Pub Date : 2025-01-03DOI: 10.1016/j.dyepig.2025.112633
Jiamin Qu , Jianbing Shi , Bin Tong , Zhengxu Cai , Junge Zhi , Yuping Dong
Pyrrole is one of the most common five-membered heterocycles, and its units can be found in many natural products (such as chlorophyll and vitamin B12) and biologically active drugs (e.g., atorvastatin and calcimycin). Owing to their electron-rich properties and multiple modifiable sites, pyrrole derivatives have been widely developed and used in various fields, including medicine and optoelectronic materials. For more than 10 years, we have been working on the development of multi-aryl pyrroles (MAPs) considering the characteristics of aggregation-induced emission (AIE) for biological diagnostic applications. Herein, the structural design of MAPs and their corresponding AIE properties were briefly introduced. Then, MAPs that emit across the full spectrum from ultraviolet–visible to near-infrared II wavelengths were summarized for their application in analyzing and detecting biological substances, bioimaging, and phototherapy. Finally, we demonstrate the potential of MAPs in advancing biomedicine, clinical diagnosis, and cancer treatment.
{"title":"Multi-aryl pyrroles: Exploring aggregation-induced emission for the biological/medical applications","authors":"Jiamin Qu , Jianbing Shi , Bin Tong , Zhengxu Cai , Junge Zhi , Yuping Dong","doi":"10.1016/j.dyepig.2025.112633","DOIUrl":"10.1016/j.dyepig.2025.112633","url":null,"abstract":"<div><div>Pyrrole is one of the most common five-membered heterocycles, and its units can be found in many natural products (such as chlorophyll and vitamin B12) and biologically active drugs (e.g., atorvastatin and calcimycin). Owing to their electron-rich properties and multiple modifiable sites, pyrrole derivatives have been widely developed and used in various fields, including medicine and optoelectronic materials. For more than 10 years, we have been working on the development of multi-aryl pyrroles (MAPs) considering the characteristics of aggregation-induced emission (AIE) for biological diagnostic applications. Herein, the structural design of MAPs and their corresponding AIE properties were briefly introduced. Then, MAPs that emit across the full spectrum from ultraviolet–visible to near-infrared II wavelengths were summarized for their application in analyzing and detecting biological substances, bioimaging, and phototherapy. Finally, we demonstrate the potential of MAPs in advancing biomedicine, clinical diagnosis, and cancer treatment.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112633"},"PeriodicalIF":4.1,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135216","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 : 2025-01-03DOI: 10.1016/j.dyepig.2025.112631
Chao Xu , Nan Ye , Xiaoliang Gou , Leining Feng , Peng Liu , Qingqing Han , Zhegang Huang , Yi-Rong Pei , Long Yi Jin
New types of supramolecular light-responsive assembly systems have been constructed upon the addition of pyrene functional groups to spiropyran-derived amphiphilic rod-coil molecules. These molecules are composed of hydrophobic pyrene, biphenylacetylene and aldehyde-modified spiropyran group as rod building block as well as flexible oligoether chains with non lateral methyl or lateral methyl as coil segment. Our self-assembly investigations revealed that compared to molecules with noncovalently linked pyrene groups, these molecules were arranged relatively compactly during their aggregation via the strong π-π stacking effect provided by the pyrene groups. Meanwhile, we found that the steric hindrance effect of the methyl side chains at the rigid-flexible interface loosely stack the molecules to form nanostructures with a larger curvature in 99 % aqueous solution. Notably, the strong π-π stacking intermolecular interaction of the pyrene and ring-opening isomer induce the formation of nano-assemblies under stimulation with ultraviolet (UV) light, which subsequently block the ring-closing process of the spiropyran in solution, resulting in the construction of new organized disc-like structures and spherical micelles. Interestingly, the solution of complexes formed between rod-coil molecules with pyrene group and 2, 4, 5, 7-tetranitro-9-fluorenone (TNF) displayed good fluorescence sensing performance for TNF in both an organic solvent and mixed solvent system with a high-water content, which has the potential to be developed into sensors suitable for multi-nitro electron acceptor molecules.
