural pigments for many biophotonic applications. Echium Amoenum (EA) is one of the colorful flowers that has been used in traditional medicine for a long time. To our knowledge, although several studies have been carried out on the characterization of EA ingredients and their chemical activities, information on EA fluorescence is still lacking. Here, laser induced fluorescence (LIF) features of the decoction of EA petals were evaluated and found to be highly dependent on the excitation wavelength, EA concentration, and detection geometry. The abundance of pigments, the boundaries of their absorption/emission spectral regions, and the corresponding energy transfer ascertain the contribution of certain chromophores to the cumulative fluorescence activity. Upon deconvolution of the LIF spectra, it was revealed that the different emission bands of rosmarinic acid (corresponding to its dissociated forms) and the luminescent activity of luteolin and β-carotene mainly determine the quantum distribution of the fluorescence of EA. Angular measurement of LIF in a symmetric cylindrical arrangement revealed the presence of the inner filters mainly due to the reabsorption of LIF photons by anthocyanins (flavone, pelargonidin, delphinidin and cyanidin) and carotenoids. We hope that the obtained results will be useful in various fields of photochemistry and biophotonics.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112481"},"PeriodicalIF":4.1,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434005","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Exploring the Thermochromic Properties of Fluoran-Based Complexes: Synthesis, Structural Influence, and Application in Temperature Sensing 探索基于氟的配合物的热变色特性：合成、结构影响及在温度传感中的应用

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-10-09 DOI: 10.1016/j.dyepig.2024.112483

Wei Luo , Yanhua Qin , Zhen Ma , Liang Wang , Qiao Cheng , Chao Tan , Meijun Zhang , Hankun Zhang , Benhua Wang , Xiangzhi Song

Fluoran dyes are extensively used as key components of thermochromic materials. To expand the scope of fluoran-based thermochromic systems, we conducted a comprehensive study to explore the relationships between the thermochromic properties of three-component complexes and the types and ratios of their constituents: fluoran dyes, developers, and solvents. We synthesized twenty-one fluoran dyes with varied chemical structures, including differences in the carbon chain length of the dialkylamino group, substitutions with electron-donating and electron-withdrawing groups, and the enlargement of conjugation systems. By combining these dyes with several phenolic developers and three long-chain alcohols, we prepared numerous thermochromic complexes and evaluated their color-changing behaviors under temperature variations. Complexes utilizing developers, bisphenol (BPA), bisphenol S (BPS), 4-hydroxy-4'-isopropoxydiphenylsulfone (D-8), 2,4'-dihydroxydiphenyl sulfone (2, 4'-BPS), and octyl gallate (OG) exhibited a red-to-colorless transition with increasing temperature, whereas those with developer lauryl gallate (LG) displayed a colorless-to-red transition upon heating. The chain length and conjugation extension of fluoran dyes influenced the optimal ratio of the three components. Additionally, substituents on the xanthene moiety of fluoran dyes didn’t impact their complex performance. Finally, we demonstrated the fabrication of these thermochromic complexes on filter papers, showcasing their sensitivity to temperature fluctuations and highlighting their potential application as temperature sensors.

氟素染料被广泛用作热致变色材料的关键成分。为了扩大以芴为基础的热致变色系统的范围，我们进行了一项综合研究，探索三组分复合物的热致变色特性与其组成成分（芴染料、显影剂和溶剂）的类型和比例之间的关系。我们合成了 21 种化学结构各异的芴染料，包括二烷基氨基基团碳链长度的不同、供电子基团和吸电子基团的替换以及共轭体系的扩大。通过将这些染料与几种酚类显影剂和三种长链醇结合，我们制备出了许多热致变色络合物，并评估了它们在温度变化下的变色行为。使用双酚（BPA）、双酚 S（BPS）、4-羟基-4'-异丙氧基二苯砜（D-8）、2,4'-二羟基二苯砜（2,4'-BPS）和没食子酸辛酯（OG）等显色剂的复合物在温度升高时表现出红色到无色的转变，而使用没食子酸月桂酯（LG）等显色剂的复合物在加热时表现出无色到红色的转变。芴染料的链长和共轭延伸影响了三种成分的最佳比例。此外，芴染料的呫吨分子上的取代基并不影响其复合物性能。最后，我们演示了在滤纸上制作这些热致变色复合物的过程，展示了它们对温度波动的敏感性，并突出了它们作为温度传感器的潜在应用。

