Pub Date : 2025-03-06DOI: 10.1016/j.dyepig.2025.112739
Shi-Wei Fu , Zong-Xing Huang , Chuan-Zhi Ni , Fang-Qi Zhang , Yang Li , Yuan-Yuan Zhu , Qi Sun , Shuang-Xi Gu
Binaphthyl-based chiral fluorescent probes (S)-/(R)-1 featuring a 2-methylthiophenimide unit were designed and synthesized. The fluorescent response to enantiomer pairs of amino acids revealed that (S)- and (R)-enantimer of the probe had chiral bias to L- and d-amino acids, respectively. The compound (S)-1 showed outstanding enantioselective fluorescence enhancement toward 10 amino acids (Asn, Glu, Val, Leu, Met, Ser, Gln, Arg, Phe and Ala) in both solvents of EtOH/H2O and DMSO/H2O at the condition of pH 7.5. Extremely high enantiomeric fluorescence enhancement ratio (ef, [IL-I0]/[ID-I0]) were obtained for Asn (646.2), Glu (318.9), Val (255.6), Leu (252.4), Thr (223.9) in EtOH/H2O, and the ef values to Val, Ala, Ser, Glu, Arg, Gln were all larger than 20 in DMSO/H2O. Chiral fluorescent imaging of the four amino acids (Ser, Val, Arg and Gln) were obtained in both living cells and zebrafishes via the probe (R)-1, which provides a new concept for the diagnosis and treatment of diseases associated with amino acid racemization. Results of 1H NMR and HRMS revealed the enantioselective fluorescence enhancement mechanism.
{"title":"A fluorescent probe for enantioselective recognition of amino acids in solutions, cells and zebrafishes","authors":"Shi-Wei Fu , Zong-Xing Huang , Chuan-Zhi Ni , Fang-Qi Zhang , Yang Li , Yuan-Yuan Zhu , Qi Sun , Shuang-Xi Gu","doi":"10.1016/j.dyepig.2025.112739","DOIUrl":"10.1016/j.dyepig.2025.112739","url":null,"abstract":"<div><div>Binaphthyl-based chiral fluorescent probes (<em>S</em>)-/(<em>R</em>)-<strong>1</strong> featuring a 2-methylthiophenimide unit were designed and synthesized. The fluorescent response to enantiomer pairs of amino acids revealed that (<em>S</em>)- and (<em>R</em>)-enantimer of the probe had chiral bias to L- and <span>d</span>-amino acids, respectively. The compound (<em>S</em>)-<strong>1</strong> showed outstanding enantioselective fluorescence enhancement toward 10 amino acids (Asn, Glu, Val, Leu, Met, Ser, Gln, Arg, Phe and Ala) in both solvents of EtOH/H<sub>2</sub>O and DMSO/H<sub>2</sub>O at the condition of pH 7.5. Extremely high enantiomeric fluorescence enhancement ratio (<em>ef</em>, [I<sub>L</sub>-I<sub>0</sub>]/[I<sub>D</sub>-I<sub>0</sub>]) were obtained for Asn (646.2), Glu (318.9), Val (255.6), Leu (252.4), Thr (223.9) in EtOH/H<sub>2</sub>O, and the <em>ef</em> values to Val, Ala, Ser, Glu, Arg, Gln were all larger than 20 in DMSO/H<sub>2</sub>O. Chiral fluorescent imaging of the four amino acids (Ser, Val, Arg and Gln) were obtained in both living cells and zebrafishes <em>via</em> the probe (<em>R</em>)-<strong>1</strong>, which provides a new concept for the diagnosis and treatment of diseases associated with amino acid racemization. Results of <sup>1</sup>H NMR and HRMS revealed the enantioselective fluorescence enhancement mechanism.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112739"},"PeriodicalIF":4.1,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143579802","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 : 2025-03-05DOI: 10.1016/j.dyepig.2025.112738
Yuanyuan Zhou , Yaohua Shi , Miao Li , Xingjie Wang , Qianqian Zhu , Ziyou Duan , Lulu Jiang , Jien Yang , Chaochao Qin , Ruiping Qin
aliphatic amine-functionalized perylene-diimide (PDINN) has strong unique hydrogen-bonding and electron self-doping effect so that it accelerates the leapfrog speed of organic solar cells (OSCs) efficiency to the highest present level. Here the dye, PDINN is modified by dicarboxylate and tetra-phenyl-phosphonium moieties obtaining two cathode interfacial materials PDOEN and PDOP. PDOEN is still retaining half aliphatic amine-function-group like PDINN; PDOP furnished with tetra-phenyl-phosphonium bromide. The two interfacial materials tuned the surface wettability, energy level alignment and physical contact properties, leading to device performance improvement. The power conversion efficiency was promoted from 15.43 % of PDINN based OSCs to 15.88 % of PDOEN based OSCs with PM6/Y6 as photo active system. For another photo active system PM6/L8-BO, this parameter also enhanced from 17.13 % (PDINN device) up to 17.45 % (PDOEN device). Except for the open circuit voltage, the photo current increasement is noteworthy and can be observed visually by photo-current map technology. The property of the two PDI-derivatives indicates that ester imide structures could be useful protocol in developing high-performance organic interlayer materials.