{"title":"Controllable isomerization of a light-sensitive spiropyran unit via the assembly of pyrenyl-modified rod-coil amphiphiles","authors":"Chao Xu , Nan Ye , Xiaoliang Gou , Leining Feng , Peng Liu , Qingqing Han , Zhegang Huang , Yi-Rong Pei , Long Yi Jin","doi":"10.1016/j.dyepig.2025.112631","DOIUrl":"10.1016/j.dyepig.2025.112631","url":null,"abstract":"<div><div>New types of supramolecular light-responsive assembly systems have been constructed upon the addition of pyrene functional groups to spiropyran-derived amphiphilic rod-coil molecules. These molecules are composed of hydrophobic pyrene, biphenylacetylene and aldehyde-modified spiropyran group as rod building block as well as flexible oligoether chains with non lateral methyl or lateral methyl as coil segment. Our self-assembly investigations revealed that compared to molecules with noncovalently linked pyrene groups, these molecules were arranged relatively compactly during their aggregation via the strong π-π stacking effect provided by the pyrene groups. Meanwhile, we found that the steric hindrance effect of the methyl side chains at the rigid-flexible interface loosely stack the molecules to form nanostructures with a larger curvature in 99 % aqueous solution. Notably, the strong π-π stacking intermolecular interaction of the pyrene and ring-opening isomer induce the formation of nano-assemblies under stimulation with ultraviolet (UV) light, which subsequently block the ring-closing process of the spiropyran in solution, resulting in the construction of new organized disc-like structures and spherical micelles. Interestingly, the solution of complexes formed between rod-coil molecules with pyrene group and 2, 4, 5, 7-tetranitro-9-fluorenone (TNF) displayed good fluorescence sensing performance for TNF in both an organic solvent and mixed solvent system with a high-water content, which has the potential to be developed into sensors suitable for multi-nitro electron acceptor molecules.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112631"},"PeriodicalIF":4.1,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135028","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 : 2025-01-03DOI: 10.1016/j.dyepig.2024.112626
Adewale O. Adeloye , Simplice Koudjina , Vipin Kumar , Kgaugelo C. Tapala , Joachim D. Gbenou , Prabhakar Chetti
In our search for excellent photoactive materials for optolectronic applications such as dye-sensitized solar cells, four highly emissive, new fluorescent ruthenium coordinated dye complexes (A-D) having pyridyl-3,5-dicarboxylic acid and triphenylphosphine as the two common monodentate ligands formulated as RuCl2(PPh3)2(dca)2, RuCl2(PPh3)Bpy(dca), RuCl2(PPh3)Hbpy(dca) and RuCl2(PPh3)Phen(dca) were prepared in a one-pot synthetic method, purified and characterized by IR, UV–Vis, PL, 1H, 13C, 31P- NMR spectroscopy, elemental analysis, electrochemistry and mass spectrometry. The UV–Vis absorption spectra revealed three to four well-define absorption peaks in the region λmax 265–560 nm which were assigned to the π–π∗ transitions, two ligand-to-ligand charge-transfer (LLCT) bands and dπ(Ru)–π∗(L) transitions respectively. High intensity and broad emissive photoluminescent properties in the mid-infrared region λem (>640 nm) were recorded for all complexes. The electron-donating and/or electron-withdrawing ability of the carboxylic acid and chloride groups present in the complexes possibly favoured a one-electron oxidation reaction, stability of Ru3+/Ru2+ redox properties and the potential of their applications in dye-sensitized solar cells and/or optoelectronics. The calculated results suggest that the frontiers Molecular Orbitals (FMOs), open-circuit voltage (), light-harvesting efficiency (), driving force for electron injection (), dye driving force regeneration (), molecular electrostatic potential (MESP), and density of states () are affected by substituents groups introduced in the ruthenium complex. The of all the dyes are theoretically calculated at JSC 9, 12, and 15 mA cm−2 to give the higher power conversion efficiency () of the solar cell obtained for dye B at (9.36 %). The comparative investigation shows that extended π-spacer variation in the ligands is essential in the fine-tuning of the overall performance of the DSSCs in the ruthenium complexes.