{"title":"Exploring the Thermochromic Properties of Fluoran-Based Complexes: Synthesis, Structural Influence, and Application in Temperature Sensing","authors":"Wei Luo , Yanhua Qin , Zhen Ma , Liang Wang , Qiao Cheng , Chao Tan , Meijun Zhang , Hankun Zhang , Benhua Wang , Xiangzhi Song","doi":"10.1016/j.dyepig.2024.112483","DOIUrl":"10.1016/j.dyepig.2024.112483","url":null,"abstract":"<div><div>Fluoran dyes are extensively used as key components of thermochromic materials. To expand the scope of fluoran-based thermochromic systems, we conducted a comprehensive study to explore the relationships between the thermochromic properties of three-component complexes and the types and ratios of their constituents: fluoran dyes, developers, and solvents. We synthesized twenty-one fluoran dyes with varied chemical structures, including differences in the carbon chain length of the dialkylamino group, substitutions with electron-donating and electron-withdrawing groups, and the enlargement of conjugation systems. By combining these dyes with several phenolic developers and three long-chain alcohols, we prepared numerous thermochromic complexes and evaluated their color-changing behaviors under temperature variations. Complexes utilizing developers, bisphenol (<strong>BPA</strong>), bisphenol S (<strong>BPS</strong>), 4-hydroxy-4'-isopropoxydiphenylsulfone (<strong>D-8</strong>), 2,4'-dihydroxydiphenyl sulfone (<strong>2, 4'-BPS</strong>), and octyl gallate (<strong>OG</strong>) exhibited a red-to-colorless transition with increasing temperature, whereas those with developer lauryl gallate (<strong>LG</strong>) displayed a colorless-to-red transition upon heating. The chain length and conjugation extension of fluoran dyes influenced the optimal ratio of the three components. Additionally, substituents on the xanthene moiety of fluoran dyes didn’t impact their complex performance. Finally, we demonstrated the fabrication of these thermochromic complexes on filter papers, showcasing their sensitivity to temperature fluctuations and highlighting their potential application as temperature sensors.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112483"},"PeriodicalIF":4.1,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420084","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Near-infrared probes based on the phenanthridinium for dynamic monitoring of viscosity fluctuations during mitophagy 基于菲啶的近红外探针用于动态监测有丝分裂过程中的粘度波动

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-10-06 DOI: 10.1016/j.dyepig.2024.112479

Hong-Xia Wang , Jing-Yu Zhao , Hui Wang , Huan Ma , Jian-Feng Ge , Ru Sun

Abnormal changes in the mitochondrial microenvironment can cause a variety of diseases. Consequently, based on the twisted intramolecular charge transfer (TICT) theory, three hemicyanine fluorescent probes 1a-c were designed and developed by linking the phenanthridine group with different electron donor groups for the dynamic detection of mitochondrial viscosity in this paper. They have the advantages of near-infrared emission, excellent pH stability and viscosity sensitivity. Optical experiments showed that the maximum absorption and emission wavelengths of the probes in different solvents located at 411 − 529 nm and 623 − 684 nm with large Stokes shifts of 133 – 230 nm. In addition, when the viscosity increased from 0.89 cP to 856 cP, their fluorescence intensities in glycerol enhanced by 115-fold, 83-fold and 303-fold compared with water, respectively. The fluorescence intensities of probes showed excellent fit to the Forster Hoffmann equation, and exhibited nearly OFF-ON response to viscosity. Moreover, the probe 1a with good photostability and low cytotoxicity could target mitochondria. It was verified that 1a also could detect variation in mitochondrial viscosity during autophagy by modelling starvation and drug-induced (rapamycin and nystatin) in HeLa cells. Therefore, this study provides a useful probe for the analysis of mitophagy process in HeLa cells by the viscosity variation of mitochondria.

线粒体微环境的异常变化可导致多种疾病。因此，本文基于扭曲分子内电荷转移（TICT）理论，通过将菲啶基团与不同的电子供体基团连接，设计并开发了三种半氰基荧光探针 1a-c，用于线粒体粘度的动态检测。它们具有近红外发射、优异的 pH 稳定性和粘度敏感性等优点。光学实验表明，探针在不同溶剂中的最大吸收和发射波长分别位于 411 - 529 nm 和 623 - 684 nm，并有 133 - 230 nm 的较大斯托克斯位移。此外，当粘度从 0.89 cP 增加到 856 cP 时，探针在甘油中的荧光强度比在水中分别增强了 115 倍、83 倍和 303 倍。探针的荧光强度与福斯特-霍夫曼方程有很好的拟合，对粘度的反应几乎是 "OFF-ON"。此外，探针 1a 具有良好的光稳定性和较低的细胞毒性，可以靶向线粒体。通过模拟饥饿和药物诱导（雷帕霉素和硝司他丁），在 HeLa 细胞中验证了 1a 也能检测自噬过程中线粒体粘度的变化。因此，这项研究为通过线粒体的粘度变化分析 HeLa 细胞的有丝分裂过程提供了一个有用的探针。

{"title":"Near-infrared probes based on the phenanthridinium for dynamic monitoring of viscosity fluctuations during mitophagy","authors":"Hong-Xia Wang , Jing-Yu Zhao , Hui Wang , Huan Ma , Jian-Feng Ge , Ru Sun","doi":"10.1016/j.dyepig.2024.112479","DOIUrl":"10.1016/j.dyepig.2024.112479","url":null,"abstract":"<div><div>Abnormal changes in the mitochondrial microenvironment can cause a variety of diseases. Consequently, based on the twisted intramolecular charge transfer (TICT) theory, three hemicyanine fluorescent probes <strong>1a-c</strong> were designed and developed by linking the phenanthridine group with different electron donor groups for the dynamic detection of mitochondrial viscosity in this paper. They have the advantages of near-infrared emission, excellent pH stability and viscosity sensitivity. Optical experiments showed that the maximum absorption and emission wavelengths of the probes in different solvents located at 411 − 529 nm and 623 − 684 nm with large Stokes shifts of 133 – 230 nm. In addition, when the viscosity increased from 0.89 cP to 856 cP, their fluorescence intensities in glycerol enhanced by 115-fold, 83-fold and 303-fold compared with water, respectively. The fluorescence intensities of probes showed excellent fit to the Forster Hoffmann equation, and exhibited nearly OFF-ON response to viscosity. Moreover, the probe <strong>1a</strong> with good photostability and low cytotoxicity could target mitochondria. It was verified that <strong>1a</strong> also could detect variation in mitochondrial viscosity during autophagy by modelling starvation and drug-induced (rapamycin and nystatin) in HeLa cells. Therefore, this study provides a useful probe for the analysis of mitophagy process in HeLa cells by the viscosity variation of mitochondria.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112479"},"PeriodicalIF":4.1,"publicationDate":"2024-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420085","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Two strategies of enhancing the therapeutic potential of a coumarin probe: Integration of a protonatable moiety and BSA-based nanoparticle formation 增强香豆素探针治疗潜力的两种策略：可质子化分子的整合与基于 BSA 的纳米粒子的形成

