Pub Date : 2024-11-05DOI: 10.1016/j.dyepig.2024.112533
Vivian Nketia-Yawson , Hae Jeong Kim , Hyungju Ahn , Benjamin Nketia-Yawson , Jongmin Choi , Jea Woong Jo
With the tunability of their electronic properties, π-conjugated polymeric semiconductors have been extensively researched for electronic devices. Here, benzo [1,2-b:4,5-b′]dithiophene-based conjugated polymers are synthesized by controlling the contents of thiophene and furan units and their electrical characteristics are reported. The synthesized furan-containing polymers exhibited smoother surface morphology, desirable solubility, deeper highest occupied molecular orbital levels, increased band gap, and improved film crystallinity. The electrolyte-gated organic field-effect transistors using 25 % furan substituted polymer, P2, exhibited a high mobility of over 8 cm2 V−1 s−1. Furthermore, AgBiS2 nanocrystal photovoltaics using P2 as a hole transport material provided a higher efficiency of 5.59 % compared to devices using control polymer without furan substitution (4.30 %). Our work demonstrates significant structure-property relationships for modifying the electrical properties of polymer semiconductors using molecular engineering to achieve high-performing organic electronic devices.
{"title":"Furan-substituted benzodithiophene-based polymer semiconductors as charge transport materials for organic transistors and nanocrystal photovoltaics","authors":"Vivian Nketia-Yawson , Hae Jeong Kim , Hyungju Ahn , Benjamin Nketia-Yawson , Jongmin Choi , Jea Woong Jo","doi":"10.1016/j.dyepig.2024.112533","DOIUrl":"10.1016/j.dyepig.2024.112533","url":null,"abstract":"<div><div>With the tunability of their electronic properties, π-conjugated polymeric semiconductors have been extensively researched for electronic devices. Here, benzo [1,2-<em>b</em>:4,5-<em>b</em>′]dithiophene-based conjugated polymers are synthesized by controlling the contents of thiophene and furan units and their electrical characteristics are reported. The synthesized furan-containing polymers exhibited smoother surface morphology, desirable solubility, deeper highest occupied molecular orbital levels, increased band gap, and improved film crystallinity. The electrolyte-gated organic field-effect transistors using 25 % furan substituted polymer, <strong>P2</strong>, exhibited a high mobility of over 8 cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>. Furthermore, AgBiS<sub>2</sub> nanocrystal photovoltaics using <strong>P2</strong> as a hole transport material provided a higher efficiency of 5.59 % compared to devices using control polymer without furan substitution (4.30 %). Our work demonstrates significant structure-property relationships for modifying the electrical properties of polymer semiconductors using molecular engineering to achieve high-performing organic electronic devices.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112533"},"PeriodicalIF":4.1,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656349","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}
Pub Date : 2024-11-05DOI: 10.1016/j.dyepig.2024.112534
Sumit Kumar Patra, Ramalingam Manivannan, Young-A Son
In several practical sectors, it has been demonstrated that multistate emissive materials have far wider applications than single state emissive fluorophore materials; yet, this remains an extremely challenging undertaking. It has been thought that adding rigid and twisted moieties to the D-A-D core will be appropriate to allow for both solid state and solution emission. By developing a donor-acceptor-donor pattern in a twisted molecule, herein we design and synthesize triphenylamine based two novel luminogens MSE1 and MSE2 with dual-state emission (DSEgens) which are brilliantly luminous equally at the liquid and solid phase, with positive solvatochromic features. The triphenylamine molecule's bulkiness can limit intramolecular movement in the liquid phase, thereby diminishing the non-radiative emission. Additionally, the twisted structure of the molecule reduce the negative effects of close π-π stacking in the solid state resulting high emission at aggregated state. In poor solvent like H2O and extremely condensed solvent like polyethylene glycol, compound MSE1 and MSE2 exhibit aggregation-caused redshift emission (ACRE), which are supported by DLS and SEM investigations. The compound MSE1 in THF solution is able to recognize mercury selectively over other competitive cation through UV–vis and fluorescence channel. An eight fold suppression of fluorescence intensity and a change in absorbance of 115 nm were noted at the addition of 0–8 equivalent mercury to MSE1. Additionally, MSE1 has been used to create a low-cost, portable test paper strip that may be used to selectively monitor mercury in real time.