{"title":"One-pot synthesis, photophysical, electrochemical and molecular property of mixed-ligands ruthenium complex functionalities: Potential materials for dye-sensitized solar cells (DSSCs)","authors":"Adewale O. Adeloye , Simplice Koudjina , Vipin Kumar , Kgaugelo C. Tapala , Joachim D. Gbenou , Prabhakar Chetti","doi":"10.1016/j.dyepig.2024.112626","DOIUrl":"10.1016/j.dyepig.2024.112626","url":null,"abstract":"<div><div>In our search for excellent photoactive materials for optolectronic applications such as dye-sensitized solar cells, four highly emissive, new fluorescent ruthenium coordinated dye complexes (<strong>A-D</strong>) having pyridyl-3,5-dicarboxylic acid and triphenylphosphine as the two common monodentate ligands formulated as RuCl<sub>2</sub>(PPh<sub>3</sub>)<sub>2</sub>(dca)<sub>2</sub>, RuCl<sub>2</sub>(PPh<sub>3</sub>)Bpy(dca), RuCl<sub>2</sub>(PPh<sub>3</sub>)Hbpy(dca) and RuCl<sub>2</sub>(PPh<sub>3</sub>)Phen(dca) were prepared in a one-pot synthetic method, purified and characterized by IR, UV–Vis, PL, <sup>1</sup>H, <sup>13</sup>C, <sup>31</sup>P- NMR spectroscopy, elemental analysis, electrochemistry and mass spectrometry. The UV–Vis absorption spectra revealed three to four well-define absorption peaks in the region λ<sub>max</sub> 265–560 nm which were assigned to the π–π∗ transitions, two ligand-to-ligand charge-transfer (LLCT) bands and dπ(Ru)–π∗(L) transitions respectively. High intensity and broad emissive photoluminescent properties in the mid-infrared region λ<sub>em</sub> (>640 nm) were recorded for all complexes. The electron-donating and/or electron-withdrawing ability of the carboxylic acid and chloride groups present in the complexes possibly favoured a one-electron oxidation reaction, stability of Ru<sup>3+</sup>/Ru<sup>2+</sup> redox properties and the potential of their applications in dye-sensitized solar cells and/or optoelectronics. The calculated results suggest that the frontiers Molecular Orbitals (FMOs), open-circuit voltage (<span><math><mrow><msub><mi>V</mi><mtext>oc</mtext></msub></mrow></math></span>), light-harvesting efficiency (<span><math><mrow><mtext>LHE</mtext></mrow></math></span>), driving force for electron injection (<span><math><mrow><mo>Δ</mo><msub><mi>G</mi><mrow><mi>i</mi><mi>n</mi><mi>j</mi></mrow></msub></mrow></math></span>), dye driving force regeneration (<span><math><mrow><mo>Δ</mo><msub><mi>G</mi><mrow><mi>r</mi><mi>e</mi><mi>g</mi></mrow></msub></mrow></math></span>), molecular electrostatic potential (MESP), and density of states (<span><math><mrow><mtext>DOS</mtext></mrow></math></span>) are affected by substituents groups introduced in the ruthenium complex. The <span><math><mrow><mi>η</mi></mrow></math></span> of all the dyes are theoretically calculated at <em>J</em><sub><em>SC</em></sub> 9, 12, and 15 mA cm<sup>−2</sup> to give the higher power conversion efficiency (<span><math><mrow><mi>η</mi></mrow></math></span>) of the solar cell obtained for dye <strong>B</strong> at (9.36 %). The comparative investigation shows that extended π-spacer variation in the ligands is essential in the fine-tuning of the overall performance of the DSSCs in the ruthenium complexes.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112626"},"PeriodicalIF":4.1,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135035","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 : 2025-01-02DOI: 10.1016/j.dyepig.2024.112616
Fuli Xie , Xiangyu Li , Zongtao Wang , Mengzhen Du , Mengwei Ji , Jimin Du , Peiqing Cong , Qing Guo , Erjun Zhou
Developing new material systems simultaneously possessing high open-circuit voltage (VOC) and power conversion efficiency (PCE) has consistently been a focal research. Recently, our group successfully obtained a novel A-DA'D-A type shamrock-shaped NFA via utlizing a large conjugated acenaphtho [1,2-b]quinoxaline imide (AQI) unit as central core (A′ unit) and fluorinated 1,1-dicyanomethylene-3-indanone (IC) as end groups, and the final molecule AQI4 exhibited a PCE of 18 % with a VOC of 0.95 V. To further extend the familly of shamrock-shaped NFAs and upgrade their photovoltaic properties, herein, another shamrock-shaped NFA containing non-halogenated end group IC was synthesized and named as AQI1. The reasonable cooperation of AQI and IC could facilitate to obtain an upshifted LUMO energy level, resulting in a decreased energy loss in organic photovoltaics (OPVs). Using the classic p-type polymer PM6 and a benzotriazole-based linear polymer PE4 as donors, both devices can achieve high VOC of 1.06 V and 1.02 V respectively. Finally, PM6:AQI1 and PE4:AQI1 combinations realized PCEs of 11.3 % and 13.7 % respectively, suggesting that benzotriazole-based polymers might be better choice to blend with shamrock-shaped NFAs. These results indicate that shamrock-shaped NFAs with nonhalogenated end groups may be a feasible and potential design strategy to achieve low-cost and high-VOC OPVs.