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-10-03 DOI: 10.1016/j.dyepig.2024.112475

Gahyun Kim , Jeonghye Han , Van Kieu Thuy Nguyen , Seongman Lee , Suhong Min , Subin Park , Thanh Chung Pham , Songyi Lee

Photodynamic therapy (PDT) represents a promising non-invasive approach for cancer treatment, relying on photosensitizers (PSs) to generate reactive oxygen species (ROS) upon light activation. This study aims to enhance the therapeutic potential of a coumarin-based fluorescent probe by employing two strategic modifications: the integration of a protonatable lysosome-targeting moiety and the formation of bovine serum albumin (BSA)-based nanoparticles. The COM molecule was synthesized with a morpholine moiety to facilitate lysosome targeting and protonation in acidic environments, thereby enhancing ROS production and promoting lysosomal dysfunction for increased cancer cell apoptosis. Additionally, COM was encapsulated in BSA nanoparticles (COM-BSA NPs) to leverage hydrophobic interactions and hydrogen bonding, which enhance ROS generation by promoting the intersystem crossing (ISC) process. Comprehensive photophysical studies confirmed the enhanced ROS generation under acidic conditions and within BSA-based NPs. Cellular experiments demonstrated effective lysosome targeting and anticancer efficacy of both COM and COM-BSA NPs. These findings highlight the dual benefits of maintaining the bioimaging capabilities of coumarin while significantly improving its therapeutic efficacy in PDT applications.

光动力疗法（PDT）是一种很有前景的非侵入性癌症治疗方法，它依靠光敏剂（PSs）在光激活时产生活性氧（ROS）。本研究旨在通过两种策略性改良来提高香豆素类荧光探针的治疗潜力：一是整合质子可溶酶体靶向分子，二是形成基于牛血清白蛋白（BSA）的纳米颗粒。COM 分子中合成了吗啉基团，以促进溶酶体靶向和在酸性环境中质子化，从而增强 ROS 生成并促进溶酶体功能障碍，增加癌细胞凋亡。此外，COM 还被封装在 BSA 纳米颗粒（COM-BSA NPs）中，以利用疏水相互作用和氢键，通过促进系统间交叉（ISC）过程来增强 ROS 的产生。全面的光物理研究证实，在酸性条件下和基于 BSA 的 NPs 内，ROS 的生成得到了增强。细胞实验证明，COM 和 COM-BSA NPs 都能有效地靶向溶酶体，并具有抗癌功效。这些发现凸显了保持香豆素生物成像能力的双重优势，同时显著提高了其在光透射疗法应用中的疗效。

{"title":"Two strategies of enhancing the therapeutic potential of a coumarin probe: Integration of a protonatable moiety and BSA-based nanoparticle formation","authors":"Gahyun Kim , Jeonghye Han , Van Kieu Thuy Nguyen , Seongman Lee , Suhong Min , Subin Park , Thanh Chung Pham , Songyi Lee","doi":"10.1016/j.dyepig.2024.112475","DOIUrl":"10.1016/j.dyepig.2024.112475","url":null,"abstract":"<div><div>Photodynamic therapy (PDT) represents a promising non-invasive approach for cancer treatment, relying on photosensitizers (PSs) to generate reactive oxygen species (ROS) upon light activation. This study aims to enhance the therapeutic potential of a coumarin-based fluorescent probe by employing two strategic modifications: the integration of a protonatable lysosome-targeting moiety and the formation of bovine serum albumin (BSA)-based nanoparticles. The <strong>COM</strong> molecule was synthesized with a morpholine moiety to facilitate lysosome targeting and protonation in acidic environments, thereby enhancing ROS production and promoting lysosomal dysfunction for increased cancer cell apoptosis. Additionally, <strong>COM</strong> was encapsulated in BSA nanoparticles (<strong>COM-BSA NPs</strong>) to leverage hydrophobic interactions and hydrogen bonding, which enhance ROS generation by promoting the intersystem crossing (ISC) process. Comprehensive photophysical studies confirmed the enhanced ROS generation under acidic conditions and within BSA-based NPs. Cellular experiments demonstrated effective lysosome targeting and anticancer efficacy of both <strong>COM</strong> and <strong>COM-BSA NPs</strong>. These findings highlight the dual benefits of maintaining the bioimaging capabilities of coumarin while significantly improving its therapeutic efficacy in PDT applications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112475"},"PeriodicalIF":4.1,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420097","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Two new thermally activated delayed fluorescent molecules incorporating spiro-acridine donors for sky-blue organic light emitting diode devices demonstrating an impressive 31% EQE 结合螺吖啶供体的两种新型热激活延迟荧光分子，用于天蓝色有机发光二极管器件，显示出令人印象深刻的 31% EQE