{"title":"Multi-state efficient luminogens with solvatochromic features based on a conjugation induced twisted framework for highly selective dual channel detection of mercury ion","authors":"Sumit Kumar Patra, Ramalingam Manivannan, Young-A Son","doi":"10.1016/j.dyepig.2024.112534","DOIUrl":"10.1016/j.dyepig.2024.112534","url":null,"abstract":"<div><div>In several practical sectors, it has been demonstrated that multistate emissive materials have far wider applications than single state emissive fluorophore materials; yet, this remains an extremely challenging undertaking. It has been thought that adding rigid and twisted moieties to the D-A-D core will be appropriate to allow for both solid state and solution emission. By developing a donor-acceptor-donor pattern in a twisted molecule, herein we design and synthesize triphenylamine based two novel luminogens <strong>MSE1</strong> and <strong>MSE2</strong> with dual-state emission (DSEgens) which are brilliantly luminous equally at the liquid and solid phase, with positive solvatochromic features. The triphenylamine molecule's bulkiness can limit intramolecular movement in the liquid phase, thereby diminishing the non-radiative emission. Additionally, the twisted structure of the molecule reduce the negative effects of close π-π stacking in the solid state resulting high emission at aggregated state. In poor solvent like H<sub>2</sub>O and extremely condensed solvent like polyethylene glycol, compound <strong>MSE1</strong> and <strong>MSE2</strong> exhibit aggregation-caused redshift emission (ACRE), which are supported by DLS and SEM investigations. The compound <strong>MSE1</strong> in THF solution is able to recognize mercury selectively over other competitive cation through UV–vis and fluorescence channel. An eight fold suppression of fluorescence intensity and a change in absorbance of 115 nm were noted at the addition of 0–8 equivalent mercury to <strong>MSE1</strong>. Additionally, <strong>MSE1</strong> has been used to create a low-cost, portable test paper strip that may be used to selectively monitor mercury in real time.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112534"},"PeriodicalIF":4.1,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656389","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}
Pub Date : 2024-11-05DOI: 10.1016/j.dyepig.2024.112530
Michael Gerlach , Justus Koedel , Sebastian Seibt , Benjamin Baumgärtner , Christoph Callsen , Gundula Voss , Florian Puchtler , Andy Weidinger , Georg Puchas , Daniel Leykam , Volker Altstaedt , Rainer Schobert , Holger Ruckdäschel , Bernhard Biersack
A small series of indigo derivatives were mixed with palygorskite or sepiolite, respectively, and heated at 150 °C overnight in order to prepare stable pigments. While mixtures with violet halo-indigos such as Tyrian Purple (6,6′-dibromoindigo) and its difluoro- and dichloro-derivatives formed blue pigments with a slight greenish hue upon heating, alkoxy-indigo derivatives turned olive green during the heating process when mixed with palygorskite or sepiolite. Mixtures of isatin and indigo with palygorsite led to the formation of green pigments. The pigments were analyzed by spectroscopy (UV-VIS and Raman) and electron microscopy. Thermal studies were carried out and the obtained pigments were stable at temperatures of up to 250 °C. Maya Blue and pigment samples derived from 6,6′-dichloroindigo were tested for their flame retarding properties in mixtures with cellulose acetate and both additives led to distinct heat release rate reductions.
