Dyes and Pigments最新文献

英文中文

Imidazolium salt end-capped arylene diimides for good solubility, low driving voltage and excellent cycling stability in semi-solid hydrogel-state electrochromic devices

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-25 DOI: 10.1016/j.dyepig.2025.112784

Ye Wu, Zhi-hao Cui, Jia-hao Guo, Rui-jie Qin, Hao Zhang, Wei Shen, Cheng-bin Gong, Qian Tang

Arylene diimide derivatives possess good redox activity owing to their rigid planar conjugated structure and strong electron-deficient aromatic nuclei, but poor solubility and high working voltage limit their practical applications in electrochromic field. In this paper, benzene and naphthalene-based arylene diimides end-capped with imidazolium salts, PMDI-M-C4 and NDI-M-C4, were synthesized and used as the electrochromic materials in both solution- and semi-solid hydrogel-state electrochromic devices. The introduction of imidazolium salts greatly improved their solubility in polar solvents including water, methanol, dimethyl sulfoxide, etc. In solution-state electrochromic devices, both of them showed a moderate working voltage, high optical contrasts (>50 %), high coloration efficiencies (>300 cm²/C), fast switching times (<2 s) and good cycling stability. They showed different colored state due to different aromatic cores, and NDI-M-C4 with a larger conjugation degree core of naphthalene exhibited better cycling stability. In semi-solid carboxymethyl cellulose sodium hydrogel-state electrochromic devices, similar colored states were observed whereas the working voltage was markedly reduced. It's noteworthy that semi-solid hydrogel-state electrochromic device based on NDI-M-C4 performed best with the lowest working voltage of −0.8 V, a high optical contrast of 48.3 %, the best cycling stability and satisfactory coloration efficiency. Finally, the applications of the semi-solid hydrogel-state electrochromic devices in various electronic displays were demonstrated, and its design concept and successful exploration have widely promising applications in displays, adaptive camouflage, bionics, and so on.

{"title":"Imidazolium salt end-capped arylene diimides for good solubility, low driving voltage and excellent cycling stability in semi-solid hydrogel-state electrochromic devices","authors":"Ye Wu, Zhi-hao Cui, Jia-hao Guo, Rui-jie Qin, Hao Zhang, Wei Shen, Cheng-bin Gong, Qian Tang","doi":"10.1016/j.dyepig.2025.112784","DOIUrl":"10.1016/j.dyepig.2025.112784","url":null,"abstract":"<div><div>Arylene diimide derivatives possess good redox activity owing to their rigid planar conjugated structure and strong electron-deficient aromatic nuclei, but poor solubility and high working voltage limit their practical applications in electrochromic field. In this paper, benzene and naphthalene-based arylene diimides end-capped with imidazolium salts, <strong>PMDI-<em>M</em>-C4</strong> and <strong>NDI-<em>M</em>-C4</strong>, were synthesized and used as the electrochromic materials in both solution- and semi-solid hydrogel-state electrochromic devices. The introduction of imidazolium salts greatly improved their solubility in polar solvents including water, methanol, dimethyl sulfoxide, etc. In solution-state electrochromic devices, both of them showed a moderate working voltage, high optical contrasts (>50 %), high coloration efficiencies (>300 cm<sup>2</sup>/C), fast switching times (<2 s) and good cycling stability. They showed different colored state due to different aromatic cores, and <strong>NDI-<em>M</em>-C4</strong> with a larger conjugation degree core of naphthalene exhibited better cycling stability. In semi-solid carboxymethyl cellulose sodium hydrogel-state electrochromic devices, similar colored states were observed whereas the working voltage was markedly reduced. It's noteworthy that semi-solid hydrogel-state electrochromic device based on <strong>NDI-<em>M</em>-C4</strong> performed best with the lowest working voltage of −0.8 V, a high optical contrast of 48.3 %, the best cycling stability and satisfactory coloration efficiency. Finally, the applications of the semi-solid hydrogel-state electrochromic devices in various electronic displays were demonstrated, and its design concept and successful exploration have widely promising applications in displays, adaptive camouflage, bionics, and so on.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112784"},"PeriodicalIF":4.1,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143704704","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

Molecular engineering of carbazole and acridine based hole transport materials for perovskite solar cells