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-10-02 DOI: 10.1016/j.dyepig.2024.112478

Aziz Khan , Wang Qiang , Sarvendra Kumar , Tim Leydecker , Zhiming Wang

Organic light-emitting diodes (OLEDs) utilizing thermally activated delayed fluorescence (TADF) materials as the emitting layer are promising candidates for highly efficient light emission. However, they have traditionally faced challenges with achieving high luminance and high external quantum efficiencies (EQEs) in blue region. Here, we report on the design strategy of a donor-acceptor (D-A) type skeleton for highly efficient emitters, SpiroAC-MeTRZ and AdAC-MeTRZ, which incorporate SpiroAC and AdAC as donors and triazine as an acceptor, respectively. The introduction of methyl group on phenyl arms of the acceptor triazine is responsible for shallowing the lowest unoccupied molecular orbital (LUMO). SpiroAC-MeTRZ and AdAC-MeTRZ exhibit higher HOMO and LUMO values (and therefore a larger energy gap, Eg) compared to SpiroAC-TRZ and a-DMAC-TRZ. The photophysical properties of the materials were explored, revealing excellent TADF properties. Moreover, in the case of AdAC-MeTRZ, the emission spectrum exhibits dual fluorescence emission (DFE), which can be ascribed to quasi-axial conformation (QAC) and quasi-equatorial conformation (QEC). The OLED devices fabricated with these materials exhibited efficient performance, with maximum external quantum efficiency (EQE) of 31.4 % and 14.6 % at 484 nm and 472 nm for SpiroAC-MeTRZ and AdAC-MeTRZ, respectively.

利用热激活延迟荧光（TADF）材料作为发光层的有机发光二极管（OLED）有望实现高效发光。然而，它们历来面临着在蓝色区域实现高亮度和高外部量子效率（EQE）的挑战。在此，我们报告了高效发光体--螺AC-MeTRZ 和 AdAC-MeTRZ 的供体-受体（D-A）型骨架的设计策略。在受体三嗪的苯基臂上引入甲基是使最低未占分子轨道（LUMO）变浅的原因。与螺AC-TRZ和a-DMAC-TRZ相比，螺AC-MeTRZ和AdAC-MeTRZ表现出更高的HOMO和LUMO值（因此能隙Eg更大）。我们对这些材料的光物理特性进行了研究，发现它们具有出色的 TADF 特性。此外，AdAC-MeTRZ 的发射光谱表现出双重荧光发射（DFE），这可归因于准轴向构象（QAC）和准赤道构象（QEC）。使用这些材料制造的有机发光二极管器件表现出高效的性能，在 484 纳米波长和 472 纳米波长处，SpiroAC-MeTRZ 和 AdAC-MeTRZ 的最大外部量子效率（EQE）分别为 31.4% 和 14.6%。

{"title":"Two new thermally activated delayed fluorescent molecules incorporating spiro-acridine donors for sky-blue organic light emitting diode devices demonstrating an impressive 31% EQE","authors":"Aziz Khan , Wang Qiang , Sarvendra Kumar , Tim Leydecker , Zhiming Wang","doi":"10.1016/j.dyepig.2024.112478","DOIUrl":"10.1016/j.dyepig.2024.112478","url":null,"abstract":"<div><div>Organic light-emitting diodes (OLEDs) utilizing thermally activated delayed fluorescence (TADF) materials as the emitting layer are promising candidates for highly efficient light emission. However, they have traditionally faced challenges with achieving high luminance and high external quantum efficiencies (EQEs) in blue region. Here, we report on the design strategy of a donor-acceptor (D-A) type skeleton for highly efficient emitters, <strong>SpiroAC-MeTRZ</strong> and <strong>AdAC-MeTRZ</strong>, which incorporate <strong>SpiroAC</strong> and <strong>AdAC</strong> as donors and triazine as an acceptor, respectively. The introduction of methyl group on phenyl arms of the acceptor triazine is responsible for shallowing the lowest unoccupied molecular orbital (LUMO). <strong>SpiroAC-MeTRZ</strong> and <strong>AdAC-MeTRZ</strong> exhibit higher HOMO and LUMO values (and therefore a larger energy gap, <em>E</em>g) compared to SpiroAC-TRZ and a-DMAC-TRZ. The photophysical properties of the materials were explored, revealing excellent TADF properties. Moreover, in the case of <strong>AdAC-MeTRZ</strong>, the emission spectrum exhibits dual fluorescence emission (DFE), which can be ascribed to quasi-axial conformation (QAC) and quasi-equatorial conformation (QEC). The OLED devices fabricated with these materials exhibited efficient performance, with maximum external quantum efficiency (EQE) of 31.4 % and 14.6 % at 484 nm and 472 nm for <strong>SpiroAC-MeTRZ</strong> and <strong>AdAC-MeTRZ</strong>, respectively.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112478"},"PeriodicalIF":4.1,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420093","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Overcoming surface quenching in persistent luminescence nanoparticles with organic ligand coordination: Implications for enhanced optical imaging 利用有机配体配位克服持续发光纳米粒子的表面淬火：对增强光学成像的影响

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-10-02 DOI: 10.1016/j.dyepig.2024.112477

Zhiheng Li , Yarui Wang , Tianshuai Wang , Bing Qi , Jie Wang , Lin Shi , Hong-Bo Cheng