为了制备稳定的颜料，我们将一系列靛蓝衍生物分别与堇青石或霞石混合，并在 150 °C 下加热过夜。与紫色卤代靛蓝（如泰里安紫（6,6′-二溴靛蓝）及其二氟和二氯衍生物）的混合物在加热后会形成略带绿色的蓝色颜料，而烷氧基靛蓝衍生物在与堇青石或海泡石混合后，在加热过程中会变成橄榄绿色。将异靛蓝和靛蓝与白云母混合可形成绿色颜料。这些颜料通过光谱（紫外-可见光谱和拉曼光谱）和电子显微镜进行了分析。进行了热研究，结果表明所获得的颜料在高达 250 ℃ 的温度下都很稳定。测试了玛雅蓝和从 6,6′-二氯靛蓝中提取的颜料样品在与醋酸纤维素混合物中的阻燃性能，两种添加剂都明显降低了热释放率。
{"title":"The influence of substituted indigo derivatives on the preparation and properties of “Maya” pigments","authors":"Michael Gerlach , Justus Koedel , Sebastian Seibt , Benjamin Baumgärtner , Christoph Callsen , Gundula Voss , Florian Puchtler , Andy Weidinger , Georg Puchas , Daniel Leykam , Volker Altstaedt , Rainer Schobert , Holger Ruckdäschel , Bernhard Biersack","doi":"10.1016/j.dyepig.2024.112530","DOIUrl":"10.1016/j.dyepig.2024.112530","url":null,"abstract":"<div><div>A small series of indigo derivatives were mixed with palygorskite or sepiolite, respectively, and heated at 150 °C overnight in order to prepare stable pigments. While mixtures with violet halo-indigos such as Tyrian Purple (6,6′-dibromoindigo) and its difluoro- and dichloro-derivatives formed blue pigments with a slight greenish hue upon heating, alkoxy-indigo derivatives turned olive green during the heating process when mixed with palygorskite or sepiolite. Mixtures of isatin and indigo with palygorsite led to the formation of green pigments. The pigments were analyzed by spectroscopy (UV-VIS and Raman) and electron microscopy. Thermal studies were carried out and the obtained pigments were stable at temperatures of up to 250 °C. Maya Blue and pigment samples derived from 6,6′-dichloroindigo were tested for their flame retarding properties in mixtures with cellulose acetate and both additives led to distinct heat release rate reductions.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112530"},"PeriodicalIF":4.1,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656350","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-05DOI: 10.1016/j.dyepig.2024.112532
Wen-Hao Zhang , Dian Luo , Jin-San Shih , Lin-Ming Huang , Shu-Wan Peng , Chih-Chien Lee , Shun-Wei Liu , Chih-Hsin Chen
This study explores the development of cyano-substituted bis((benzothiophen-2-yl)pyridine) (acetylacetonate) iridium complexes, specifically Ir(btpCN)2(acac), for use in efficient and stable deep red organic light-emitting diodes (OLEDs) emitting at 673 nm. The new emitter, Ir(btpCN)2(acac), was designed to achieve red-shifted emission through strategic cyano substitution at the meta-position of pyridine moiety of btp ligand, leveraging the favorable overlap between its emission spectrum and the absorption spectrum of the exciplex host composed of BCzPh and CN-T2T. The OLED devices employing Ir(btpCN)2(acac) as the emitter exhibited a peak external quantum efficiency (EQE) of 10.2 % and an emission wavelength of 673 nm. Significantly, these devices demonstrated superior operational stability, with a lifetime (LT50) of 190.8 h at an initial luminance of 200 cd m−2, which is among the highest reported for deep-red OLEDs in the literature. This remarkable stability is achieved without compromising the device performance, making Ir(btpCN)2(acac) a highly promising candidate for commercial applications. In addition, the straightforward synthesis process of Ir(btpCN)2(acac) further enhances its potential for widespread use. Overall, our findings highlight the potential of cyano-substituted Ir complexes for creating efficient, stable, and commercially viable deep-red OLEDs. The balanced performance of Ir(btpCN)2(acac) in terms of efficiency, stability, and ease of synthesis marks a significant advancement in the development of OLED technology suitable for phototherapy and other applications requiring reliable deep-red light sources.
