Dyes and Pigments最新文献

英文中文

Fluorescent properties and bioimaging potential of phenyl-substituted symmetrical furan diketopyrrolopyrroles

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-18 DOI: 10.1016/j.dyepig.2025.112700

Karel Pauk , Monika Hejdová , Aleš Imramovský , Dawid Zych , Sylwia Zimosz , Katarzyna Malarz , Robert Musioł , Aneta Slodek

Three symmetrical D-A-D systems of N-alkylated 3,6-difuran-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione (EHDPP) with various π conjugated aromatic part based on furan moiety were designed, synthesised and fully characterised. These three different π-extended chromophores show different intramolecular charge transfer properties. Photophysical analysis of EHDPP derivatives revealed broad absorption in the 300–620 nm range, shifting absorption maxima by 60 nm with increasing π-conjugation. Emission studies showed intense fluorescence from 520 to 680 nm with 30–79 % quantum yields, which improved with increasing conjugation. The polarity of the solvent had minimal influence on the absorption spectra, but a slight positive solvatochromism was observed in the emission spectra, confirming the stabilised excited states with donor-acceptor characteristics. Low-temperature studies further revealed enhanced vibronic features and extended lifetimes, particularly for EHDPP-PF with 2-phenylfuran units, attributed to suppressing nonradiative processes. DFT analysis of molecular orbitals reveals increasing substituent contributions to HOMO and LUMO orbitals from furan to 2-phenylfuran, correlating with the enhanced donating ability of terminal groups. A preliminary biological study highlighted the potential of these derivatives as fluorescent cellular probes. The compounds exhibited strong fluorescence stability and negligible cytotoxicity at concentrations suitable for staining cellular compartments, making them promising candidates for biological imaging applications. These findings highlight the importance of terminal substituent modification in tuning the photophysical and electronic properties of EHDPP derivatives.

{"title":"Fluorescent properties and bioimaging potential of phenyl-substituted symmetrical furan diketopyrrolopyrroles","authors":"Karel Pauk , Monika Hejdová , Aleš Imramovský , Dawid Zych , Sylwia Zimosz , Katarzyna Malarz , Robert Musioł , Aneta Slodek","doi":"10.1016/j.dyepig.2025.112700","DOIUrl":"10.1016/j.dyepig.2025.112700","url":null,"abstract":"<div><div>Three symmetrical D-A-D systems of <em>N</em>-alkylated 3,6-difuran-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione (<strong>EHDPP</strong>) with various π conjugated aromatic part based on furan moiety were designed, synthesised and fully characterised. These three different π-extended chromophores show different intramolecular charge transfer properties. Photophysical analysis of <strong>EHDPP</strong> derivatives revealed broad absorption in the 300–620 nm range, shifting absorption maxima by 60 nm with increasing π-conjugation. Emission studies showed intense fluorescence from 520 to 680 nm with 30–79 % quantum yields, which improved with increasing conjugation. The polarity of the solvent had minimal influence on the absorption spectra, but a slight positive solvatochromism was observed in the emission spectra, confirming the stabilised excited states with donor-acceptor characteristics. Low-temperature studies further revealed enhanced vibronic features and extended lifetimes, particularly for <strong>EHDPP-PF</strong> with 2-phenylfuran units, attributed to suppressing nonradiative processes. DFT analysis of molecular orbitals reveals increasing substituent contributions to HOMO and LUMO orbitals from furan to 2-phenylfuran, correlating with the enhanced donating ability of terminal groups. A preliminary biological study highlighted the potential of these derivatives as fluorescent cellular probes. The compounds exhibited strong fluorescence stability and negligible cytotoxicity at concentrations suitable for staining cellular compartments, making them promising candidates for biological imaging applications. These findings highlight the importance of terminal substituent modification in tuning the photophysical and electronic properties of <strong>EHDPP</strong> derivatives.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"238 ","pages":"Article 112700"},"PeriodicalIF":4.1,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143471412","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

Thermally converted anthracene-based fully conjugated polymers for field-effect transistors via molecular doping

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-17 DOI: 10.1016/j.dyepig.2025.112709

Zhihao Meng , Tianyang Wang , Junxuan Tu , Zhenglin Han , Yuxuan Deng , Chunfeng Shi , Lei Zhang , Yonggang Zhen