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-24 DOI: 10.1016/j.dyepig.2025.112783

Jingjing Zhao, Licheng Liu, Mengde Zhai, Cheng Chen, Haoxin Wang, Ziyang Xia, Yi Tian, Li Guo, Ming Cheng

The development of novel hole transport materials represents a straightforward and innovative approach to enhancing the performance of perovskite solar cells (PSCs). In this paper, three hole transport materials (HTMs), D-CZ, D-ACR and ACR-CZ, are designed and synthesized through molecular engineering. The alteration of π-bridges in the three molecules resulted in changes in energy levels, which in turn affected their performance. The PSCs using carbazole and acridine based asymmetric structured material ACR-CZ as HTM obtain the highest efficiency of 24.2 % under 100 mW cm⁻² AM 1.5G solar illumination.

引用次数: 0

Efficient near-room-temperature synthesis of thiophene-vinyl-flanked diketopyrrolopyrrole dye-based mesopolymers for high-performance organic field-effect transistors

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-24 DOI: 10.1016/j.dyepig.2025.112782

Jinyang Chen , Wenkang Shi , Ruifang Meng , Minfeng Zeng , Yue Zhao , Tingwei Huang , Shiwei Ren

Two thiophene-vinyl-diketopyrrolopyrrole (TVDPP)-dye-based mesopolymers, PTVDPP-TT and PTVDPP-BT, were synthesized under near-room-temperature conditions. These mesopolymers exhibit non-halogenated solution processability, high molecular coplanarity, narrow bandgaps (approx. 1.2 eV), short π-stacking distances (<3.6 Å), and excellent crystallinity. They demonstrate high hole mobilities of 0.83 and 0.93 cm² V⁻¹ s⁻¹, respectively, for optoelectronic applications in field-effect transistors.

引用次数: 0

Design and synthesis of quadrupolar A-D-A photon absorbing molecules: An investigation into their optical and bioimaging properties

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-24 DOI: 10.1016/j.dyepig.2025.112785

Shufan Yang , Konstantinos Bourdakos , Hiroki Cook , Anna Crisford , Ewan Forsyth , Sumeet Mahajan , Mark Bradley

We herein report on the design and synthesis and optical properties of 4 novel chromophores based on a quadrupole acceptor-donor-acceptor system. These quadrupoles were designed using a fluorene core, coupled to thienyl and thienyl acetylene bridges, to either two 3-dicycanovinylindan-1-ones or two 1,3-bis(dicyanomethylidene)-indanes as strong electron-withdrawing moieties. The structure-property relationships were investigated by computational modelling and photophysical studies, with the fluorophores giving red-emission with large Stokes shifts. The bridged alkynyl units, rather than enhancing conjugation, dramatically reduced fluorescence intensities and wavelength of emission. Notably, two-photon absorption studies revealed cross-section values of δ = 1720 and 780 GM for two of the fluorophores. The fluorophores were explored in one-photon and two-photon fluorescence biological imaging, including the staining of chick bones.

引用次数: 0

Tetraphenylethylene based chiral AIEgen for enantioselective detection of chiral acids

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-22 DOI: 10.1016/j.dyepig.2025.112781

Chunxuan Qi , Qingyang Li , Keyue Wei , Weiwei Zhao , Wangyan Zhang , Miao-Miao Chen , Xiuhua Zhang , Hai-Tao Feng

Enantioselective recognition is crucial in pharmaceutical analysis and life sciences but remains a significant challenge. Herein, we constructed two chiral probes named (1R, 2R)-CHDA-2TPE and (1S, 2S)-CHDA-2TPE, which exhibit typical aggregation-induced emission (AIE) properties. The chiral probes show high enantioselectivity to 11 kinds of chiral reagents. Notably, the fluorescence intensity ratio of the probe with l- and d-glutamic acid was up to 88.8. The ¹H NMR titration results suggested that the hydrogen bond is response for the recognition. These findings implied that the synthesized probes are promising candidates for analyzing chiral compounds.