{"title":"Cyano-substituted Bis((benzothiophen-2-yl)pyridine) (acetylacetonate) iridium complexes for efficient and stable deep red organic light-emitting diodes emitting at 673 nm","authors":"Wen-Hao Zhang , Dian Luo , Jin-San Shih , Lin-Ming Huang , Shu-Wan Peng , Chih-Chien Lee , Shun-Wei Liu , Chih-Hsin Chen","doi":"10.1016/j.dyepig.2024.112532","DOIUrl":"10.1016/j.dyepig.2024.112532","url":null,"abstract":"<div><div>This study explores the development of cyano-substituted bis((benzothiophen-2-yl)pyridine) (acetylacetonate) iridium complexes, specifically Ir(btpCN)<sub>2</sub>(acac), for use in efficient and stable deep red organic light-emitting diodes (OLEDs) emitting at 673 nm. The new emitter, Ir(btpCN)<sub>2</sub>(acac), was designed to achieve red-shifted emission through strategic cyano substitution at the meta-position of pyridine moiety of btp ligand, leveraging the favorable overlap between its emission spectrum and the absorption spectrum of the exciplex host composed of BCzPh and CN-T2T. The OLED devices employing Ir(btpCN)<sub>2</sub>(acac) as the emitter exhibited a peak external quantum efficiency (EQE) of 10.2 % and an emission wavelength of 673 nm. Significantly, these devices demonstrated superior operational stability, with a lifetime (LT<sub>50</sub>) of 190.8 h at an initial luminance of 200 cd m<sup>−2</sup>, which is among the highest reported for deep-red OLEDs in the literature. This remarkable stability is achieved without compromising the device performance, making Ir(btpCN)<sub>2</sub>(acac) a highly promising candidate for commercial applications. In addition, the straightforward synthesis process of Ir(btpCN)<sub>2</sub>(acac) further enhances its potential for widespread use. Overall, our findings highlight the potential of cyano-substituted Ir complexes for creating efficient, stable, and commercially viable deep-red OLEDs. The balanced performance of Ir(btpCN)<sub>2</sub>(acac) in terms of efficiency, stability, and ease of synthesis marks a significant advancement in the development of OLED technology suitable for phototherapy and other applications requiring reliable deep-red light sources.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112532"},"PeriodicalIF":4.1,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656348","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}
Pub Date : 2024-11-04DOI: 10.1016/j.dyepig.2024.112531
Ji Xiong , Ming-Hui Chen , Xiang-Yu Li , Quan Shi , Yun-Hao Xu , Ya-Qing Feng , Bao Zhang
The sunlight-driven CO2 fixation into high value-added industrial products constitutes a promising approach to mitigating global warming, offering an alternative to traditional thermally-driven fixation requiring high temperature and/or high pressure. Herein, we design and synthesize four isostructural porphyrinic covalent triazine frameworks (Por-CTFs) including metal-free Por-CTF (H2Por-CTF) and metallized Por-CTFs (MPor-CTFs, M = Co, Zn, Cu) and their photocatalytic activity in CO2 cycloaddition. All Por-CTFs exhibit wide light adsorption range in visible region via introducing porphyrins into the covalent triazine frameworks (CTFs) skeleton. Different metal ions which are well anchored in the MPor-CTFs skeleton not only offer Lewis acidic sites for substrate interaction but also apparently endow photocatalysts with longer photogenerated carrier lifetimes and higher electron-hole separation efficiency. Encouragingly, under visible light-assisted and mild conditions, the CoPor-CTF exhibits excellent photocatalytic performance achieving a reaction rate of 62.22 mmol g−1 h−1, which is among the state-of-the-art cases for photocatalytic CO2 cycloaddition and outperforms two other MPor-CTFs. This work demonstrates that the photophysical and electronic properties of Por-CTFs can be rationally tuned by incorporating various metal ions into porphyrin units to achieve effective photocatalysts for CO2 cycloaddition.
{"title":"Metalloporphyrin-based covalent triazine frameworks for efficient photocatalytic CO2 cycloaddition at ambient conditions","authors":"Ji Xiong , Ming-Hui Chen , Xiang-Yu Li , Quan Shi , Yun-Hao Xu , Ya-Qing Feng , Bao Zhang","doi":"10.1016/j.dyepig.2024.112531","DOIUrl":"10.1016/j.dyepig.2024.112531","url":null,"abstract":"<div><div>The sunlight-driven CO<sub>2</sub> fixation into high value-added industrial products constitutes a promising approach to mitigating global warming, offering an alternative to traditional thermally-driven fixation requiring high temperature and/or high pressure. Herein, we design and synthesize four isostructural porphyrinic covalent triazine frameworks (<strong>Por-CTFs</strong>) including metal-free <strong>Por-CTF</strong> (<strong>H2Por-CTF</strong>) and metallized <strong>Por-CTFs</strong> (<strong>MPor-CTFs</strong>, M = Co, Zn, Cu) and their photocatalytic activity in CO<sub>2</sub> cycloaddition. All <strong>Por-CTFs</strong> exhibit wide light adsorption range in visible region via introducing porphyrins into the covalent triazine frameworks (CTFs) skeleton. Different metal ions which are well anchored in the <strong>MPor-CTFs</strong> skeleton not only offer Lewis acidic sites for substrate interaction but also apparently endow photocatalysts with longer photogenerated carrier lifetimes and higher electron-hole separation efficiency. Encouragingly, under visible light-assisted and mild conditions, the <strong>CoPor-CTF</strong> exhibits excellent photocatalytic performance achieving a reaction rate of 62.22 mmol g<sup>−1</sup> h<sup>−1</sup>, which is among the state-of-the-art cases for photocatalytic CO<sub>2</sub> cycloaddition and outperforms two other <strong>MPor-CTFs</strong>. This work demonstrates that the photophysical and electronic properties of <strong>Por-CTFs</strong> can be rationally tuned by incorporating various metal ions into porphyrin units to achieve effective photocatalysts for CO<sub>2</sub> cycloaddition.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112531"},"PeriodicalIF":4.1,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142587022","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}