{"title":"Interlayer enhancement of organic solar cells efficiency","authors":"Yuanyuan Zhou , Yaohua Shi , Miao Li , Xingjie Wang , Qianqian Zhu , Ziyou Duan , Lulu Jiang , Jien Yang , Chaochao Qin , Ruiping Qin","doi":"10.1016/j.dyepig.2025.112738","DOIUrl":"10.1016/j.dyepig.2025.112738","url":null,"abstract":"<div><div>aliphatic amine-functionalized perylene-diimide (PDINN) has strong unique hydrogen-bonding and electron self-doping effect so that it accelerates the leapfrog speed of organic solar cells (OSCs) efficiency to the highest present level. Here the dye, PDINN is modified by dicarboxylate and tetra-phenyl-phosphonium moieties obtaining two cathode interfacial materials PDOEN and PDOP. PDOEN is still retaining half aliphatic amine-function-group like PDINN; PDOP furnished with tetra-phenyl-phosphonium bromide. The two interfacial materials tuned the surface wettability, energy level alignment and physical contact properties, leading to device performance improvement. The power conversion efficiency was promoted from 15.43 % of PDINN based OSCs to 15.88 % of PDOEN based OSCs with PM6/Y6 as photo active system. For another photo active system PM6/L8-BO, this parameter also enhanced from 17.13 % (PDINN device) up to 17.45 % (PDOEN device). Except for the open circuit voltage, the photo current increasement is noteworthy and can be observed visually by photo-current map technology. The property of the two PDI-derivatives indicates that ester imide structures could be useful protocol in developing high-performance organic interlayer materials.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112738"},"PeriodicalIF":4.1,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143579801","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 : 2025-03-05DOI: 10.1016/j.dyepig.2025.112734
Hao Xue , Hong Zheng , Jing Xiang , Ke Cheng , Biyue Zhu
In this work, using discarded white pomelo peel as the green precursor and hydrochloric acid (HCl) as the dopant, water-soluble Cl–N-doped carbon dots (Cl-NCDs) with excellent performance were synthesized by one-step hydrothermal method. The Cl-NCDs function as both luminescent agents and catalysts, significantly enhancing the chemiluminescence intensity of the HCl–HCHO–KMnO4 system, forming a novel HCl–HCHO-(Cl-NCDs)-KMnO4 chemiluminescence system. The addition of erythromycin (EM) solution inhibits the chemiluminescence intensity of new system. By optimizing the conditions, we established a simple, cost-effective, and reliable chemiluminescence method for EM detection, offering a linear range of 5–100 μM and a detection limit of 0.0149 μM. In addition, this method was successfully applied to the analysis of EM in various water simples, achieving recovery rates ranging from 97.6 % to 106 %.