{"title":"Shamrock-shaped nonfullerene acceptors containing nonhalogenated end groups for high-voltage organic photovoltaics","authors":"Fuli Xie , Xiangyu Li , Zongtao Wang , Mengzhen Du , Mengwei Ji , Jimin Du , Peiqing Cong , Qing Guo , Erjun Zhou","doi":"10.1016/j.dyepig.2024.112616","DOIUrl":"10.1016/j.dyepig.2024.112616","url":null,"abstract":"<div><div>Developing new material systems simultaneously possessing high open-circuit voltage <em>(V</em><sub>OC</sub>) and power conversion efficiency (PCE) has consistently been a focal research. Recently, our group successfully obtained a novel A-DA'D-A type shamrock-shaped NFA via utlizing a large conjugated acenaphtho [1,2-b]quinoxaline imide (AQI) unit as central core (A′ unit) and fluorinated 1,1-dicyanomethylene-3-indanone (IC) as end groups, and the final molecule AQI4 exhibited a PCE of 18 % with a <em>V</em><sub>OC</sub> of 0.95 V. To further extend the familly of shamrock-shaped NFAs and upgrade their photovoltaic properties, herein, another shamrock-shaped NFA containing non-halogenated end group IC was synthesized and named as AQI1. The reasonable cooperation of AQI and IC could facilitate to obtain an upshifted LUMO energy level, resulting in a decreased energy loss in organic photovoltaics (OPVs). Using the classic p-type polymer PM6 and a benzotriazole-based linear polymer PE4 as donors, both devices can achieve high <em>V</em><sub>OC</sub> of 1.06 V and 1.02 V respectively. Finally, PM6:AQI1 and PE4:AQI1 combinations realized PCEs of 11.3 % and 13.7 % respectively, suggesting that benzotriazole-based polymers might be better choice to blend with shamrock-shaped NFAs. These results indicate that shamrock-shaped NFAs with nonhalogenated end groups may be a feasible and potential design strategy to achieve low-cost and high-<em>V</em><sub>OC</sub> OPVs.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112616"},"PeriodicalIF":4.1,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135538","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 : 2025-01-02DOI: 10.1016/j.dyepig.2024.112630
Tianxin Weng , Jie Liu , Lixia Yuan, Xiangtai Wang, Yanna Zhao, Yongfang Zhang, Yushu Wu, Min Liu
Intelligent DNA nanostructures co-loaded with chemotherapy-phototherapy (CTPT) combination drugs offer a promising solution to the challenge of multidrug resistance (MDR) in tumor cells. The interactions of combined drugs with DNA nanostructures may affect their binding characteristics and cytotoxicity. This study employed a pH-responsive DNA tetrahedron (MUC1-TD) for intelligent delivery of single drug and CTPT combination drugs to overcome MDR. The interactions between MUC1-TD and single drug doxorubicin/idarubicin/new methylene blue N (DOX/IDA/NMBN) or combination drugs (NMBN + DOX/IDA) with MUC1-TD at pH 7.4/5.0 were studied using fluorescence spectroscopy and differential scanning calorimetry, and the thermodynamic parameters were obtained. The drug binding strength followed DOX > IDA > NMBN, and for the same drug, the binding strength was higher at pH 7.4 than at pH 5.0. In the ternary system, different addition orders between drugs had different effects on their binding, among which (MUC1-TD + NMBN) + DOX/IDA was more favorable for drug loading. In vitro pH-controlled release results showed that acidic pH and DNase I jointly expedited the release of NMBN/DOX/IDA from MUC1-TD. The drug release rate was negatively correlated with their binding strength, which was more pronounced in the ternary systems. In vitro cytotoxicity experiments displayed that the synergy of NMBN + DOX/IDA combination drugs was enhanced by MUC1-TD loading, especially the combined effect of NMBN + IDA on MCF-7/ADR cells was most pronounced. This study lays a scientific foundation for the combined CTPT therapy of chemotherapeutic drugs DOX/IDA and photosensitizer NMBN based on intelligent DNA nanostructures.