A porphyrin (H2P) and a porphyrazine (H2Pz) and their respective zinc complexes (ZnP and ZnPz), with the substituent N-ethylpyridyl-3-yl, were synthesized and their photophysical and phototoxic properties were compared. These substances showed high solubility in water due to the cationic moieties and without notable aggregation in this solvent. Photophysical studies showed that H2P and H2Pz have fluorescence quantum yields (ΦF) of 2.04 % and 0.48 % in water, respectively, that, upon metalation, decreases to 1.4 % for the metalloporphyrin (ZnP) and increases to 6.1 % for the metalloporphyrazine (ZnPz). Regarding the singlet oxygen production efficiency (ΦΔ) of the substances in water, a considerable increase from 16.2 % to 41 % was obtained for the porphyrin upon coordination to zinc, while the porphyrazines practically do not produce singlet oxygen (<1 %) in this solvent. When tested against human squamous cell carcinoma cells (A-431) and immortalized human keratinocytes (HaCaT), the toxicity of all compounds increased using green (520 ± 5 nm) and red (625 ± 5 nm) radiation when compared to the non-irradiated cells, however, phototoxicity was higher for the porphyrins using green light, while the porphyrazines performed better under red radiation. Furthermore, porphyrins had a higher phototoxic index than porphyrazines and greater selectivity for A-431 cancer cells compared to HaCaT cells. To the best of our knowledge, this is the first work that compares the photophysical response and in vitro anticancer activity of porphyrins and porphyrazines with the same substituent.
{"title":"Structurally similar porphyrins and porphyrazines perform differently under green or red light irradiation against non-melanoma skin tumor cells","authors":"Gustavo Wander Streit, Heveline Silva, Thiago Teixeira Tasso, Gilson DeFreitas-Silva","doi":"10.1016/j.dyepig.2024.112527","DOIUrl":"10.1016/j.dyepig.2024.112527","url":null,"abstract":"<div><div>A porphyrin (H<sub>2</sub>P) and a porphyrazine (H<sub>2</sub>Pz) and their respective zinc complexes (ZnP and ZnPz), with the substituent <em>N</em>-ethylpyridyl-3-yl, were synthesized and their photophysical and phototoxic properties were compared. These substances showed high solubility in water due to the cationic moieties and without notable aggregation in this solvent. Photophysical studies showed that H<sub>2</sub>P and H<sub>2</sub>Pz have fluorescence quantum yields (Φ<sub>F</sub>) of 2.04 % and 0.48 % in water, respectively, that, upon metalation, decreases to 1.4 % for the metalloporphyrin (ZnP) and increases to 6.1 % for the metalloporphyrazine (ZnPz). Regarding the singlet oxygen production efficiency (Φ<sub>Δ</sub>) of the substances in water, a considerable increase from 16.2 % to 41 % was obtained for the porphyrin upon coordination to zinc, while the porphyrazines practically do not produce singlet oxygen (<1 %) in this solvent. When tested against human squamous cell carcinoma cells (A-431) and immortalized human keratinocytes (HaCaT), the toxicity of all compounds increased using green (520 ± 5 nm) and red (625 ± 5 nm) radiation when compared to the non-irradiated cells, however, phototoxicity was higher for the porphyrins using green light, while the porphyrazines performed better under red radiation. Furthermore, porphyrins had a higher phototoxic index than porphyrazines and greater selectivity for A-431 cancer cells compared to HaCaT cells. To the best of our knowledge, this is the first work that compares the photophysical response and in vitro anticancer activity of porphyrins and porphyrazines with the same substituent.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112527"},"PeriodicalIF":4.1,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656388","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}
Pub Date : 2024-10-30DOI: 10.1016/j.dyepig.2024.112525
Xinyu Lv , Ying Bao , Huimin Zhou, Yi Qu
Aggregation-induced emission/aggregation-induced emission enhancement (AIE/AIEE) luminogens provides amount of highly emissive materials in density states for versatile applications. Most of the AIE/AIEEgens were designed with the multiply rotation unit, in which the additional rotation units not only extend the molecular structure but also suffer from low atom economy. Herein, a fluorination strategy was introduced to construct ten AIE/AIEEgens with 1∼3 fluorine (F) atoms at different position of phenyl ring at previous developed AIEgen, 4-phenyl-1,8-naphthalimide, which can output tuning emissive wavelength and high quantum yields in both aqueous solutions and solids. In these compounds, five AIEgens with ortho-F atom and five AIEEgens without ortho-F atom were obtained. All compounds show bright blue emissions centered at 430–485 nm in aqueous solutions and wide emissions covering visible region in solid states. We calculated the ratio of quantum yields between their aqueous solution and THF solution (Φwater/ΦTHF). The AIE luminogens show the higher ratios between 10.19 and 24.89 and the AIEEgens show the lower ratios between 1.89 and 6.40. This strategy based on changing the substituent positions of F atoms provides an efficient and convenient method for construction of novel AIE-active materials with variable photophysical properties in density states.