Anthracenes have become one of most important organic semiconducting materials owing to the high stability and superior mobility. However, anthracene-based polymers lag far behind small-molecule counterparts in the light of material quantity and carrier mobility. Generally, solubilizing groups such as alkyl chains need to be introduced to conjugated polymer backbone for solution processability, which reduce the density of π electrons and sterically disturb the π stacking, hence degrading charge transport performance. Herein, we synthesize a series of anthracene-based fully conjugated polymers by thermal conversion via retro-Diels-Alder reaction, which were confirmed by thermogravimetric analysis, FT-IR, and UV–vis absorption spectroscopy. The anthracene-based polymers can resist effectively organic common solvents without affecting electrical properties. Furthermore, oriented fibrous thin film can be achieved by doping of electron acceptors such as 1,2,4,5-tetracyanobenzene (TCNB) and 7,7,8,8-tetracyanoquinodimethane (TCNQ), showing 4–5 times increased carrier mobilities relative to pristine films.

{"title":"Thermally converted anthracene-based fully conjugated polymers for field-effect transistors via molecular doping","authors":"Zhihao Meng , Tianyang Wang , Junxuan Tu , Zhenglin Han , Yuxuan Deng , Chunfeng Shi , Lei Zhang , Yonggang Zhen","doi":"10.1016/j.dyepig.2025.112709","DOIUrl":"10.1016/j.dyepig.2025.112709","url":null,"abstract":"<div><div>Anthracenes have become one of most important organic semiconducting materials owing to the high stability and superior mobility. However, anthracene-based polymers lag far behind small-molecule counterparts in the light of material quantity and carrier mobility. Generally, solubilizing groups such as alkyl chains need to be introduced to conjugated polymer backbone for solution processability, which reduce the density of π electrons and sterically disturb the π stacking, hence degrading charge transport performance. Herein, we synthesize a series of anthracene-based fully conjugated polymers by thermal conversion via retro-Diels-Alder reaction, which were confirmed by thermogravimetric analysis, FT-IR, and UV–vis absorption spectroscopy. The anthracene-based polymers can resist effectively organic common solvents without affecting electrical properties. Furthermore, oriented fibrous thin film can be achieved by doping of electron acceptors such as 1,2,4,5-tetracyanobenzene (TCNB) and 7,7,8,8-tetracyanoquinodimethane (TCNQ), showing 4–5 times increased carrier mobilities relative to pristine films.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"238 ","pages":"Article 112709"},"PeriodicalIF":4.1,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143471411","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

Optimizing bicontinuous network morphology by precisely regulating alkyl sulfur group side-chain for organic solar cells

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-17 DOI: 10.1016/j.dyepig.2025.112713

Junhong Liang , Xudong Li , Furong Shi , Jinye He , Sheng Guan , Yuan Zhou , Pengzhi Guo , Chenglong Wang , Yangjun Xia

Continuous interpenetrating network morphology on the performance of organic solar cells (OSCs) have the effect of ease, how to control the bulk heterojunction (BHJ) the formation of the fiber morphology is of vital importance. In this study, a series of polymers were synthesized by rationally varying the atoms connecting the conjugated backbone and side chains, PBDT-T-SBDD, PBDT-TS-SBDD and PBDT-TDS-SBDD were used to systematically study the effects of sulfur atom on the electron conformation of the molecule, the morphology of the blend film and the properties of the device. We found that the introduction of sulfur atoms can enhance the intermolecular interaction, thus reducing the energy disorder of the blend film. However, excessive introduction of sulfur atoms leads to excessive steric hindrance of side chain of the molecules, resulting in excessive local aggregation. Compared with PBDT-T-SBDD: Y6 and PBDT-TDS-SBDD: Y6-based OSCs, PBDT-TS-SBDD: Y6-based OSCs has both higher photovoltaic performance, reaching a PCE of 11.33 %, due to the well-defined fiber structure which significantly improves the charge transport channel and phase separation of the blend film.