引用次数: 0

Facile fabrication of biocompatible polymeric microspheres using an AIE-active cellulose derivative for cell imaging

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-22 DOI: 10.1016/j.dyepig.2025.112779

Chunping Ma , Jiyin He , Gaoyi Xie , Yuanyuan Han , Fengyuan Lin , Qiankun Guo , Dongdong Cao , Jinpeng Mo , Haijun Ma , Haibo Xie , Zhenguo Chi , Yongcan Jin

Fluorescent polymeric micromaterials have attracted abiding interest in biomedical applications due to their merits of visualization, fast response, and high sensitivity. Herein, we report a facile strategy for the fabrication of biocompatible polymeric microspheres using an aggregation-induced emission (AIE) active cellulose derivative TPE-CDHPM, which was synthesized through an esterification reaction of microcrystalline cellulose (MCC) and a subsequent Biginelli reaction. The chemical structures of TPE-CDHPM were determined by FT-IR and ¹H NMR spectroscopies, displaying a high degree of substitution of TPE (DS_TPE = 0.73). TPE-CDHPM showed extremely weak fluorescence in the mono-dispersed state while emitting intensively at aggregated state. When dispersed in water, TPE-CDHPM could aggregate into microspheres with a size range of 40–200 nm. The TPE-CDHPM microspheres exhibited an ultralow critical micelle concentration (CMC) of 0.006 mg mL⁻¹, good photoluminescence stability, negligible cytotoxicity, and fascinating biocompatibility, allowing its application in cell imaging. This work offers a direction for effectively constructing biocompatible fluorescent polymeric micromaterials for biomedical applications.

{"title":"Facile fabrication of biocompatible polymeric microspheres using an AIE-active cellulose derivative for cell imaging","authors":"Chunping Ma , Jiyin He , Gaoyi Xie , Yuanyuan Han , Fengyuan Lin , Qiankun Guo , Dongdong Cao , Jinpeng Mo , Haijun Ma , Haibo Xie , Zhenguo Chi , Yongcan Jin","doi":"10.1016/j.dyepig.2025.112779","DOIUrl":"10.1016/j.dyepig.2025.112779","url":null,"abstract":"<div><div>Fluorescent polymeric micromaterials have attracted abiding interest in biomedical applications due to their merits of visualization, fast response, and high sensitivity. Herein, we report a facile strategy for the fabrication of biocompatible polymeric microspheres using an aggregation-induced emission (AIE) active cellulose derivative TPE-CDHPM, which was synthesized through an esterification reaction of microcrystalline cellulose (MCC) and a subsequent Biginelli reaction. The chemical structures of TPE-CDHPM were determined by FT-IR and <sup>1</sup>H NMR spectroscopies, displaying a high degree of substitution of TPE (DS<sub>TPE</sub> = 0.73). TPE-CDHPM showed extremely weak fluorescence in the mono-dispersed state while emitting intensively at aggregated state. When dispersed in water, TPE-CDHPM could aggregate into microspheres with a size range of 40–200 nm. The TPE-CDHPM microspheres exhibited an ultralow critical micelle concentration (CMC) of 0.006 mg mL<sup>−1</sup>, good photoluminescence stability, negligible cytotoxicity, and fascinating biocompatibility, allowing its application in cell imaging. This work offers a direction for effectively constructing biocompatible fluorescent polymeric micromaterials for biomedical applications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112779"},"PeriodicalIF":4.1,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143715133","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 highly bright red-light chemiluminescent probe for inflammation imaging

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-22 DOI: 10.1016/j.dyepig.2025.112780

Haijun Ning , Yuxin Yang , Saran Long , Wen Sun , Jianjun Du , Jiangli Fan , Xiaojun Peng

Both red-light chemiluminescence (CL) emission and high CL efficiency are desirable highly favorable for deep-tissue imaging, however, it was usually achieved by transferring the energy from a CL donor to a fluorophore acceptor based on the CL resonance energy transfer (CRET), which is significantly affected by the spectral overlap range and distance between them. Herein, a red-light CL emitter (L-ISN) was synthesized by conjugating the isoindole BODIPY with the phthaloyl hydrazine moiety (a luminol derivative). When the phthaloyl hydrazine moiety was initiated by ¹O₂, the released reaction energy can be transferred to the whole molecule through intramolecular energy transfer, showing an astonishingly improved CL efficiency by 13 times than luminol. Besides, the CL of L-ISN can penetrate tissues thicker than 2.0 cm, and the limit of detection (LOD) was calculated to be about 52.87 nmol L⁻¹ ¹O₂. When L-ISN nanoparticles (NPs) were prepared by using F127 as the surfactant, L-ISN NPs successfully detected intracellular ¹O₂ and distinguished inflammation tissue in vivo. We believe this study will provide a novel idea for the design of red-light CL emission probe with higher brightness in the field of detection ¹O₂.