聚集诱导发射/聚集诱导发射增强（AIE/AIEE）发光剂提供了大量密度状态下的高发射材料，可用于多种应用。大多数 AIE/AIEE 光源都是采用多旋转单元设计的，其中额外的旋转单元不仅扩展了分子结构，而且原子经济性较低。本文介绍了一种氟化策略，在先前开发的 AIEgen（4-苯基-1,8-萘二甲酰亚胺）的苯基环的不同位置上构建了 10 个含有 1∼3 个氟（F）原子的 AIE/AIEEgens，这些 AIE/AIEEgens 可在水溶液和固体中输出可调的发射波长和高量子产率。在这些化合物中，获得了五种带正交 F 原子的 AIEEgens 和五种不带正交 F 原子的 AIEEgens。所有化合物在水溶液中都会发出以 430-485 nm 为中心的明亮蓝光，而在固体状态下则会发出覆盖可见光区域的宽光谱。我们计算了其水溶液与 THF 溶液的量子产率比（Φwater/ΦTHF）。AIE发光剂的比值较高，在10.19和24.89之间，而AIEE发光剂的比值较低，在1.89和6.40之间。这种基于改变 F 原子取代基位置的策略为构建具有不同密度态光物理性质的新型 AIE 活性材料提供了一种高效便捷的方法。
{"title":"Mono-/multi-fluorination of 1,8-naphthalimides for developing AIE/AIEE fluorophores with tuning emission wavelength","authors":"Xinyu Lv , Ying Bao , Huimin Zhou, Yi Qu","doi":"10.1016/j.dyepig.2024.112525","DOIUrl":"10.1016/j.dyepig.2024.112525","url":null,"abstract":"<div><div>Aggregation-induced emission/aggregation-induced emission enhancement (AIE/AIEE) luminogens provides amount of highly emissive materials in density states for versatile applications. Most of the AIE/AIEEgens were designed with the multiply rotation unit, in which the additional rotation units not only extend the molecular structure but also suffer from low atom economy. Herein, a fluorination strategy was introduced to construct ten AIE/AIEEgens with 1∼3 fluorine (F) atoms at different position of phenyl ring at previous developed AIEgen, 4-phenyl-1,8-naphthalimide, which can output tuning emissive wavelength and high quantum yields in both aqueous solutions and solids. In these compounds, five AIEgens with ortho-F atom and five AIEEgens without ortho-F atom were obtained. All compounds show bright blue emissions centered at 430–485 nm in aqueous solutions and wide emissions covering visible region in solid states. We calculated the ratio of quantum yields between their aqueous solution and THF solution (Φ<sub>water</sub>/Φ<sub>THF</sub>). The AIE luminogens show the higher ratios between 10.19 and 24.89 and the AIEEgens show the lower ratios between 1.89 and 6.40. This strategy based on changing the substituent positions of F atoms provides an efficient and convenient method for construction of novel AIE-active materials with variable photophysical properties in density states.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112525"},"PeriodicalIF":4.1,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142593536","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}
Pub Date : 2024-10-29DOI: 10.1016/j.dyepig.2024.112523
Dopil Kim , Sangho Lee , Haein Kim , Jun Yeong Kim , Yoseph Kim , Youngjo Kim , Myung Hwan Park , Dokyoung Kim , Jaesung Kwak , Dongwook Kim , Min Kim
Recent advancements in the development of low molecular-weight fluorophores have led to the study of a single-benzene fluorophore (SBF) containing both electron-withdrawing and electron-donating groups within an aromatic ring, resulting in unique photophysical properties. In this study, we explored the modulation of emissions by adjusting the electron-donating properties via the simple methylation of the 2,5-diamino or 2,5-dihydroxy terephthalate structure. Introducing additional functional groups under both symmetrical and unsymmetrical conditions demonstrated changes in the photophysical properties, which was not only owing to the structural variations in the location and number of methyl groups but also due to alterations in the electron-donating properties. The observed effects appeared to be owing to the interactions between the amine and ester groups, as confirmed via single-crystal X-ray diffraction. Finally, hydrolysis of the ester to the corresponding carboxylic acid resulted in various emission wavelengths at different pH values via protonation and deprotonation. This study provides valuable insights for predicting the structural and electronic effects of additional functional groups in SBF.