Persistent luminescence nanoparticles (PLNPs) have been considered as excellent luminescent tools for sensitive optical imaging. However, the persistent luminescence (PL) properties of PLNPs are usually suppressed due to severe surface quenching caused by nanoscale size. Despite considerable efforts, the understanding of surface quenching mechanisms remains a challenge. Here we report a surface ligand coordination method to enhance the PL properties of ZnGa₂O₄:Al,Cr (ZGO:AC) PLNPs. ZGO:AC PLNPs coated with organic ligands containing carboxyl groups show enhanced PL intensity and prolonged decay time. Among the six ligands, the phthalic acid (PA) ligands yielded the largest luminescence enhancement effect, on which the PL intensity and decay time increased 3 and 2 times compared with ligand-free ZGO:AC PLNPs, respectively. Density functional theory (DFT) calculations and detailed characterizations demonstrated that surface quenching is suppressed due to the coordination of non-saturated Ga ions and -COO^- of ligands. Finally, ZGO:AC@PA PLNPs were applied in autofluorescence-free bioimaging and exhibited high imaging sensitivity and contrast ratio. These findings provide insights into the surface quenching mechanisms of PLNPs and offer a platform for developing highly emissive PLNPs on nanoscale.

持久发光纳米粒子（PLNPs）一直被认为是灵敏光学成像的绝佳发光工具。然而，由于纳米尺寸造成的严重表面淬火，PLNPs 的持续发光（PL）特性通常会受到抑制。尽管做了大量努力，但对表面淬火机制的理解仍然是一个挑战。在此，我们报告了一种表面配体配位方法来增强 ZnGa2O4:Al,Cr （ZGO:AC）PLNPs 的光致发光特性。镀有含羧基的有机配体的 ZGO:AC PLNPs 显示出更强的聚光强度和更长的衰减时间。在六种配体中，邻苯二甲酸（PA）配体的发光增强效果最好，与不含配体的 ZGO:AC PLNPs 相比，其发光强度和衰减时间分别增加了 3 倍和 2 倍。密度泛函理论（DFT）计算和详细表征表明，由于非饱和镓离子和配体的-COO-配位，表面淬灭被抑制。最后，ZGO:AC@PA PLNPs 被应用于无自荧光生物成像，并表现出很高的成像灵敏度和对比度。这些发现深入揭示了 PLNPs 的表面淬火机制，并为开发纳米级高发射性 PLNPs 提供了一个平台。

{"title":"Overcoming surface quenching in persistent luminescence nanoparticles with organic ligand coordination: Implications for enhanced optical imaging","authors":"Zhiheng Li , Yarui Wang , Tianshuai Wang , Bing Qi , Jie Wang , Lin Shi , Hong-Bo Cheng","doi":"10.1016/j.dyepig.2024.112477","DOIUrl":"10.1016/j.dyepig.2024.112477","url":null,"abstract":"<div><div>Persistent luminescence nanoparticles (PLNPs) have been considered as excellent luminescent tools for sensitive optical imaging. However, the persistent luminescence (PL) properties of PLNPs are usually suppressed due to severe surface quenching caused by nanoscale size. Despite considerable efforts, the understanding of surface quenching mechanisms remains a challenge. Here we report a surface ligand coordination method to enhance the PL properties of ZnGa<sub>2</sub>O<sub>4</sub>:Al,Cr (ZGO:AC) PLNPs. ZGO:AC PLNPs coated with organic ligands containing carboxyl groups show enhanced PL intensity and prolonged decay time. Among the six ligands, the phthalic acid (PA) ligands yielded the largest luminescence enhancement effect, on which the PL intensity and decay time increased 3 and 2 times compared with ligand-free ZGO:AC PLNPs, respectively. Density functional theory (DFT) calculations and detailed characterizations demonstrated that surface quenching is suppressed due to the coordination of non-saturated Ga ions and -COO<sup>-</sup> of ligands. Finally, ZGO:AC@PA PLNPs were applied in autofluorescence-free bioimaging and exhibited high imaging sensitivity and contrast ratio. These findings provide insights into the surface quenching mechanisms of PLNPs and offer a platform for developing highly emissive PLNPs on nanoscale.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112477"},"PeriodicalIF":4.1,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420095","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

A dual-targeted small-molecule photosensitizer with enhanced dual antitumor and anti-vascular effect for metastatic advanced prostate cancer photodynamic therapy 用于转移性晚期前列腺癌光动力疗法的具有增强抗肿瘤和抗血管双重作用的双靶向小分子光敏剂

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-10-02 DOI: 10.1016/j.dyepig.2024.112476

Juanjuan Chen , Jiaqi Xu , Qilu Wang , Feifei Lin , Xueqing Zhang , Lirui Tang , Jinping Xue , Jinluan Li

Advanced prostate cancer is regarded as a fatal disease, characterized by limited treatment options, poor prognosis and considerable tumor metastasis closely related to angiogenesis. Photodynamic therapy emerges as a promising and safe therapeutic modality for advanced prostate cancer with high metastasis and high fatality rate due to its focal damage to tumor cells, as well as its anti-angiogenesis and antitumor immunity capabilities. Herein, a tumor-targeting vascular disrupting agent ASA-404 was introduced to conjugate with a photosensitizer ZnPc for targeted prostate cancer treatment and enhanced vascular-disrupting efficiency. Notably, this novel organic small-molecule photosensitizer Pc-ASA possess a well-defined chemical structure and purity, as well as good photophysical and photochemical properties, which are of benefit for clinical approval and application. Pc-ASA prefers to accumulate in both prostate cancer cells and vascular endothelial cells. Moreover, the conjugation of ASA-404 boosts the photodynamic anticancer effect of Pc-ASA towards both prostate cancer cells and vascular endothelial cells. Ultimately, PC-ASA can successfully inhibit the migration and metastasis of prostate cancer cells, offering significant advantages in advanced prostate cancer management. Our study might open a window in the development of the tumor and vascular dual-targeted small-molecule photosensitizers, with the potential to achieve safe and efficient treatment of metastatic advanced prostate cancer through dual mode of antitumor and anti-vascular action.