{"title":"A highly bright red-light chemiluminescent probe for inflammation imaging","authors":"Haijun Ning , Yuxin Yang , Saran Long , Wen Sun , Jianjun Du , Jiangli Fan , Xiaojun Peng","doi":"10.1016/j.dyepig.2025.112780","DOIUrl":"10.1016/j.dyepig.2025.112780","url":null,"abstract":"<div><div>Both red-light chemiluminescence (CL) emission and high CL efficiency are desirable highly favorable for deep-tissue imaging, however, it was usually achieved by transferring the energy from a CL donor to a fluorophore acceptor based on the CL resonance energy transfer (CRET), which is significantly affected by the spectral overlap range and distance between them. Herein, a red-light CL emitter (L-ISN) was synthesized by conjugating the isoindole BODIPY with the phthaloyl hydrazine moiety (a luminol derivative). When the phthaloyl hydrazine moiety was initiated by <sup>1</sup>O<sub>2</sub>, the released reaction energy can be transferred to the whole molecule through intramolecular energy transfer, showing an astonishingly improved CL efficiency by 13 times than luminol. Besides, the CL of L-ISN can penetrate tissues thicker than 2.0 cm, and the limit of detection (LOD) was calculated to be about 52.87 nmol L<sup>−1</sup> <sup>1</sup>O<sub>2</sub>. When L-ISN nanoparticles (NPs) were prepared by using F127 as the surfactant, L-ISN NPs successfully detected intracellular <sup>1</sup>O<sub>2</sub> and distinguished inflammation tissue <em>in vivo</em>. We believe this study will provide a novel idea for the design of red-light CL emission probe with higher brightness in the field of detection <sup>1</sup>O<sub>2</sub>.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112780"},"PeriodicalIF":4.1,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143739198","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

Nitrogen-mediated dyeing of denim with natural indigo: Towards sustainable and efficient coloration

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-22 DOI: 10.1016/j.dyepig.2025.112778

Kangkang Wang, Qingliang Luo, Wei Ding, Qiangqiang Zhang, Dongxiao Ji, Rongwu Wang, Xiaohong Qin

The conventional indigo dyeing process for denim production poses significant environmental challenges. While natural indigo dyes offer eco-friendly alternatives, their application is limited by low dye uptake and poor color fastness. This study integrates molecular dynamics simulations and experimental approaches to explore the effects of nitrogen (N₂) protected dyeing technology on natural indigo performance. Results reveal that N₂ protection enhances the hydrogen bonding in cellulose fibers, strengthens dye-fiber interactions, and improves dye diffusion, leading to superior dyeing outcomes. Using response surface methodology (RSM), we identified N₂ concentration and dyeing temperature as key factors influencing coloration efficiency and fastness. Under optimized conditions, natural indigo achieved performance comparable to synthetic dyes while exhibiting enhanced biodegradability in residual dye baths. Compared to conventional synthetic indigo dyeing processes, the N₂-assisted natural indigo dyeing strategy achieves a 41.45 % reduction in chemical consumption, and 28.72 % decrease in energy consumption and CO₂ emissions. These results validate its dual advantages in enhancing dye utilization efficiency and ecological sustainability. This work provides a theoretical foundation for sustainable denim dyeing and advances eco-conscious practices in textile industry, offering both scientific and practical insights.