{"title":"Structural and electronic tuning of single-benzene fluorophores with simple methylations","authors":"Dopil Kim , Sangho Lee , Haein Kim , Jun Yeong Kim , Yoseph Kim , Youngjo Kim , Myung Hwan Park , Dokyoung Kim , Jaesung Kwak , Dongwook Kim , Min Kim","doi":"10.1016/j.dyepig.2024.112523","DOIUrl":"10.1016/j.dyepig.2024.112523","url":null,"abstract":"<div><div>Recent advancements in the development of low molecular-weight fluorophores have led to the study of a single-benzene fluorophore (SBF) containing both electron-withdrawing and electron-donating groups within an aromatic ring, resulting in unique photophysical properties. In this study, we explored the modulation of emissions by adjusting the electron-donating properties via the simple methylation of the 2,5-diamino or 2,5-dihydroxy terephthalate structure. Introducing additional functional groups under both symmetrical and unsymmetrical conditions demonstrated changes in the photophysical properties, which was not only owing to the structural variations in the location and number of methyl groups but also due to alterations in the electron-donating properties. The observed effects appeared to be owing to the interactions between the amine and ester groups, as confirmed via single-crystal X-ray diffraction. Finally, hydrolysis of the ester to the corresponding carboxylic acid resulted in various emission wavelengths at different pH values via protonation and deprotonation. This study provides valuable insights for predicting the structural and electronic effects of additional functional groups in SBF.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112523"},"PeriodicalIF":4.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142571693","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}
Pub Date : 2024-10-29DOI: 10.1016/j.dyepig.2024.112524
Xinfeng Zhang , Nazeer Muhammad Nouman , Caixia Yin , Fangjun Huo
Ischemia-reperfusion injury is closely linked to oxidative stress, which arises from the complicated metabolism of substances and energy. There is a growing inclination towards developing and applying fluorescent probe tools to explore this phenomenon's physiological and pathological mechanisms. Starting from the pathophysiology of ischemia-reperfusion injury in various organs, this review will provide a comprehensive overview of the research advancements related to developing and applying fluorescence probes for studying ischemia-reperfusion diseases. We will examine the use of small molecule fluorescence probes in the context of ischemia-reperfusion in various tissues and organs. Our focus will include liver, brain, kidney, and myocardial ischemia-reperfusion and other related conditions. In addition, this comment will deeply reflect on and analyze the development direction of fluorescent probes for ischemia-reperfusion injury, highlighting their potential for accurate clinical diagnosis and application research. This discussion aims to inspire hope and optimism in the audience about the future of medical research.