{"title":"Chemiluminescence of Cl-NCDs and KMnO4 systems based on waste pomelo peel for erythromycin detection","authors":"Hao Xue , Hong Zheng , Jing Xiang , Ke Cheng , Biyue Zhu","doi":"10.1016/j.dyepig.2025.112734","DOIUrl":"10.1016/j.dyepig.2025.112734","url":null,"abstract":"<div><div>In this work, using discarded white pomelo peel as the green precursor and hydrochloric acid (HCl) as the dopant, water-soluble Cl–N-doped carbon dots (Cl-NCDs) with excellent performance were synthesized by one-step hydrothermal method. The Cl-NCDs function as both luminescent agents and catalysts, significantly enhancing the chemiluminescence intensity of the HCl–HCHO–KMnO<sub>4</sub> system, forming a novel HCl–HCHO-(Cl-NCDs)-KMnO<sub>4</sub> chemiluminescence system. The addition of erythromycin (EM) solution inhibits the chemiluminescence intensity of new system. By optimizing the conditions, we established a simple, cost-effective, and reliable chemiluminescence method for EM detection, offering a linear range of 5–100 μM and a detection limit of 0.0149 μM. In addition, this method was successfully applied to the analysis of EM in various water simples, achieving recovery rates ranging from 97.6 % to 106 %.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112734"},"PeriodicalIF":4.1,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143637619","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 : 2025-03-03DOI: 10.1016/j.dyepig.2025.112737
Di Wu, Chengpei Du, Lingyan Ma, Rui Xiao, Long Tan, Wenjing Qi
Owing to Zn2+-sensitized fluorescent effect, boric acid functionalized zinc-europium binuclear metal-organic frameworks (Zn-Eu-MOFs) are synthesized and applied in fluorescent quenching detection of luteolin in Chrysanthemum tea for the first time. Eu3+/Zn2+ and 5-boronobenzene-1,3-dicarboxylic acid (BBDC) are utilized via a fast one-pot microwave process at 120 °C for 1 h. Due to energy transfer efficiency change by “antenna” effect and better effective energy transfer of Zn2+ than Eu3+, Zn2+ increases fluorescence of Zn-Eu-MOFs nearly 3.5 times. Different ligands and different metal ions are compared to synthesize Zn-Eu-MOFs. Highly specific binding affinity of boric acid towards cis-diol structure in luteolin and chelating of Zn2+ with luteolin achieves fluorescent quenching detection of luteolin with low limit of detection of 16 nΜ and high selectivity. When it is utilized in fluorescent detection of luteolin in water and Chrysanthemum tea, mean recoveries are obtained from 99.5 % to 102.7 % and from 99.3 % to 100.6 %, respectively.
{"title":"Fluorescent sensitive detection of luteolin in Chrysanthemum tea using boric acid functionalized binuclear Zn-Eu-MOFs","authors":"Di Wu, Chengpei Du, Lingyan Ma, Rui Xiao, Long Tan, Wenjing Qi","doi":"10.1016/j.dyepig.2025.112737","DOIUrl":"10.1016/j.dyepig.2025.112737","url":null,"abstract":"<div><div>Owing to Zn<sup>2+</sup>-sensitized fluorescent effect, boric acid functionalized zinc-europium binuclear metal-organic frameworks (<strong>Zn-Eu-MOFs</strong>) are synthesized and applied in fluorescent quenching detection of luteolin in <em>Chrysanthemum</em> tea for the first time. Eu<sup>3+</sup>/Zn<sup>2+</sup> and 5-boronobenzene-1,3-dicarboxylic acid (BBDC) are utilized via a fast one-pot microwave process at 120 °C for 1 h. Due to energy transfer efficiency change by “antenna” effect and better effective energy transfer of Zn<sup>2+</sup> than Eu<sup>3+</sup>, Zn<sup>2+</sup> increases fluorescence of <strong>Zn-Eu-MOFs</strong> nearly 3.5 times. Different ligands and different metal ions are compared to synthesize <strong>Zn-Eu-MOFs</strong>. Highly specific binding affinity of boric acid towards cis-diol structure in luteolin and chelating of Zn<sup>2+</sup> with luteolin achieves fluorescent quenching detection of luteolin with low limit of detection of 16 nΜ and high selectivity. When it is utilized in fluorescent detection of luteolin in water and <em>Chrysanthemum</em> tea, mean recoveries are obtained from 99.5 % to 102.7 % and from 99.3 % to 100.6 %, respectively.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"238 ","pages":"Article 112737"},"PeriodicalIF":4.1,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143549198","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 : 2025-03-01DOI: 10.1016/j.dyepig.2025.112722