晚期前列腺癌被认为是一种致命疾病，其特点是治疗方案有限、预后不佳以及与血管生成密切相关的大量肿瘤转移。光动力疗法因其对肿瘤细胞的局灶性损伤，以及抗血管生成和抗肿瘤免疫能力，成为治疗高转移率和高致死率的晚期前列腺癌的一种前景广阔且安全的治疗方式。本文介绍了一种肿瘤靶向血管破坏剂 ASA-404 与光敏剂 ZnPc 共轭，用于前列腺癌靶向治疗并提高血管破坏效率。值得注意的是，这种新型有机小分子光敏剂 Pc-ASA 具有明确的化学结构和纯度，以及良好的光物理和光化学性质，有利于临床批准和应用。Pc-ASA 可在前列腺癌细胞和血管内皮细胞中积聚。此外，ASA-404 的共轭还能增强 Pc-ASA 对前列腺癌细胞和血管内皮细胞的光动力抗癌效果。最终，PC-ASA 能成功抑制前列腺癌细胞的迁移和转移，在晚期前列腺癌的治疗中具有显著优势。我们的研究可能会为肿瘤和血管双靶向小分子光敏剂的开发打开一扇窗，有望通过抗肿瘤和抗血管双重作用模式实现对转移性晚期前列腺癌的安全高效治疗。

{"title":"A dual-targeted small-molecule photosensitizer with enhanced dual antitumor and anti-vascular effect for metastatic advanced prostate cancer photodynamic therapy","authors":"Juanjuan Chen , Jiaqi Xu , Qilu Wang , Feifei Lin , Xueqing Zhang , Lirui Tang , Jinping Xue , Jinluan Li","doi":"10.1016/j.dyepig.2024.112476","DOIUrl":"10.1016/j.dyepig.2024.112476","url":null,"abstract":"<div><div>Advanced prostate cancer is regarded as a fatal disease, characterized by limited treatment options, poor prognosis and considerable tumor metastasis closely related to angiogenesis. Photodynamic therapy emerges as a promising and safe therapeutic modality for advanced prostate cancer with high metastasis and high fatality rate due to its focal damage to tumor cells, as well as its anti-angiogenesis and antitumor immunity capabilities. Herein, a tumor-targeting vascular disrupting agent ASA-404 was introduced to conjugate with a photosensitizer ZnPc for targeted prostate cancer treatment and enhanced vascular-disrupting efficiency. Notably, this novel organic small-molecule photosensitizer <strong>Pc-ASA</strong> possess a well-defined chemical structure and purity, as well as good photophysical and photochemical properties, which are of benefit for clinical approval and application. <strong>Pc-ASA</strong> prefers to accumulate in both prostate cancer cells and vascular endothelial cells. Moreover, the conjugation of ASA-404 boosts the photodynamic anticancer effect of <strong>Pc-ASA</strong> towards both prostate cancer cells and vascular endothelial cells. Ultimately, <strong>PC-ASA</strong> can successfully inhibit the migration and metastasis of prostate cancer cells, offering significant advantages in advanced prostate cancer management. Our study might open a window in the development of the tumor and vascular dual-targeted small-molecule photosensitizers, with the potential to achieve safe and efficient treatment of metastatic advanced prostate cancer through dual mode of antitumor and anti-vascular action.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112476"},"PeriodicalIF":4.1,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420096","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Design, synthesis and characterization of triphenylamine-based conjugated porous polymers as fluorescent receptors for nitroaromatic derivatives 作为硝基芳香族衍生物荧光受体的三苯胺基共轭多孔聚合物的设计、合成和表征

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-09-27 DOI: 10.1016/j.dyepig.2024.112470

Loredana Vacareanu, Andra-Elena Bejan, Dana Bejan, Petronela Pascariu, Mariana-Dana Damaceanu

Two series of hyperbranched conjugated polymers were synthesized via straightforward oxidative coupling polymerization, starting from star-shaped triphenylamine compounds with different internal π-spacers, each varying through the electron-withdrawing properties and rigidity. Excellent total reaction yields were achieved, exceeding 80 % under emulsion reaction conditions, particularly when employing compounds with high electron-withdrawing character (-CN). The polymers containing p-phenylene-vinylene and mixed p-phenylene (vinylene)-ethynylene structures were obtained predominantly as insoluble powders, mainly due to their fully aromatic backbone structure or highly cross-linked formed networks, and their chemical structures were validated by FT-IR analysis. Optical studies revealed that polymers synthesized under classical reaction conditions exhibited enhanced π-conjugation compared to those obtained via emulsion oxidative conditions, which was clearly reflected in a red-shift of the absorption and emission maxima. Conversely, the use of surfactants along with planar and rigid triple bonds facilitated the formation of more porous polymer networks, with the highest specific surface areas of 492 m²g^-1, compared to analogous networks based on vinylene hyperbranched polymers (99 m²g^-1) and (cyano)vinylene hyperbranched polymers (44 m²g^-1). The fluorescence emission of these polymers as solid dispersions in chloroform, although of low intensity for the CN-containing polymers, enables them to detect the nitro-aromatic derivatives via fluorescence quenching. The dependence of both detection limit and emission quenching efficiency on the polymers backbone structure and employed synthesis method was obvious. Notably, the Stern-Volmer quenching constant (K_SV) was highest for TNP, reaching 17.9 × 10³ M^-1 in the case of p-phenylene-vinylene polymer synthesized under emulsion reaction conditions, indicating promising avenues for the development of solid-state fluorescence sensors.