{"title":"Chemotherapy-phototherapy combination drugs co-loaded by a DNA tetrahedron to overcome drug resistance: The influence of different binding properties of doxorubicin and idarubicin and pH response","authors":"Tianxin Weng , Jie Liu , Lixia Yuan, Xiangtai Wang, Yanna Zhao, Yongfang Zhang, Yushu Wu, Min Liu","doi":"10.1016/j.dyepig.2024.112630","DOIUrl":"10.1016/j.dyepig.2024.112630","url":null,"abstract":"<div><div>Intelligent DNA nanostructures co-loaded with chemotherapy-phototherapy (CTPT) combination drugs offer a promising solution to the challenge of multidrug resistance (MDR) in tumor cells. The interactions of combined drugs with DNA nanostructures may affect their binding characteristics and cytotoxicity. This study employed a pH-responsive DNA tetrahedron (MUC1-TD) for intelligent delivery of single drug and CTPT combination drugs to overcome MDR. The interactions between MUC1-TD and single drug doxorubicin/idarubicin/new methylene blue N (DOX/IDA/NMBN) or combination drugs (NMBN + DOX/IDA) with MUC1-TD at pH 7.4/5.0 were studied using fluorescence spectroscopy and differential scanning calorimetry, and the thermodynamic parameters were obtained. The drug binding strength followed DOX > IDA > NMBN, and for the same drug, the binding strength was higher at pH 7.4 than at pH 5.0. In the ternary system, different addition orders between drugs had different effects on their binding, among which (MUC1-TD + NMBN) + DOX/IDA was more favorable for drug loading. <em>In vitro</em> pH-controlled release results showed that acidic pH and DNase I jointly expedited the release of NMBN/DOX/IDA from MUC1-TD. The drug release rate was negatively correlated with their binding strength, which was more pronounced in the ternary systems. <em>In vitro</em> cytotoxicity experiments displayed that the synergy of NMBN + DOX/IDA combination drugs was enhanced by MUC1-TD loading, especially the combined effect of NMBN + IDA on MCF-7/ADR cells was most pronounced. This study lays a scientific foundation for the combined CTPT therapy of chemotherapeutic drugs DOX/IDA and photosensitizer NMBN based on intelligent DNA nanostructures.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112630"},"PeriodicalIF":4.1,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143134937","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}
Hole transport material (HTMs) is a key component for perovskite solar cells (PSCs) to achieve high photovoltaic performance and good long-term stability. In this study, we developed a series of efficient and cost-effective asymmetric small-molecule HTMs with 9-(4-methoxyphenyl)-9H-3,9′-bicarbazole (BCz) as the core unit, termed BCz-DM and BCz-NP. The design of asymmetric molecular chemical structure for these type HTMs raises up the dipole moment, which is beneficial for enhancing the intermolecular push-pull effect and rendering the HTM higher hole mobility. Moreover, combining with the π-conjugation expansion strategy, asymmetric HTM BCz-NP demonstrates compatible energy levels, along with superior hole mobility and conductivity. Consequently, the PSC device employing BCz-NP as HTM yields an impressive efficiency of 23.58 %, while the PCE of the reference device based on Spiro-OMeTAD is merely 22.77 %. Furthermore, BCz-NP based devices exhibit excellent stability, remaining 86 % of its initial PCEs after 1000 h aging test. These findings provided a promising approach for the improvement of photovoltaic performance for PSCs from the perspective of HTM design.