Hwan Hee Jo , Hyun-Jung Lee , Junmo Kang , Shin Yeong Kim , Seok-In Na , Kyukwan Zong
Centrally extended phenazine-based acceptor units were synthesized for use as conjugated donor polymers in polymer solar cells. These phenazine-derived acceptor units were synthesized through two distinct pathways. In the first route, 2,3-dichloro-6,7-difluoroquinoxaline underwent a Stille reaction to produce 6,7-difluoro-2,3-di(thiophen-3-yl)quinoxaline, which was further subjected to FeCl3-mediated oxidative coupling to yield 9,10-difluorodithieno [3,2-a:2′,3′-c]phenazine. In the second route, 1,2-di(thiophen-3-yl)ethane-1,2-dione was converted into benzo [1,2-b:6,5-b']dithiophene-4,5-dione via FeCl3-mediated oxidative coupling, followed by condensation with 4,5-difluorobenzene-1,2-diamine to obtain 9,10-difluorodithieno [3,2-a:2′,3′-c]phenazine. Polymerization of these acceptors with BDT-Cl in the presence of a Pd (0) catalyst produced two donor-acceptor polymers, PPB-F and PPB, respectively. PPB-F and PPB exhibited excellent thermal stability with decomposition temperatures of 401.95 °C and 387.37 °C, respectively and have strong absorption in the wavelength range of 430–680 nm. Their optical bandgaps were determined as 1.82 eV and 1.83 eV, respectively. Both polymers displayed deeply lying HOMO levels, calculated at 5.42 eV for PPB and 5.57 eV for PPB-F. Devices fabricated and optimized from PPB-F:Y-7 and PPB-F:PC60BM demonstrated power conversion efficiencies (PCEs) of 4.36 % and 3.56 %, respectively.
{"title":"Design, synthesis, and photovoltaic characterization of centrally extended donor-acceptor polymer donors incorporating phenazine derivatives","authors":"Hwan Hee Jo , Hyun-Jung Lee , Junmo Kang , Shin Yeong Kim , Seok-In Na , Kyukwan Zong","doi":"10.1016/j.dyepig.2025.112722","DOIUrl":"10.1016/j.dyepig.2025.112722","url":null,"abstract":"<div><div>Centrally extended phenazine-based acceptor units were synthesized for use as conjugated donor polymers in polymer solar cells. These phenazine-derived acceptor units were synthesized through two distinct pathways. In the first route, 2,3-dichloro-6,7-difluoroquinoxaline underwent a Stille reaction to produce 6,7-difluoro-2,3-di(thiophen-3-yl)quinoxaline, which was further subjected to FeCl<sub>3</sub>-mediated oxidative coupling to yield 9,10-difluorodithieno [3,2-<em>a</em>:2′,3′-<em>c</em>]phenazine. In the second route, 1,2-di(thiophen-3-yl)ethane-1,2-dione was converted into benzo [1,2-<em>b</em>:6,5-<em>b'</em>]dithiophene-4,5-dione via FeCl<sub>3</sub>-mediated oxidative coupling, followed by condensation with 4,5-difluorobenzene-1,2-diamine to obtain 9,10-difluorodithieno [3,2-<em>a</em>:2′,3′-<em>c</em>]phenazine. Polymerization of these acceptors with BDT-Cl in the presence of a Pd (0) catalyst produced two donor-acceptor polymers, PPB-F and PPB, respectively. PPB-F and PPB exhibited excellent thermal stability with decomposition temperatures of 401.95 °C and 387.37 °C, respectively and have strong absorption in the wavelength range of 430–680 nm. Their optical bandgaps were determined as 1.82 eV and 1.83 eV, respectively. Both polymers displayed deeply lying HOMO levels, calculated at 5.42 eV for PPB and 5.57 eV for PPB-F. Devices fabricated and optimized from PPB-F:Y-7 and PPB-F:PC<sub>60</sub>BM demonstrated power conversion efficiencies (PCEs) of 4.36 % and 3.56 %, respectively.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112722"},"PeriodicalIF":4.1,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552520","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 : 2025-02-28DOI: 10.1016/j.dyepig.2025.112735