{"title":"Optimizing bicontinuous network morphology by precisely regulating alkyl sulfur group side-chain for organic solar cells","authors":"Junhong Liang , Xudong Li , Furong Shi , Jinye He , Sheng Guan , Yuan Zhou , Pengzhi Guo , Chenglong Wang , Yangjun Xia","doi":"10.1016/j.dyepig.2025.112713","DOIUrl":"10.1016/j.dyepig.2025.112713","url":null,"abstract":"<div><div>Continuous interpenetrating network morphology on the performance of organic solar cells (OSCs) have the effect of ease, how to control the bulk heterojunction (BHJ) the formation of the fiber morphology is of vital importance. In this study, a series of polymers were synthesized by rationally varying the atoms connecting the conjugated backbone and side chains, PBDT-T-SBDD, PBDT-TS-SBDD and PBDT-TDS-SBDD were used to systematically study the effects of sulfur atom on the electron conformation of the molecule, the morphology of the blend film and the properties of the device. We found that the introduction of sulfur atoms can enhance the intermolecular interaction, thus reducing the energy disorder of the blend film. However, excessive introduction of sulfur atoms leads to excessive steric hindrance of side chain of the molecules, resulting in excessive local aggregation. Compared with PBDT-T-SBDD: Y6 and PBDT-TDS-SBDD: Y6-based OSCs, PBDT-TS-SBDD: Y6-based OSCs has both higher photovoltaic performance, reaching a PCE of 11.33 %, due to the well-defined fiber structure which significantly improves the charge transport channel and phase separation of the blend film.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"237 ","pages":"Article 112713"},"PeriodicalIF":4.1,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143444411","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

Glutathione and tyrosinase Co-activated near-infrared fluorescent probes for precise detection of melanoma

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-16 DOI: 10.1016/j.dyepig.2025.112712

Dan Wu , Chao Gan , Chao He , Yan Wu , Peng-Yu Ji , Cheng Xing , Li-Qiong Yao

Melanoma is a highly aggressive malignant tumor, and precise diagnosis is essential but remains to be explored. Making full use of the widespread correlation biomarker in melanoma to develop the dual-locked NIR fluorescence probe is of great importance for the accurate diagnosis and treatment of melanoma. Herein, we proposed a novel dual-locked NIR fluorescent probe Cy-Dual by utilizing two interrelated characteristic biomarkers of melanoma. Cy-Dual remained fluorescent off in normal cells, yet turn on remarkable NIR fluorescence after the co-activation of two melanoma-associated markers, namely, glutathione and tyrosinase. In-depth cell bioimaging results indicate that Cy-Dual allows highly specific imaging of melanoma cells, making it a powerful tool for accurately detecting melanomas. More impressively, such co-activated probe further enables the real-time imaging diagnosis of melanoma in vivo utilizing a xenograft tumor-bearing mice model. This study provides a non-invasive imaging technique for melanoma, which facilitates advancements in precision medicine related to melanoma.

{"title":"Glutathione and tyrosinase Co-activated near-infrared fluorescent probes for precise detection of melanoma","authors":"Dan Wu , Chao Gan , Chao He , Yan Wu , Peng-Yu Ji , Cheng Xing , Li-Qiong Yao","doi":"10.1016/j.dyepig.2025.112712","DOIUrl":"10.1016/j.dyepig.2025.112712","url":null,"abstract":"<div><div>Melanoma is a highly aggressive malignant tumor, and precise diagnosis is essential but remains to be explored. Making full use of the widespread correlation biomarker in melanoma to develop the dual-locked NIR fluorescence probe is of great importance for the accurate diagnosis and treatment of melanoma. Herein, we proposed a novel dual-locked NIR fluorescent probe Cy-Dual by utilizing two interrelated characteristic biomarkers of melanoma. Cy-Dual remained fluorescent off in normal cells, yet turn on remarkable NIR fluorescence after the co-activation of two melanoma-associated markers, namely, glutathione and tyrosinase. In-depth cell bioimaging results indicate that Cy-Dual allows highly specific imaging of melanoma cells, making it a powerful tool for accurately detecting melanomas. More impressively, such co-activated probe further enables the real-time imaging diagnosis of melanoma <em>in vivo</em> utilizing a xenograft tumor-bearing mice model. This study provides a non-invasive imaging technique for melanoma, which facilitates advancements in precision medicine related to melanoma.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"237 ","pages":"Article 112712"},"PeriodicalIF":4.1,"publicationDate":"2025-02-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143444310","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

Recent advances in Schiff base coinage metal complexes as anticancer agents: A comprehensive review (2021–2025) 希夫碱共价金属配合物作为抗癌剂的最新进展：全面综述（2021-2025）

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-15 DOI: 10.1016/j.dyepig.2025.112710

Mohammed Fareed Felemban , Faris J. Tayeb , Ali Alqarni , Dr Amal Adnan Ashour , Dr Alaa Shafie