{"title":"Nitrogen-mediated dyeing of denim with natural indigo: Towards sustainable and efficient coloration","authors":"Kangkang Wang, Qingliang Luo, Wei Ding, Qiangqiang Zhang, Dongxiao Ji, Rongwu Wang, Xiaohong Qin","doi":"10.1016/j.dyepig.2025.112778","DOIUrl":"10.1016/j.dyepig.2025.112778","url":null,"abstract":"<div><div>The conventional indigo dyeing process for denim production poses significant environmental challenges. While natural indigo dyes offer eco-friendly alternatives, their application is limited by low dye uptake and poor color fastness. This study integrates molecular dynamics simulations and experimental approaches to explore the effects of nitrogen (N<sub>2</sub>) protected dyeing technology on natural indigo performance. Results reveal that N<sub>2</sub> protection enhances the hydrogen bonding in cellulose fibers, strengthens dye-fiber interactions, and improves dye diffusion, leading to superior dyeing outcomes. Using response surface methodology (RSM), we identified N<sub>2</sub> concentration and dyeing temperature as key factors influencing coloration efficiency and fastness. Under optimized conditions, natural indigo achieved performance comparable to synthetic dyes while exhibiting enhanced biodegradability in residual dye baths. Compared to conventional synthetic indigo dyeing processes, the N<sub>2</sub>-assisted natural indigo dyeing strategy achieves a 41.45 % reduction in chemical consumption, and 28.72 % decrease in energy consumption and CO<sub>2</sub> emissions. These results validate its dual advantages in enhancing dye utilization efficiency and ecological sustainability. This work provides a theoretical foundation for sustainable denim dyeing and advances eco-conscious practices in textile industry, offering both scientific and practical insights.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112778"},"PeriodicalIF":4.1,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678410","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

Synthesis and photophysical properties of π-extended carboxyl BODIPYs: An experimental and theoretical study

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-22 DOI: 10.1016/j.dyepig.2025.112776

Gökhan Sevinç , Elif Akhüseyin Yıldız , Zeliha Pınar Taşkıran , Ahmet Karatay

A series of new boron-dipyrromethenes (BODIPYs) bearing 4-carboxyphenyl unit at the meso (8) position of the BODIPY core have been successfully synthesized through the reactions of 2,4-diaryl substituted pyrroles with 4-formylbenzoic acid. The palladium-catalyzed Suzuki-Miyaura coupling reactions were performed on the meso unsubstituted BODIPY derivatives with 4-carboxyphenyl boronic acid to obtain distal and proximal substitution. Chemical structures were characterized using high resolution mass spectrometry (HRMS), ¹H/¹³C NMR, and FTIR spectroscopy. The photophysical properties, excited state dynamics, and thermal degradation profiles were investigated in terms of aromatic subunits using electronic absorption/fluorescence measurements, femtosecond transient absorption spectroscopy, and thermogravimetric analysis (TGA), respectively. Experimentally investigated absorption and fluorescence properties, as well as structural features, were clarified using density functional theory (DFT) and electron-hole analysis. The absorption of the compounds ranges from 504 to 594 nm, and their emission ranges from 609 to 640 nm, depending on the aromatic groups at the BODIPY core. Performed pump probe spectroscopy measurements revealed that the excited state lifetime is shortened for 3,5 (proximal) positions compared to 1,7 (distal) positions due to increasing interactions between the molecular orbitals. The local n–π and π-π∗ excitations from DFT calculations and electron-hole analysis mainly characterize the electronic transitions, leading to limited intramolecular charge transfer to the BODIPY core. Charge transfer is highest at the 3,5-positions, decreases at the meso (8) position, and is lowest at the 1,7-positions of the BODIPY core. The newly developed BODIPYs with carboxyl groups show potential as agents in applications demanding extensive absorption and strong emission characteristics.