我们通过直接氧化偶联聚合反应合成了两个系列的超支化共轭聚合物，这些聚合物以具有不同内部π-间隔的星形三苯胺化合物为起点，每种化合物的吸电子特性和刚性各不相同。在乳液反应条件下，特别是在使用具有高吸电子特性（-CN）的化合物时，反应总产率超过 80%。含有对亚苯基-乙烯和混合对亚苯基（乙烯）-乙炔结构的聚合物主要以不溶性粉末的形式获得，这主要是由于它们具有全芳香族骨架结构或高度交联形成的网络。光学研究表明，与通过乳液氧化条件合成的聚合物相比，在传统反应条件下合成的聚合物表现出更强的π-共轭作用，这明显反映在吸收和发射最大值的红移上。相反，与基于乙烯超支化聚合物（99 m2g-1）和（氰基）乙烯超支化聚合物（44 m2g-1）的类似网络相比，使用表面活性剂以及平面和刚性三键有助于形成更多孔的聚合物网络，最高比表面积为 492 m2g-1。虽然含 CN 的聚合物在氯仿中的固体分散体的荧光发射强度较低，但它们能够通过荧光淬灭来检测硝基芳香族衍生物。检测限和发射淬灭效率对聚合物骨架结构和合成方法的依赖性显而易见。值得注意的是，在乳液反应条件下合成的对苯乙烯-乙烯聚合物中，TNP 的斯特恩-沃尔默淬灭常数（KSV）最高，达到 17.9 × 103 M-1，这表明固态荧光传感器的开发前景广阔。

{"title":"Design, synthesis and characterization of triphenylamine-based conjugated porous polymers as fluorescent receptors for nitroaromatic derivatives","authors":"Loredana Vacareanu, Andra-Elena Bejan, Dana Bejan, Petronela Pascariu, Mariana-Dana Damaceanu","doi":"10.1016/j.dyepig.2024.112470","DOIUrl":"10.1016/j.dyepig.2024.112470","url":null,"abstract":"<div><div>Two series of hyperbranched conjugated polymers were synthesized <em>via</em> straightforward oxidative coupling polymerization, starting from star-shaped triphenylamine compounds with different internal π-spacers, each varying through the electron-withdrawing properties and rigidity. Excellent total reaction yields were achieved, exceeding 80 % under emulsion reaction conditions, particularly when employing compounds with high electron-withdrawing character (-CN). The polymers containing <em>p</em>-phenylene-vinylene and mixed <em>p</em>-phenylene (vinylene)-ethynylene structures were obtained predominantly as insoluble powders, mainly due to their fully aromatic backbone structure or highly cross-linked formed networks, and their chemical structures were validated by FT-IR analysis. Optical studies revealed that polymers synthesized under classical reaction conditions exhibited enhanced π-conjugation compared to those obtained <em>via</em> emulsion oxidative conditions, which was clearly reflected in a red-shift of the absorption and emission maxima. Conversely, the use of surfactants along with planar and rigid triple bonds facilitated the formation of more porous polymer networks, with the highest specific surface areas of 492 m<sup>2</sup>g<sup>-1</sup>, compared to analogous networks based on vinylene hyperbranched polymers (99 m<sup>2</sup>g<sup>-1</sup>) and (cyano)vinylene hyperbranched polymers (44 m<sup>2</sup>g<sup>-1</sup>). The fluorescence emission of these polymers as solid dispersions in chloroform, although of low intensity for the CN-containing polymers, enables them to detect the nitro-aromatic derivatives <em>via</em> fluorescence quenching. The dependence of both detection limit and emission quenching efficiency on the polymers backbone structure and employed synthesis method was obvious. Notably, the Stern-Volmer quenching constant (K<sub>SV</sub>) was highest for TNP, reaching 17.9 × 10<sup>3</sup> M<sup>-1</sup> in the case of <em>p</em>-phenylene-vinylene polymer synthesized under emulsion reaction conditions, indicating promising avenues for the development of solid-state fluorescence sensors.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112470"},"PeriodicalIF":4.1,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420083","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Photo-modulation of the two-photon excited fluorescence of dithienylethene bis-(1-pyrenyl) compounds: An experimental and theoretical study 二噻吩双(1-芘基)化合物的双光子激发荧光的光调制：实验和理论研究

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-09-27 DOI: 10.1016/j.dyepig.2024.112473

Marie Barale, Iulia Turcas, Violette Gousseau, Muriel Escadeillas, Elsa Caytan, Gregory Taupier, Yann Molard, Arnaud Fihey, Julien Boixel

Photomodulation of two-photon excited fluorescence has been effectively controlled in 1-pyrene-based dithienylethenes. The specific molecular design enables photocommutation of two-photon excited fluorescence during sequential one- and two-photon excitations without interference nor destructive optical readout. Theoretical studies have concluded that the internal functionalization of pyrene is responsible for the photoactivity in these systems. Photophysical studies indicate that the presence of a second laterally introduced pyrene is crucial for maintaining high photocommutation contrast and durability.