Cancer remains one of the most critical global health challenges, accounting for a substantial number of deaths worldwide. Conventional anticancer therapies, such as chemotherapy and radiation, are often accompanied by severe side effects, drug resistance, and limited specificity in targeting cancer cells, necessitating the development of novel, effective, and targeted therapeutic agents. Among the various strategies explored, metal-based drugs have attracted significant attention due to their unique chemical and biological properties. Schiff base compounds, with their versatile structural frameworks, have emerged as promising candidates in medicinal chemistry, owing to their ability to chelate metal ions and exhibit potent anticancer activities. In particular, Schiff base complexes with coinage metals (Cu, Ag and Au) have gained significant interest due to their unique redox properties, strong DNA-binding capabilities, and the ability to generate reactive oxygen species (ROS), which induce apoptosis in cancer cells. The aim of this review is to provide a comprehensive analysis of Schiff base coinage metal complexes, as potential anticancer agents. The review explores how the structural attributes of Schiff base ligands influence the biological activities of these complexes. Furthermore, recent advancements (2021–2025) in the development of these complexes are discussed, highlighting their efficacy against various cancer types and the specific advantages of incorporating coinage metals into Schiff base frameworks.

{"title":"Recent advances in Schiff base coinage metal complexes as anticancer agents: A comprehensive review (2021–2025)","authors":"Mohammed Fareed Felemban , Faris J. Tayeb , Ali Alqarni , Dr Amal Adnan Ashour , Dr Alaa Shafie","doi":"10.1016/j.dyepig.2025.112710","DOIUrl":"10.1016/j.dyepig.2025.112710","url":null,"abstract":"<div><div>Cancer remains one of the most critical global health challenges, accounting for a substantial number of deaths worldwide. Conventional anticancer therapies, such as chemotherapy and radiation, are often accompanied by severe side effects, drug resistance, and limited specificity in targeting cancer cells, necessitating the development of novel, effective, and targeted therapeutic agents. Among the various strategies explored, metal-based drugs have attracted significant attention due to their unique chemical and biological properties. Schiff base compounds, with their versatile structural frameworks, have emerged as promising candidates in medicinal chemistry, owing to their ability to chelate metal ions and exhibit potent anticancer activities. In particular, Schiff base complexes with coinage metals (Cu, Ag and Au) have gained significant interest due to their unique redox properties, strong DNA-binding capabilities, and the ability to generate reactive oxygen species (ROS), which induce apoptosis in cancer cells. The aim of this review is to provide a comprehensive analysis of Schiff base coinage metal complexes, as potential anticancer agents. The review explores how the structural attributes of Schiff base ligands influence the biological activities of these complexes. Furthermore, recent advancements (2021–2025) in the development of these complexes are discussed, highlighting their efficacy against various cancer types and the specific advantages of incorporating coinage metals into Schiff base frameworks.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"237 ","pages":"Article 112710"},"PeriodicalIF":4.1,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143429803","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

The amazing world of biological pigments: A review on microbial melanins

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-15 DOI: 10.1016/j.dyepig.2025.112711

Divya Singh , Deepshikha , Venkatesh Chaturvedi , Pradeep Verma

Biological pigments fundamentally fall into two main categories: photosynthetic pigments and photoprotective pigments. Photosynthetic pigments are essential for photosynthesis whereas photoprotective pigments are necessary for protection against harmful solar radiations including UV-B rays. Among all the photoprotective pigments, melanin is considered to be the key player as it is synthesized in a variety of living organisms. In nature, melanin acts as a photo protectant, chelating agent, antioxidant, charge transport mediator, metal ion balancer and a critical camouflaging colorant. The biosynthesis of melanin involves the enzymes tyrosinase, laccase, and 4-hydroxyphenylpyruvate dioxygenase respectively, that employ different substrates to form a variety of melanin's. The production and extraction of these polymers from plants and animals is a challenging task. Therefore, the focus has shifted to inexpensive sources such as microbes. Also, with the help of recombinant DNA technology, it is possible to increase melanin production. In this review, we have discussed different types of pigment occurring in plants, animals and microbes with special reference to melanin. We have also emphasized on the pathways involved in synthesis of major classes of melanin. Finally, the latest advances towards strain improvement and process development methods along with biological functions, and applications of melanin are also summarized and discussed.