{"title":"Synthesis and photophysical properties of π-extended carboxyl BODIPYs: An experimental and theoretical study","authors":"Gökhan Sevinç , Elif Akhüseyin Yıldız , Zeliha Pınar Taşkıran , Ahmet Karatay","doi":"10.1016/j.dyepig.2025.112776","DOIUrl":"10.1016/j.dyepig.2025.112776","url":null,"abstract":"<div><div>A series of new boron-dipyrromethenes (BODIPYs) bearing 4-carboxyphenyl unit at the <em>meso</em> (8) position of the BODIPY core have been successfully synthesized through the reactions of 2,4-diaryl substituted pyrroles with 4-formylbenzoic acid. The palladium-catalyzed Suzuki-Miyaura coupling reactions were performed on the <em>meso</em> unsubstituted BODIPY derivatives with 4-carboxyphenyl boronic acid to obtain distal and proximal substitution. Chemical structures were characterized using high resolution mass spectrometry (HRMS), <sup>1</sup>H/<sup>13</sup>C NMR, and FTIR spectroscopy. The photophysical properties, excited state dynamics, and thermal degradation profiles were investigated in terms of aromatic subunits using electronic absorption/fluorescence measurements, femtosecond transient absorption spectroscopy, and thermogravimetric analysis (TGA), respectively. Experimentally investigated absorption and fluorescence properties, as well as structural features, were clarified using density functional theory (DFT) and electron-hole analysis. The absorption of the compounds ranges from 504 to 594 nm, and their emission ranges from 609 to 640 nm, depending on the aromatic groups at the BODIPY core. Performed pump probe spectroscopy measurements revealed that the excited state lifetime is shortened for 3,5 (proximal) positions compared to 1,7 (distal) positions due to increasing interactions between the molecular orbitals. The local n–π and π-π∗ excitations from DFT calculations and electron-hole analysis mainly characterize the electronic transitions, leading to limited intramolecular charge transfer to the BODIPY core. Charge transfer is highest at the 3,5-positions, decreases at the <em>meso</em> (8) position, and is lowest at the 1,7-positions of the BODIPY core. The newly developed BODIPYs with carboxyl groups show potential as agents in applications demanding extensive absorption and strong emission characteristics.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112776"},"PeriodicalIF":4.1,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678407","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 emitting aza-BODIPY fluorophores, impact of N,N-dialkylamino groups on the photophysical properties: synthesis, characterization, and computational studies

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-22 DOI: 10.1016/j.dyepig.2025.112773

Wassima Tajani , Ludmilla Verrieux , Annika Sickinger , Amélie Godard , Jean Rouillon , Christine Goze , Fabien Dalonneau , Yoann Rousselin , Olivier Maury , Lucie Sancey , Chantal Andraud , Boris Le Guennic , Arnaud Fihey , Ewen Bodio

The development of new fluorophores emitting in the near-infrared (NIR-I and/or NIR-II) region is currently a major focus of research in fields such as optics, energy, and medical imaging. Among these fluorophores, aza-BODIPYs have emerged as a particularly promising family. However, the challenge lies in determining which structural modifications are necessary to achieve the desired photophysical properties. This study aims to elucidate the impact of electron-donating groups, specifically N,N-dialkylamino groups, on these properties, depending on their number and position. A series of 14 aza-BODIPYs, without and with one to four N,N-dimethylamino groups, was synthesized, chemically characterized (NMR, HRMS, X-ray diffraction), and photochemically analyzed. Their photophysical properties were compared, and molecular modeling ((TD)-DFT) was performed to rationalize these properties. Preliminary tests in biological media were also conducted.

{"title":"Near-infrared emitting aza-BODIPY fluorophores, impact of N,N-dialkylamino groups on the photophysical properties: synthesis, characterization, and computational studies","authors":"Wassima Tajani , Ludmilla Verrieux , Annika Sickinger , Amélie Godard , Jean Rouillon , Christine Goze , Fabien Dalonneau , Yoann Rousselin , Olivier Maury , Lucie Sancey , Chantal Andraud , Boris Le Guennic , Arnaud Fihey , Ewen Bodio","doi":"10.1016/j.dyepig.2025.112773","DOIUrl":"10.1016/j.dyepig.2025.112773","url":null,"abstract":"<div><div>The development of new fluorophores emitting in the near-infrared (NIR-I and/or NIR-II) region is currently a major focus of research in fields such as optics, energy, and medical imaging. Among these fluorophores, aza-BODIPYs have emerged as a particularly promising family. However, the challenge lies in determining which structural modifications are necessary to achieve the desired photophysical properties. This study aims to elucidate the impact of electron-donating groups, specifically <em>N</em>,<em>N</em>-dialkylamino groups, on these properties, depending on their number and position. A series of 14 aza-BODIPYs, without and with one to four <em>N</em>,<em>N</em>-dimethylamino groups, was synthesized, chemically characterized (NMR, HRMS, X-ray diffraction), and photochemically analyzed. Their photophysical properties were compared, and molecular modeling ((TD)-DFT) was performed to rationalize these properties. Preliminary tests in biological media were also conducted.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112773"},"PeriodicalIF":4.1,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143807890","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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Dyes and Pigments

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