Kai Jiang , Yao Huang , Zhaodi Wang , Xiang Tian , Aihua Wu , Weihong Liang , Bo Liu
Indole is widely acknowledged as a donor group in molecular luminescent materials such as dyes, probes, biomarkers and organic conductors due to its electron-rich and stable chemical properties. In order to acquire the best fluorescence properties, the structural extension of indole to the construction of donor−acceptor fluorophores should consider the substitution site on the indole ring. Herein, the indole-based positional isomers (3a−3f) with stationary acceptor structures and typical push-pull feature were utilized to describe their difference on fluorescence properties. The results have shown that the C4 isomer 3c is of the longest maximal emission wavelength, while the C6 isomer 3e is of the highest fluorescence quantum yield. Structural derivatives based on the skeleton of 3c and 3e were provided for (i) a NIR fluorophore (4), and (ii) a biocompatible fluorophore (5) resulting from the enhanced solubility and the avoidance of heavy counterion, following by its application in cell imaging.
{"title":"Understanding the effect of indole as a donor in fluorophores by the localization of acceptor","authors":"Kai Jiang , Yao Huang , Zhaodi Wang , Xiang Tian , Aihua Wu , Weihong Liang , Bo Liu","doi":"10.1016/j.dyepig.2025.112735","DOIUrl":"10.1016/j.dyepig.2025.112735","url":null,"abstract":"<div><div>Indole is widely acknowledged as a donor group in molecular luminescent materials such as dyes, probes, biomarkers and organic conductors due to its electron-rich and stable chemical properties. In order to acquire the best fluorescence properties, the structural extension of indole to the construction of donor−acceptor fluorophores should consider the substitution site on the indole ring. Herein, the indole-based positional isomers (<strong>3a</strong>−<strong>3f</strong>) with stationary acceptor structures and typical push-pull feature were utilized to describe their difference on fluorescence properties. The results have shown that the C4 isomer <strong>3c</strong> is of the longest maximal emission wavelength, while the C6 isomer <strong>3e</strong> is of the highest fluorescence quantum yield. Structural derivatives based on the skeleton of <strong>3c</strong> and <strong>3e</strong> were provided for (i) a NIR fluorophore (<strong>4</strong>), and (ii) a biocompatible fluorophore (<strong>5</strong>) resulting from the enhanced solubility and the avoidance of heavy counterion, following by its application in cell imaging.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112735"},"PeriodicalIF":4.1,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552521","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 : 2025-02-28DOI: 10.1016/j.dyepig.2025.112736
Meng-yan Chai , Thayalan Rajeshkumar , Hui Su , Fu-jie Zhao , Zhi Wang , Wei-ping Yin , Song Jiang , Guo-xing Liu , Li-jie Liu , Xin Zheng , Li-xia Xie , Sheng-qiang Guo , Yu-qiang Xiang , Laurent Maron , Cao-yuan Niu
The poor aqueous solubility of porphyrins and metalloporphyrins has long impeded their applications in biological systems. In this study, we report the synthesis of a novel porphyrin derivative—ZnTSPP—achieved by introducing four sulfonic acid groups onto a single porphyrin molecule. The photophysical properties were comprehensively characterized via UV–Vis absorption and fluorescence emission spectroscopy in deionized water, phosphate-buffered saline (PBS), and fetal bovine serum (FBS). ZnTSPP exhibits intense absorption in both the Soret and Q bands and displays a reversible pH response. Density Functional Theory (DFT) calculations further corroborate the pH-dependent formation of J- and H-aggregates. Additionally, cellular imaging studies performed on pig kidney epithelial cells (LLC-PK1) demonstrate that ZnTSPP is not only pH-responsive but also an efficient singlet oxygen generator. These attributes position ZnTSPP as a promising agent for biomedical imaging and photodynamic therapy.