生物色素主要分为两大类：光合色素和光保护色素。光合色素是进行光合作用所必需的，而光保护色素则是抵御包括紫外线-B 在内的有害太阳辐射所必需的。在所有光保护色素中，黑色素被认为是最重要的色素，因为它可以在各种生物体内合成。在自然界中，黑色素是一种光保护剂、螯合剂、抗氧化剂、电荷传输介质、金属离子平衡剂和重要的伪装着色剂。黑色素的生物合成涉及酪氨酸酶、漆酶和 4-羟基苯基丙酮酸二氧酶，它们分别利用不同的底物形成各种黑色素。从动植物中生产和提取这些聚合物是一项具有挑战性的任务。因此，研究重点已转向微生物等廉价来源。此外，在 DNA 重组技术的帮助下，提高黑色素产量也成为可能。在这篇综述中，我们讨论了植物、动物和微生物中存在的不同类型的色素，并特别提到了黑色素。我们还强调了合成主要类别黑色素的途径。最后，我们还总结并讨论了菌种改良和工艺开发方法的最新进展，以及黑色素的生物功能和应用。

{"title":"The amazing world of biological pigments: A review on microbial melanins","authors":"Divya Singh , Deepshikha , Venkatesh Chaturvedi , Pradeep Verma","doi":"10.1016/j.dyepig.2025.112711","DOIUrl":"10.1016/j.dyepig.2025.112711","url":null,"abstract":"<div><div>Biological pigments fundamentally fall into two main categories: photosynthetic pigments and photoprotective pigments. Photosynthetic pigments are essential for photosynthesis whereas photoprotective pigments are necessary for protection against harmful solar radiations including UV-B rays. Among all the photoprotective pigments, melanin is considered to be the key player as it is synthesized in a variety of living organisms. In nature, melanin acts as a photo protectant, chelating agent, antioxidant, charge transport mediator, metal ion balancer and a critical camouflaging colorant. The biosynthesis of melanin involves the enzymes tyrosinase, laccase, and 4-hydroxyphenylpyruvate dioxygenase respectively, that employ different substrates to form a variety of melanin's. The production and extraction of these polymers from plants and animals is a challenging task. Therefore, the focus has shifted to inexpensive sources such as microbes. Also, with the help of recombinant DNA technology, it is possible to increase melanin production. In this review, we have discussed different types of pigment occurring in plants, animals and microbes with special reference to melanin. We have also emphasized on the pathways involved in synthesis of major classes of melanin. Finally, the latest advances towards strain improvement and process development methods along with biological functions, and applications of melanin are also summarized and discussed.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"237 ","pages":"Article 112711"},"PeriodicalIF":4.1,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143438270","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

In-silico color prediction process for natural dyes in Madder

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-14 DOI: 10.1016/j.dyepig.2025.112701

Thanh Huyen Linh Tran , Romain Berraud-Pache , Maguy Jaber

In the field of cultural heritage, accurately identifying the colors produced by madder root dyes without alteration is critical. In fact, textile dyeing using extracts from their roots has been performed for centuries. Many examples of madder dye remain today in museum and conservation collections. Madder is an interesting natural source of dye because it contains up to 68 different colorants. However, many of these dyes are extremely sensitive to hydrolysis, decarboxylation, and degradation from enzymes, extraction chemicals, and processing temperatures. The valuable chemical information embedded in the dye structure may be lost if extraction and analysis are too harsh, resulting in inaccurate color prediction with large color differences. Thus, they are often overlooked as colorants in historical textiles. Over the past decades, traditional extraction techniques have been used to analyze textiles but they are invasive and destructive. As a result, this method is expensive, time-consuming, and in some cases is not suited for the analysis of artwork. But in the last decades, computer techniques have been presented as a powerful tool that enables the prediction of UV–VIS signature spectra and color coordinates with high accuracy using Time-Dependent Density Functional Theory. The aim of this study is to elaborate an efficient color prediction process of madder's root without any chemical degradation of dyes. It will enable the creation of a robust analytical database to identify madder colors in heritage objects. Here, we provide a rapid method to obtain a complete database of predicted UV–VIS spectra and color of anthraquinone derivatives found in Madder. In the context of historical textiles, the detailed color of natural colorants present in the artwork is of paramount importance for conservation and restoration purposes.