{"title":"A review of the application of small organic molecule fluorescent probes in ischemia-reperfusion injury","authors":"Xinfeng Zhang , Nazeer Muhammad Nouman , Caixia Yin , Fangjun Huo","doi":"10.1016/j.dyepig.2024.112524","DOIUrl":"10.1016/j.dyepig.2024.112524","url":null,"abstract":"<div><div>Ischemia-reperfusion injury is closely linked to oxidative stress, which arises from the complicated metabolism of substances and energy. There is a growing inclination towards developing and applying fluorescent probe tools to explore this phenomenon's physiological and pathological mechanisms. Starting from the pathophysiology of ischemia-reperfusion injury in various organs, this review will provide a comprehensive overview of the research advancements related to developing and applying fluorescence probes for studying ischemia-reperfusion diseases. We will examine the use of small molecule fluorescence probes in the context of ischemia-reperfusion in various tissues and organs. Our focus will include liver, brain, kidney, and myocardial ischemia-reperfusion and other related conditions. In addition, this comment will deeply reflect on and analyze the development direction of fluorescent probes for ischemia-reperfusion injury, highlighting their potential for accurate clinical diagnosis and application research. This discussion aims to inspire hope and optimism in the audience about the future of medical research.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112524"},"PeriodicalIF":4.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142587023","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}
Pub Date : 2024-10-29DOI: 10.1016/j.dyepig.2024.112516
Weilin Zhang , Chen Duan , Jimin Du , Mengzhen Du , Xiaojun Li , Cong Li , Qiang Guo , Erjun Zhou
The design and synthesis of hole-transport materials (HTMs) is a hot research topic in perovskite solar cells (PSCs) community. Thanks to the continuous optimization of polymer structures, dopant-free polymers as HTMs have achieved rapid development in PSCs over the past few years. In this study, two D-A type polymers, PBQ6 and PBQ9, are selected as HTMs for CsPbI2Br all-inorganic PSCs. Both polymers have the same donor (D) unit of benzodithiophene (BDT) with fluorinated thiophene side chain, but different acceptor (A) unit, fluorinated thiophene for PBQ6 while chlorinated thiophene for PBQ9. Then, the impact of different halogen substitutions on the optical and electrical properties of the polymer HTMs and the photovoltaic performance are investigated. Compared to PBQ6, PBQ9 demonstrates better energy level alignment with CsPbI2Br, more efficient carrier extraction and transportation, and enhanced suppression of non-radiative losses. Consequently, CsPbI2Br PSCs based on PBQ9-HTM achieve a higher power conversion efficiency (PCE) of 16.41 % compared to those based on PBQ6-HTM, which exhibit a PCE of 14.93 %. This study underscores the rational side chain engineering on A unit for D-A type polymer can improve the performance of HTMs, thereby further enhancing the efficiency of PSCs.
{"title":"D-A type polymers based on quinoxaline unit containing halogenated thiophene side chain as hole transport materials for efficient CsPbI2Br perovskite solar cells","authors":"Weilin Zhang , Chen Duan , Jimin Du , Mengzhen Du , Xiaojun Li , Cong Li , Qiang Guo , Erjun Zhou","doi":"10.1016/j.dyepig.2024.112516","DOIUrl":"10.1016/j.dyepig.2024.112516","url":null,"abstract":"<div><div>The design and synthesis of hole-transport materials (HTMs) is a hot research topic in perovskite solar cells (PSCs) community. Thanks to the continuous optimization of polymer structures, dopant-free polymers as HTMs have achieved rapid development in PSCs over the past few years. In this study, two D-A type polymers, <strong>PBQ6</strong> and <strong>PBQ9</strong>, are selected as HTMs for CsPbI<sub>2</sub>Br all-inorganic PSCs. Both polymers have the same donor (D) unit of benzodithiophene (BDT) with fluorinated thiophene side chain, but different acceptor (A) unit, fluorinated thiophene for <strong>PBQ6</strong> while chlorinated thiophene for <strong>PBQ9</strong>. Then, the impact of different halogen substitutions on the optical and electrical properties of the polymer HTMs and the photovoltaic performance are investigated. Compared to <strong>PBQ6</strong>, <strong>PBQ9</strong> demonstrates better energy level alignment with CsPbI<sub>2</sub>Br, more efficient carrier extraction and transportation, and enhanced suppression of non-radiative losses. Consequently, CsPbI<sub>2</sub>Br PSCs based on <strong>PBQ9</strong>-HTM achieve a higher power conversion efficiency (PCE) of 16.41 % compared to those based on <strong>PBQ6</strong>-HTM, which exhibit a PCE of 14.93 %. This study underscores the rational side chain engineering on A unit for D-A type polymer can improve the performance of HTMs, thereby further enhancing the efficiency of PSCs.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112516"},"PeriodicalIF":4.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142560780","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}
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