{"title":"A new sulfonic-substituted Zinc(II)-Porphyrin with high aqueous solubility: Synthesis, photophysical properties and application in porcine cell-imaging","authors":"Meng-yan Chai , Thayalan Rajeshkumar , Hui Su , Fu-jie Zhao , Zhi Wang , Wei-ping Yin , Song Jiang , Guo-xing Liu , Li-jie Liu , Xin Zheng , Li-xia Xie , Sheng-qiang Guo , Yu-qiang Xiang , Laurent Maron , Cao-yuan Niu","doi":"10.1016/j.dyepig.2025.112736","DOIUrl":"10.1016/j.dyepig.2025.112736","url":null,"abstract":"<div><div>The poor aqueous solubility of porphyrins and metalloporphyrins has long impeded their applications in biological systems. In this study, we report the synthesis of a novel porphyrin derivative—ZnTSPP—achieved by introducing four sulfonic acid groups onto a single porphyrin molecule. The photophysical properties were comprehensively characterized via UV–Vis absorption and fluorescence emission spectroscopy in deionized water, phosphate-buffered saline (PBS), and fetal bovine serum (FBS). ZnTSPP exhibits intense absorption in both the Soret and Q bands and displays a reversible pH response. Density Functional Theory (DFT) calculations further corroborate the pH-dependent formation of J- and H-aggregates. Additionally, cellular imaging studies performed on pig kidney epithelial cells (LLC-PK1) demonstrate that ZnTSPP is not only pH-responsive but also an efficient singlet oxygen generator. These attributes position ZnTSPP as a promising agent for biomedical imaging and photodynamic therapy.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"238 ","pages":"Article 112736"},"PeriodicalIF":4.1,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143534760","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 : 2025-02-27DOI: 10.1016/j.dyepig.2025.112732
Byung Kyu Jeon , Seong Hyun Jang , Se Hun Kim , Hoseong Lee , In Choi , Byoung-Sun Lee , Keehoon Kang , Jun Choi
In this study, we developed novel red azo dyes applicable to color conversion layers with a wide color reproduction range, utilized in micropixel white organic light-emitting diodes. We introduced strong electron-withdrawing groups at the diazo component with the aim of controlling electron flow within the molecules and achieving a superior molar absorption coefficient. The introduction of these groups also resulted in a decrease in the lowest unoccupied molecular orbital energy level, leading to a red shift in the absorption wavelength, thus anticipating a broader color reproduction range. Subsequently, we prepared the color resists by combining the novel red azo dyes with a low-temperature-curing binder, producing color conversion films through spin coating. These spin-coated films exhibited high transmittance of up to 99 %, indicating the optimal formulation of the color resist components. Additionally, the introduction of a yellow color-tuning dye, structurally similar to the novel red dyes, broadened the color reproduction range to 111 % of the National Television System Committee color coordinates. The photostability tests conducted on the prepared spin-coated films exhibited minuscule variations in transmittance, indicating the simultaneous enhancement of the optical properties and photostability of the prepared microdisplay color conversion layers.