{"title":"In-silico color prediction process for natural dyes in Madder","authors":"Thanh Huyen Linh Tran , Romain Berraud-Pache , Maguy Jaber","doi":"10.1016/j.dyepig.2025.112701","DOIUrl":"10.1016/j.dyepig.2025.112701","url":null,"abstract":"<div><div>In the field of cultural heritage, accurately identifying the colors produced by madder root dyes without alteration is critical. In fact, textile dyeing using extracts from their roots has been performed for centuries. Many examples of madder dye remain today in museum and conservation collections. Madder is an interesting natural source of dye because it contains up to 68 different colorants. However, many of these dyes are extremely sensitive to hydrolysis, decarboxylation, and degradation from enzymes, extraction chemicals, and processing temperatures. The valuable chemical information embedded in the dye structure may be lost if extraction and analysis are too harsh, resulting in inaccurate color prediction with large color differences. Thus, they are often overlooked as colorants in historical textiles. Over the past decades, traditional extraction techniques have been used to analyze textiles but they are invasive and destructive. As a result, this method is expensive, time-consuming, and in some cases is not suited for the analysis of artwork. But in the last decades, computer techniques have been presented as a powerful tool that enables the prediction of UV–VIS signature spectra and color coordinates with high accuracy using Time-Dependent Density Functional Theory. The aim of this study is to elaborate an efficient color prediction process of madder's root without any chemical degradation of dyes. It will enable the creation of a robust analytical database to identify madder colors in heritage objects. Here, we provide a rapid method to obtain a complete database of predicted UV–VIS spectra and color of anthraquinone derivatives found in Madder. In the context of historical textiles, the detailed color of natural colorants present in the artwork is of paramount importance for conservation and restoration purposes.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"237 ","pages":"Article 112701"},"PeriodicalIF":4.1,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143429808","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 of carboxylic acid N-hydroxysuccinimidyl ester dyes and their reactive dyeing on silk fibroin

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-13 DOI: 10.1016/j.dyepig.2025.112696

Tingye Gu , Qing Guo , Dongming Qi , Pu Gao , Weiguo Chen , Zhihua Cui , Sateesh Bandaru

N-hydroxysuccinimide esters (NHS esters) are widely recognized as amine-reactive compounds due to their mild reaction conditions and high efficiency. In this study, NHS ester group was introduced into the dye chromophores to design and synthesize carboxylic acid succinimidyl ester dyes (CSEDs) in red, yellow and blue colors. The CSEDs were characterized using high-resolution mass spectrometry, proton nuclear magnetic resonance, and infrared spectroscopy. When the NHS ester group was introduced, UV–vis absorption spectroscopy only slightly affected the molar extinction coefficient and maximal absorption wavelength. Hydrolysis studies demonstrated that CSEDs hydrolyzed slowly in acidic environments but quickly in weakly alkaline ones, with near-complete hydrolysis taking place at pH 8.5 after half an hour. It was discovered that CSEDs could successfully dye silk fibroin at room temperature in weakly alkaline conditions, producing a high color depth and more than 95 % color fixing. The binding of CSEDs to silk fibroin was confirmed through covalent bonds using DMF stripping method and dialysis method. Furthermore, the color fastness of dyed silk fibroin to washing and rubbing was rated above grade 4–5. Compared to commercial dyes, the milder dyeing conditions of CSEDs can save energy and did not require a significant amount of salt to promote the dyeing process.

{"title":"Synthesis of carboxylic acid N-hydroxysuccinimidyl ester dyes and their reactive dyeing on silk fibroin","authors":"Tingye Gu , Qing Guo , Dongming Qi , Pu Gao , Weiguo Chen , Zhihua Cui , Sateesh Bandaru","doi":"10.1016/j.dyepig.2025.112696","DOIUrl":"10.1016/j.dyepig.2025.112696","url":null,"abstract":"<div><div><em>N</em>-hydroxysuccinimide esters (NHS esters) are widely recognized as amine-reactive compounds due to their mild reaction conditions and high efficiency. In this study, NHS ester group was introduced into the dye chromophores to design and synthesize carboxylic acid succinimidyl ester dyes (<strong>CSED</strong>s) in red, yellow and blue colors. The <strong>CSED</strong>s were characterized using high-resolution mass spectrometry, proton nuclear magnetic resonance, and infrared spectroscopy. When the NHS ester group was introduced, UV–vis absorption spectroscopy only slightly affected the molar extinction coefficient and maximal absorption wavelength. Hydrolysis studies demonstrated that <strong>CSED</strong>s hydrolyzed slowly in acidic environments but quickly in weakly alkaline ones, with near-complete hydrolysis taking place at pH 8.5 after half an hour. It was discovered that <strong>CSED</strong>s could successfully dye silk fibroin at room temperature in weakly alkaline conditions, producing a high color depth and more than 95 % color fixing. The binding of <strong>CSED</strong>s to silk fibroin was confirmed through covalent bonds using DMF stripping method and dialysis method. Furthermore, the color fastness of dyed silk fibroin to washing and rubbing was rated above grade 4–5. Compared to commercial dyes, the milder dyeing conditions of <strong>CSED</strong>s can save energy and did not require a significant amount of salt to promote the dyeing process.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"238 ","pages":"Article 112696"},"PeriodicalIF":4.1,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143471406","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