{"title":"Low-cost asymmetric structured hole transport material for perovskite solar cells","authors":"Wenbin Zhang, Ziyang Xia, Mengde Zhai, Chengyang Liu, Yajie Yang, Meng Yan, Ming Cheng, Cheng Chen","doi":"10.1016/j.dyepig.2024.112629","DOIUrl":"10.1016/j.dyepig.2024.112629","url":null,"abstract":"<div><div>Hole transport material (HTMs) is a key component for perovskite solar cells (PSCs) to achieve high photovoltaic performance and good long-term stability. In this study, we developed a series of efficient and cost-effective asymmetric small-molecule HTMs with 9-(4-methoxyphenyl)-9<em>H</em>-3,9′-bicarbazole (BCz) as the core unit, termed <strong>BCz-DM</strong> and <strong>BCz-NP</strong>. The design of asymmetric molecular chemical structure for these type HTMs raises up the dipole moment, which is beneficial for enhancing the intermolecular push-pull effect and rendering the HTM higher hole mobility. Moreover, combining with the π-conjugation expansion strategy, asymmetric HTM <strong>BCz-NP</strong> demonstrates compatible energy levels, along with superior hole mobility and conductivity. Consequently, the PSC device employing <strong>BCz-NP</strong> as HTM yields an impressive efficiency of 23.58 %, while the PCE of the reference device based on Spiro-OMeTAD is merely 22.77 %. Furthermore, <strong>BCz-NP</strong> based devices exhibit excellent stability, remaining 86 % of its initial PCEs after 1000 h aging test. These findings provided a promising approach for the improvement of photovoltaic performance for PSCs from the perspective of HTM design.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112629"},"PeriodicalIF":4.1,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143134935","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 : 2025-01-01DOI: 10.1016/j.dyepig.2024.112628
Qian Li , Xuelong Huang , Tiantian Zhou, Zengrong Li, Yongjun Deng, Chu Liu, Xinru Chen, Ou Zhang, Zirui Li, Yuqi Li, Yan Liu, Zhixiong Cao
Polymer-based photoacoustic imaging (PAI) in the second near-infrared window (NIR-II, 1000–1700 nm) has gained significant attention due to its unique advantages. However, the development of high-performance polymer contrast agents for NIR-II PAI still falls short of clinical needs, largely owing to a limited understanding of structure-property relationships. This study introduces a series of donor-acceptor (D-A) polymers PT-ATQ, PTT-ATQ, and PDTT-ATQ designed with progressively longer conjugated donor (D) units: thiophene (T), thieno[3,2-b]thiophene (TT), and dithieno[3,2-b:2′,3′-d]thiophene (DTT), aiming to understand the effects of conjugation extension in the D unit on PAI performance. Density functional theory (DFT) calculations showed that increasing the conjugation length enhances electron delocalization along the polymer backbone, boosting the conjugation effect and improving molecular coplanarity. Spectroscopic studies confirmed that this extension of conjugation and enhanced coplanarity significantly raised the absorption coefficient of the water-soluble nanoparticles PDTT-ATQ@NPs. Further results indicated that PDTT-ATQ@NPs not only exhibited excellent biocompatibility but also deliver superior in vitro PAI performance when irradiated with a 1064 nm pulsed laser. In vivo experiments in mice demonstrated a substantial increase in photoacoustic signal intensity, particularly in the ear (138.7-fold) and brain vasculature (64.8-fold), enabling the clear visualization of ear microvessels at 50 μm and brain microvessels at 100 μm. This research highlights the importance of conjugation length in the D unit for enhancing the PAI performance of D-A polymer contrast agents, offering crucial insights into the molecular design for future advancements in this field.