{"title":"Development of electron-flow-strengthened azo dyes with a wide color reproduction range for application in the color conversion layers of microdisplays","authors":"Byung Kyu Jeon , Seong Hyun Jang , Se Hun Kim , Hoseong Lee , In Choi , Byoung-Sun Lee , Keehoon Kang , Jun Choi","doi":"10.1016/j.dyepig.2025.112732","DOIUrl":"10.1016/j.dyepig.2025.112732","url":null,"abstract":"<div><div>In this study, we developed novel red azo dyes applicable to color conversion layers with a wide color reproduction range, utilized in micropixel white organic light-emitting diodes. We introduced strong electron-withdrawing groups at the diazo component with the aim of controlling electron flow within the molecules and achieving a superior molar absorption coefficient. The introduction of these groups also resulted in a decrease in the lowest unoccupied molecular orbital energy level, leading to a red shift in the absorption wavelength, thus anticipating a broader color reproduction range. Subsequently, we prepared the color resists by combining the novel red azo dyes with a low-temperature-curing binder, producing color conversion films through spin coating. These spin-coated films exhibited high transmittance of up to 99 %, indicating the optimal formulation of the color resist components. Additionally, the introduction of a yellow color-tuning dye, structurally similar to the novel red dyes, broadened the color reproduction range to 111 % of the National Television System Committee color coordinates. The photostability tests conducted on the prepared spin-coated films exhibited minuscule variations in transmittance, indicating the simultaneous enhancement of the optical properties and photostability of the prepared microdisplay color conversion layers.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"238 ","pages":"Article 112732"},"PeriodicalIF":4.1,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143534761","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 : 2025-02-27DOI: 10.1016/j.dyepig.2025.112733
Nicolò Guarnieri , Alessia Di Benedetto , Daniela Comelli , Francesco Mirani , David Dellasega , Laura Pagnin , Sara Goidanich , Lucia Toniolo
Over the last few years, contemporary mural paintings have gained significant importance as both artistic and social expressions within urban environments. The study focuses on the characterization of the faded painting materials from a case study in Milan, 20 years of Freedom and Democracy, and its aesthetic, morphological and chemical alterations. The goal is to study the phenomenon of chromatic alteration and understanding causes and mechanisms. In this work, a diagnostic study based on non-destructive and micro-destructive investigation methods is presented, improving and integrating the knowledge about Street Art deterioration. The colour fading of this mural was clearly evident from the available online photographic documentation, which allowed the reconstruction of the evolution of its appearance over time since its realization. The analysis revealed that colour fading occurred within the first two years. A wide range of analytical techniques were employed to gain deeper insights into the qualitative and semi-quantitative composition of the materials. These included hyperspectral imaging, microscopy observations and molecular and elemental spectroscopies of collected paint samples (μ-FTIR ATR and reflectance mapping, μ-Raman spectroscopy, FE-SEM observation and EDXS mapping). Colour fading was found to affect less than 10 μm of the surface. The deterioration of the polymeric binder promotes the loss of pigments and therefore the enrichment of white fillers on the surface, the so-called chalking effect, in agreement with other studies on Street Art murals. Furthermore, the photochemical instability of specific pigments (PR112, C.I.:12370 and PY83, C.I.:21108) was demonstrated, leading to the dramatic colour changes observed on the real surface.
{"title":"Rapid chromatic alteration of Street Art: Mechanisms of deterioration of the painting materials of the 20 years of Freedom and Democracy mural","authors":"Nicolò Guarnieri , Alessia Di Benedetto , Daniela Comelli , Francesco Mirani , David Dellasega , Laura Pagnin , Sara Goidanich , Lucia Toniolo","doi":"10.1016/j.dyepig.2025.112733","DOIUrl":"10.1016/j.dyepig.2025.112733","url":null,"abstract":"<div><div>Over the last few years, contemporary mural paintings have gained significant importance as both artistic and social expressions within urban environments. The study focuses on the characterization of the faded painting materials from a case study in Milan, <em>20 years of Freedom and Democracy,</em> and its aesthetic, morphological and chemical alterations. The goal is to study the phenomenon of chromatic