Atom-efficient and self-delivered prodrug based on methylene blue and doxorubicin for tumor combination therapy

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-13 DOI: 10.1016/j.dyepig.2025.112699

Yuchen Song , Qiang Wang , Qiankun Shi , Tongyin Xiong , Biru Wu , Jucai Gao , Fang Hu

Traditional cancer treatments often lead to significant side effects and exhibit limited circulation within the body. To address these issues, considerable efforts have been directed towards developing drug delivery systems and prodrug strategies. However, the inclusion of supplementary carrier materials and protective groups complicates the clinical transition process. Here, we introduce a prodrug nano-assembly formed by conjugating methylene blue (MB) and doxorubicin (DOX) through a urea linkage. Notably, the resulting MB-DOX structure incorporates only 1.9 % additional atoms compared to clinical MB and DOX. This formulation effectively masks the cytotoxicity of DOX and eliminates the photosensitivity of MB. Moreover, the amphiphilic nature of MB-DOX facilitates self-assembly into nanostructures without requiring additional carriers, realizing self-delivery. Upon accumulation at the tumor site, light-induced cleavage of the urea bond releases therapeutic MB and DOX, enabling combined photodynamic therapy and chemotherapy with minimal adverse effects. Crucially, our design fulfills self-delivery and reduces the side effects of MB and DOX by simply introducing a urea linkage, eliminating the necessity for carrier materials and bulk protective groups, and holding promise for expediting the clinical translation of prodrugs.

{"title":"Atom-efficient and self-delivered prodrug based on methylene blue and doxorubicin for tumor combination therapy","authors":"Yuchen Song , Qiang Wang , Qiankun Shi , Tongyin Xiong , Biru Wu , Jucai Gao , Fang Hu","doi":"10.1016/j.dyepig.2025.112699","DOIUrl":"10.1016/j.dyepig.2025.112699","url":null,"abstract":"<div><div>Traditional cancer treatments often lead to significant side effects and exhibit limited circulation within the body. To address these issues, considerable efforts have been directed towards developing drug delivery systems and prodrug strategies. However, the inclusion of supplementary carrier materials and protective groups complicates the clinical transition process. Here, we introduce a prodrug nano-assembly formed by conjugating methylene blue (MB) and doxorubicin (DOX) through a urea linkage. Notably, the resulting MB-DOX structure incorporates only 1.9 % additional atoms compared to clinical MB and DOX. This formulation effectively masks the cytotoxicity of DOX and eliminates the photosensitivity of MB. Moreover, the amphiphilic nature of MB-DOX facilitates self-assembly into nanostructures without requiring additional carriers, realizing self-delivery. Upon accumulation at the tumor site, light-induced cleavage of the urea bond releases therapeutic MB and DOX, enabling combined photodynamic therapy and chemotherapy with minimal adverse effects. Crucially, our design fulfills self-delivery and reduces the side effects of MB and DOX by simply introducing a urea linkage, eliminating the necessity for carrier materials and bulk protective groups, and holding promise for expediting the clinical translation of prodrugs.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"237 ","pages":"Article 112699"},"PeriodicalIF":4.1,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143429802","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

Corrigendum to “Thermo-optical characterization of fluorescent materials based on edible vegetable oils” [Dyes and Pigments 236 (2025) 112662]

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-02-12 DOI: 10.1016/j.dyepig.2025.112698

Teófanes B. Serna, Dora G. Felipe, Acácio A. Andrade, Viviane Pilla

引用次数: 0

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