双光子激发荧光的光调节已被有效地控制在以 1-pyrene 为基础的二噻吩中。特定的分子设计使双光子激发的荧光在连续的单光子和双光子激发过程中发生光致变换，而不会产生干扰或破坏性的光学读数。理论研究认为，芘的内部官能化是这些系统产生光活性的原因。光物理研究表明，第二个横向引入的芘的存在对于保持高光致变换对比度和耐久性至关重要。

引用次数: 0

Design and synthesis of heterocycle-based push-pull NLOphores: A comprehensive study of their linear and non-linear optical properties 基于杂环的推挽式 NLOphores 的设计与合成：对其线性和非线性光学特性的全面研究

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-09-27 DOI: 10.1016/j.dyepig.2024.112469

Başak Karagöllü , Tolga Orçun Şengöz , Hazal Kayaş , Kübra Erden , Ertan Şahin , Okan Esenturk , Cagatay Dengiz

Push-pull chromophores, with strong intramolecular charge transfer (ICT), exhibit high ground-state polarization, driving strong NLO responses. The donor and acceptor abilities of the groups in the investigated compounds influence ICT, so the nonlinear response of these compounds was analyzed in relation to their strength. Two different families of NLOphores were synthesized through [2 + 2] cycloaddition-retroelectrocyclizations of heterocycle-based electron-rich alkynes with tetracyanoethylene (TCNE) and tetracyanoquinodimethane (TCNQ). The λ_max values of push-pull chromophores, particularly for charge transfer bands, fall within the range of 424–758 nm. The linear and nonlinear optical properties of these NLOphores were subsequently examined through a combination of experimental and theoretical methods. NLO measurements were conducted using a validated custom-made Z-scan device. The nonlinear absorption coefficients range from −1.44 × 10⁻⁴ cm.W⁻¹ to −9.90 × 10⁻⁴ cm.W⁻¹, while nonlinear refractive indices range from −1.59 × 10⁻⁷ cm². W⁻¹ to −2.26 × 10⁻⁶ cm². W⁻¹. As expected from their molecular structures, the TCNQ products displayed stronger nonlinear responses than the TCNE products.

推拉型发色团具有很强的分子内电荷转移（ICT），表现出很高的基态极化，从而产生很强的非线性响应。所研究化合物中基团的供体和受体能力会影响 ICT，因此我们分析了这些化合物的非线性响应与 ICT 强度的关系。通过杂环基富电子炔与四氰基乙烯（TCNE）和四氰基二甲基醌（TCNQ）的[2 + 2]环加成-逆电环合成了两个不同系列的 NLOphores。推拉发色团的 λmax 值，尤其是电荷转移带，在 424-758 纳米范围内。随后，结合实验和理论方法对这些 NLO 色素的线性和非线性光学特性进行了研究。NLO 测量是使用经过验证的定制 Z 扫描装置进行的。非线性吸收系数从 -1.44 × 10-4 cm.W-1 到 -9.90 × 10-4 cm.W-1，而非线性折射率则从 -1.59 × 10-7 cm2.W-1 到 -2.26 × 10-6 cm2.W-1.正如其分子结构所预期的那样，TCNQ 产品比 TCNE 产品显示出更强的非线性响应。

{"title":"Design and synthesis of heterocycle-based push-pull NLOphores: A comprehensive study of their linear and non-linear optical properties","authors":"Başak Karagöllü , Tolga Orçun Şengöz , Hazal Kayaş , Kübra Erden , Ertan Şahin , Okan Esenturk , Cagatay Dengiz","doi":"10.1016/j.dyepig.2024.112469","DOIUrl":"10.1016/j.dyepig.2024.112469","url":null,"abstract":"<div><div>Push-pull chromophores, with strong intramolecular charge transfer (ICT), exhibit high ground-state polarization, driving strong NLO responses. The donor and acceptor abilities of the groups in the investigated compounds influence ICT, so the nonlinear response of these compounds was analyzed in relation to their strength. Two different families of NLOphores were synthesized through [2 + 2] cycloaddition-retroelectrocyclizations of heterocycle-based electron-rich alkynes with tetracyanoethylene (TCNE) and tetracyanoquinodimethane (TCNQ). The <em>λ</em><sub>max</sub> values of push-pull chromophores, particularly for charge transfer bands, fall within the range of 424–758 nm. The linear and nonlinear optical properties of these NLOphores were subsequently examined through a combination of experimental and theoretical methods. NLO measurements were conducted using a validated custom-made Z-scan device. The nonlinear absorption coefficients range from −1.44 × 10<sup>−4</sup> cm.W<sup>−1</sup> to −9.90 × 10<sup>−4</sup> cm.W<sup>−1</sup>, while nonlinear refractive indices range from −1.59 × 10<sup>−7</sup> cm<sup>2</sup>. W<sup>−1</sup> to −2.26 × 10<sup>−6</sup> cm<sup>2</sup>. W<sup>−1</sup>. As expected from their molecular structures, the TCNQ products displayed stronger nonlinear responses than the TCNE products.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112469"},"PeriodicalIF":4.1,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420094","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0