alteration and understanding causes and mechanisms. In this work, a diagnostic study based on non-destructive and micro-destructive investigation methods is presented, improving and integrating the knowledge about Street Art deterioration. The colour fading of this mural was clearly evident from the available online photographic documentation, which allowed the reconstruction of the evolution of its appearance over time since its realization. The analysis revealed that colour fading occurred within the first two years. A wide range of analytical techniques were employed to gain deeper insights into the qualitative and semi-quantitative composition of the materials. These included hyperspectral imaging, microscopy observations and molecular and elemental spectroscopies of collected paint samples (μ-FTIR ATR and reflectance mapping, μ-Raman spectroscopy, FE-SEM observation and EDXS mapping). Colour fading was found to affect less than 10 μm of the surface. The deterioration of the polymeric binder promotes the loss of pigments and therefore the enrichment of white fillers on the surface, the so-called chalking effect, in agreement with other studies on Street Art murals. Furthermore, the photochemical instability of specific pigments (PR112, C.I.:12370 and PY83, C.I.:21108) was demonstrated, leading to the dramatic colour changes observed on the real surface.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112733"},"PeriodicalIF":4.1,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143562840","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}
Two novel binuclear platinum(II) complexes with different embedded units and the same donor (D)/acceptor (A) termini of triphenylamine (TPA) and isoquinoline (iq) in the main ligands, (TPAiq)2Pt2(μ-C8OXT)2 and (TPAniq)2Pt2(μ-C8OXT)2, were designed and synthesized, in which the embedded units are single bond and naphthylidene, respectively. Remarkable photoluminescent properties were observed with photoluminescent quantum yield of 10.5 % at emission peak of 670 nm for (TPAiq)2Pt2(μ-C8OXT)2, and 3.7 % at 732 nm for (TPAniq)2Pt2(μ-C8OXT)2 in the neat films. Their luminescence lifetimes were 840 and 1413 ns, respectively. Meanwhile, the (TPAiq)2Pt2(μ-C8OXT)2 and (TPAniq)2Pt2(μ-C8OXT)2 doped polymer light-emitting devices (PLEDs) further displayed deep-red to near-infrared electroluminescent properties at the emission peaks of 678 nm and 712 nm with the maximum external quantum efficiencies of 2.00 % and 0.26 %, respectively. This work demonstrated new insight for designing deep-red to near-infrared platinum complexes by the embedded strategy in the D-A-type ligands to regulate emission spectrum and efficiency for advanced PLED applications.
{"title":"Cyclometalated binuclear platinum(II) complexes with an embedded D-A ligand as efficient phosphors for NIR-OLEDs","authors":"Wengjing Xiong , Yuanyuan Fang , Fanyuan Meng , Cheng Zhang , Keyue Xu , Jialu Liu , Weiguo Zhu","doi":"10.1016/j.dyepig.2025.112731","DOIUrl":"10.1016/j.dyepig.2025.112731","url":null,"abstract":"<div><div>Two novel binuclear platinum(II) complexes with different embedded units and the same donor (D)/acceptor (A) termini of triphenylamine (TPA) and isoquinoline (iq) in the main ligands, (TPAiq)<sub>2</sub>Pt<sub>2</sub>(<em>μ</em>-C<sub>8</sub>OXT)<sub>2</sub> and (TPAniq)<sub>2</sub>Pt<sub>2</sub>(<em>μ</em>-C<sub>8</sub>OXT)<sub>2</sub>, were designed and synthesized, in which the embedded units are single bond and naphthylidene, respectively. Remarkable photoluminescent properties were observed with photoluminescent quantum yield of 10.5 % at emission peak of 670 nm for (TPAiq)<sub>2</sub>Pt<sub>2</sub>(<em>μ</em>-C<sub>8</sub>OXT)<sub>2</sub>, and 3.7 % at 732 nm for (TPAniq)<sub>2</sub>Pt<sub>2</sub>(<em>μ</em>-C<sub>8</sub>OXT)<sub>2</sub> in the neat films. Their luminescence lifetimes were 840 and 1413 ns, respectively. Meanwhile, the (TPAiq)<sub>2</sub>Pt<sub>2</sub>(<em>μ</em>-C<sub>8</sub>OXT)<sub>2</sub> and (TPAniq)<sub>2</sub>Pt<sub>2</sub>(<em>μ</em>-C<sub>8</sub>OXT)<sub>2</sub> doped polymer light-emitting devices (PLEDs) further displayed deep-red to near-infrared electroluminescent properties at the emission peaks of 678 nm and 712 nm with the maximum external quantum efficiencies of 2.00 % and 0.26 %, respectively. This work demonstrated new insight for designing deep-red to near-infrared platinum complexes by the embedded strategy in the D-A-type ligands to regulate emission spectrum and efficiency for advanced PLED applications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112731"},"PeriodicalIF":4.1,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552519","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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