{"title":"Enhanced NIR-II photoacoustic imaging performance of donor-acceptor semiconducting polymers enabled by donor conjugation extension","authors":"Qian Li , Xuelong Huang , Tiantian Zhou, Zengrong Li, Yongjun Deng, Chu Liu, Xinru Chen, Ou Zhang, Zirui Li, Yuqi Li, Yan Liu, Zhixiong Cao","doi":"10.1016/j.dyepig.2024.112628","DOIUrl":"10.1016/j.dyepig.2024.112628","url":null,"abstract":"<div><div>Polymer-based photoacoustic imaging (PAI) in the second near-infrared window (NIR-II, 1000–1700 nm) has gained significant attention due to its unique advantages. However, the development of high-performance polymer contrast agents for NIR-II PAI still falls short of clinical needs, largely owing to a limited understanding of structure-property relationships. This study introduces a series of donor-acceptor (D-A) polymers PT-ATQ, PTT-ATQ, and PDTT-ATQ designed with progressively longer conjugated donor (D) units: thiophene (T), thieno[3,2-<em>b</em>]thiophene (TT), and dithieno[3,2-<em>b</em>:2′,3′-<em>d</em>]thiophene (DTT), aiming to understand the effects of conjugation extension in the D unit on PAI performance. Density functional theory (DFT) calculations showed that increasing the conjugation length enhances electron delocalization along the polymer backbone, boosting the conjugation effect and improving molecular coplanarity. Spectroscopic studies confirmed that this extension of conjugation and enhanced coplanarity significantly raised the absorption coefficient of the water-soluble nanoparticles PDTT-ATQ@NPs. Further results indicated that PDTT-ATQ@NPs not only exhibited excellent biocompatibility but also deliver superior <em>in vitro</em> PAI performance when irradiated with a 1064 nm pulsed laser. <em>In vivo</em> experiments in mice demonstrated a substantial increase in photoacoustic signal intensity, particularly in the ear (138.7-fold) and brain vasculature (64.8-fold), enabling the clear visualization of ear microvessels at 50 μm and brain microvessels at 100 μm. This research highlights the importance of conjugation length in the D unit for enhancing the PAI performance of D-A polymer contrast agents, offering crucial insights into the molecular design for future advancements in this field.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112628"},"PeriodicalIF":4.1,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143134939","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 : 2024-12-31DOI: 10.1016/j.dyepig.2024.112627
Hyeryeon Oh , Jin Sil Lee , Panmo Son , Hyeonyeol Ryu , On Beol Kim , Won Il Choi
The tattoo industry has evolved in recent decades with the increasing prevalence of tattooing. However, the development of ink components, specifically pigments with adequate stability and biocompatibility under physiological conditions remains challenging. In this study, to develop safer pigments for tattoo inks, carbon black (CB) was stabilized with different types of Pluronic polymers and characterized in vitro and in vivo. The effects of the polymer templates on the preparation, morphology, and properties of Pluronic-coated carbon black nanoparticles (CB/Plu NPs) were investigated and optimized using various analytical techniques. In particular, CB/Plu NPs with PF127 at a weight ratio of 1:5 exhibited a high coating yield and dispersion stability. CB/Plu NPs with PF127 possessed spherical morphology with uniform sizes of 158 nm and did not cause cytotoxic effects, cellular morphological changes, or oxidative stress in vitro. Intradermally injected CB/Plu NPs maintained an intense black color for 16 weeks without histological changes in the isolated dorsal skin of a rat. These results suggest that aqueous dispersions of CB/Plu NPs can potentially be used as a highly stable and safe black tattoo ink.
{"title":"Highly stable and safe biocompatible black tattoo ink based on Pluronic polymer-coated carbon black nanoparticles","authors":"Hyeryeon Oh , Jin Sil Lee , Panmo Son , Hyeonyeol Ryu , On Beol Kim , Won Il Choi","doi":"10.1016/j.dyepig.2024.112627","DOIUrl":"10.1016/j.dyepig.2024.112627","url":null,"abstract":"<div><div>The tattoo industry has evolved in recent decades with the increasing prevalence of tattooing. However, the development of ink components, specifically pigments with adequate stability and biocompatibility under physiological conditions remains challenging. In this study, to develop safer pigments for tattoo inks, carbon black (CB) was stabilized with different types of Pluronic polymers and characterized <em>in vitro</em> and <em>in vivo</em>. The effects of the polymer templates on the preparation, morphology, and properties of Pluronic-coated carbon black nanoparticles (CB/Plu NPs) were investigated and optimized using various analytical techniques. In particular, CB/Plu NPs with PF127 at a weight ratio of 1:5 exhibited a high coating yield and dispersion stability. CB/Plu NPs with PF127 possessed spherical morphology with uniform sizes of 158 nm and did not cause cytotoxic effects, cellular morphological changes, or oxidative stress <em>in vitro</em>. Intradermally injected CB/Plu NPs maintained an intense black color for 16 weeks without histological changes in the isolated dorsal skin of a rat. These results suggest that aqueous dispersions of CB/Plu NPs can potentially be used as a highly stable and safe black tattoo ink.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112627"},"PeriodicalIF":4.1,"publicationDate":"2024-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135034","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 : 2024-12-30DOI: 10.1016/j.dyepig.2024.112625
Haoqiang Xu, Wenjing Zhao, Junqing Shi, Lei Ji
Designing high-performance organic scintillators has drawn massive attention for taking advantages of organic frameworks in practical applications. Obtaining large-area scintillating screens efficiently is in high demand for developing organic scintillators. Herein, we developed two pure organic scintillating materials bearing heavy halogen atoms using a simple one-step method. Excitingly, ICzTPN-based scintillating imaging screen has achieved various advantages against the other organic counterparts, i.e., radioluminescence in lower-energy region (reddish-orange color emission, 600 nm), large size (15 cm × 15 cm), high light yield (19094 photons MeV−1), and ultrahigh resolution (28.3 lp/mm). This work offers an efficient design and preparation of pure organic scintillating materials, providing large-area screen with performance ranking at the top level among the reported organic scintillating imaging screens.
{"title":"Large-area imaging screen with ultrahigh resolution achieved by pure organic scintillator","authors":"Haoqiang Xu, Wenjing Zhao, Junqing Shi, Lei Ji","doi":"10.1016/j.dyepig.2024.112625","DOIUrl":"10.1016/j.dyepig.2024.112625","url":null,"abstract":"<div><div>Designing high-performance organic scintillators has drawn massive attention for taking advantages of organic frameworks in practical applications. Obtaining large-area scintillating screens efficiently is in high demand for developing organic scintillators. Herein, we developed two pure organic scintillating materials bearing heavy halogen atoms using a simple one-step method. Excitingly, <strong>ICzTPN</strong>-based scintillating imaging screen has achieved various advantages against the other organic counterparts, i.e., radioluminescence in lower-energy region (reddish-orange color emission, 600 nm), large size (15 cm × 15 cm), high light yield (19094 photons MeV<sup>−1</sup>), and ultrahigh resolution (28.3 lp/mm). This work offers an efficient design and preparation of pure organic scintillating materials, providing large-area screen with performance ranking at the top level among the reported organic scintillating imaging screens.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112625"},"PeriodicalIF":4.1,"publicationDate":"2024-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143134938","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 : 2024-12-30DOI: 10.1016/j.dyepig.2024.112614
Hao Zeng , Xin Fan , Xiaojun He , Zhenlin Jiang , Lin Niu , Haikuan Yuan
Polymer dispersants are widely used for the dispersing of organic pigments, and the stability of the pigment suspension significantly influences the practical application. The anchoring groups in polymer dispersants adsorb on the pigment surfaces, which is the key factor on the dispersion and the stability of pigment suspension. In this study, the dispersants with different anchoring groups were synthesized by solution polymerization to investigate the effect of the anchoring groups on the dispersion of Pigment Red 122. The results demonstrated that the dispersants with the pyridine group as the anchoring group exhibited better dispersion stability, compared to those with a phenyl ring, an aminic function, and an alkyl chain as the anchoring groups. In addition, molecular dynamics (MD) simulation was used to reveal the interaction energy between polymer dispersants and Pigment Red 122. The MD simulation results indicated that the interaction energy of the dispersant with a pyridine anchoring group was the maximum at approximately −368.70 kcal/mol, which was consistent with the experiment results.
{"title":"Influence of anchoring group of dispersants on the dispersion performance of Pigment Red 122","authors":"Hao Zeng , Xin Fan , Xiaojun He , Zhenlin Jiang , Lin Niu , Haikuan Yuan","doi":"10.1016/j.dyepig.2024.112614","DOIUrl":"10.1016/j.dyepig.2024.112614","url":null,"abstract":"<div><div>Polymer dispersants are widely used for the dispersing of organic pigments, and the stability of the pigment suspension significantly influences the practical application. The anchoring groups in polymer dispersants adsorb on the pigment surfaces, which is the key factor on the dispersion and the stability of pigment suspension. In this study, the dispersants with different anchoring groups were synthesized by solution polymerization to investigate the effect of the anchoring groups on the dispersion of Pigment Red 122. The results demonstrated that the dispersants with the pyridine group as the anchoring group exhibited better dispersion stability, compared to those with a phenyl ring, an aminic function, and an alkyl chain as the anchoring groups. In addition, molecular dynamics (MD) simulation was used to reveal the interaction energy between polymer dispersants and Pigment Red 122. The MD simulation results indicated that the interaction energy of the dispersant with a pyridine anchoring group was the maximum at approximately −368.70 kcal/mol, which was consistent with the experiment results.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112614"},"PeriodicalIF":4.1,"publicationDate":"2024-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143134933","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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