Pub Date : 2025-04-17DOI: 10.1016/j.dyepig.2025.112841
Ning Wang , Haoyang Li , Demei Kong , Xiaoyue Feng , Chen Li , Xiaoyan Cui , Ting Wang
Fluorescein derivatives, characterized by a xanthene backbone, represent a prominent class of organic molecular dyes. Through silicon atom substitution, silicon-substituted fluoresceins (SiFs) exhibit bathochromic emission spectra with high quantum yields. However, the anionic configuration significantly restricts their application in vivo. Herein, we reported dibutylated silicon fluorescein, SiFC4 and HSiFC4. With increased hydrophobicity by dibutylation, SiFC4 tends to convert into the neutral lactone form and enables its aggregation (150 nm in diameter) with substantially reduced background fluorescence at physiological pH. Notably, HSiFC4 demonstrates 4.3-fold enhanced fluorogenicity in HaloTag labeling systems and robust fluorescence response (4.1-fold) in living cell imaging compared to its dimethyl derivative, HSiFC1. This approach underscores the potential of alkylation in modulating the properties of fluorophores, offering a promising strategy for advanced applications in the future.
{"title":"Dibutylated Si-fluorescein: enhanced hydrophobicity for fluorogenic labeling in vivo","authors":"Ning Wang , Haoyang Li , Demei Kong , Xiaoyue Feng , Chen Li , Xiaoyan Cui , Ting Wang","doi":"10.1016/j.dyepig.2025.112841","DOIUrl":"10.1016/j.dyepig.2025.112841","url":null,"abstract":"<div><div>Fluorescein derivatives, characterized by a xanthene backbone, represent a prominent class of organic molecular dyes. Through silicon atom substitution, silicon-substituted fluoresceins (SiFs) exhibit bathochromic emission spectra with high quantum yields. However, the anionic configuration significantly restricts their application <em>in vivo</em>. Herein, we reported dibutylated silicon fluorescein, <strong>SiFC4</strong> and <strong>HSiFC4</strong>. With increased hydrophobicity by dibutylation, <strong>SiFC4</strong> tends to convert into the neutral lactone form and enables its aggregation (150 nm in diameter) with substantially reduced background fluorescence at physiological pH. Notably, <strong>HSiFC4</strong> demonstrates 4.3-fold enhanced fluorogenicity in HaloTag labeling systems and robust fluorescence response (4.1-fold) in living cell imaging compared to its dimethyl derivative, <strong>HSiFC1</strong>. This approach underscores the potential of alkylation in modulating the properties of fluorophores, offering a promising strategy for advanced applications in the future.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112841"},"PeriodicalIF":4.1,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143850861","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 : 2025-04-16DOI: 10.1016/j.dyepig.2025.112843
Yli Peng , Wenle Wang , Xinyu Li , Yuqin Du , Feng Wang , Kang Chen , Huixia Xu , Huijun Sun , Yanqin Miao , Hua Wang
To enhance and stabilize the performance of organic light emitting diodes (OLEDs), it is essential to design the host to converse dark triplet excitons to emissive singlet. Herein, we developed a host material with thermally activated delayed fluorescence (TADF) characteristics based on phthalonitrile and carbazole derivatives, namely Me-2CzPN. This TADF molecule derived from a typical TADF emitter of 2CzPN through featuring double methyls groups on 3- and 6- positions of carbazole. Me-2CzPN exhibits a high triplet energy of 2.47 eV and a large rate constant of reverse intersystem crossing (RISC), ensuring efficient energy transfer from host to guest, and improve the utilization of triplet exciton. Consequently, the corresponding blue TADF-OLED achieved a high maximum external quantum efficiency () of 20.8 %. When employed Me-2CzPN as a host material in red phosphorescent OLED, the device displayed an of 12.4 %. Furthermore, Me-2CzPN was used sensitizer in hyperfluorescent OLEDs (HF-OLEDs), exhibiting an of 7.1 % accompanied with full width at half maximum (FWHM) values of 34 nm. These findings reveal the versatile applications of Me-2CzPN as emitter, host and sensitizer for fluorescent emitters, respectively.
{"title":"Thermally activated delayed fluorescence material based on phthalonitrile for versatile applications as host and sensitizer in OLEDs","authors":"Yli Peng , Wenle Wang , Xinyu Li , Yuqin Du , Feng Wang , Kang Chen , Huixia Xu , Huijun Sun , Yanqin Miao , Hua Wang","doi":"10.1016/j.dyepig.2025.112843","DOIUrl":"10.1016/j.dyepig.2025.112843","url":null,"abstract":"<div><div>To enhance and stabilize the performance of organic light emitting diodes (OLEDs), it is essential to design the host to converse dark triplet excitons to emissive singlet. Herein, we developed a host material with thermally activated delayed fluorescence (TADF) characteristics based on phthalonitrile and carbazole derivatives, namely Me-2CzPN. This TADF molecule derived from a typical TADF emitter of 2CzPN through featuring double methyls groups on 3- and 6- positions of carbazole. Me-2CzPN exhibits a high triplet energy of 2.47 eV and a large rate constant of reverse intersystem crossing (RISC), ensuring efficient energy transfer from host to guest, and improve the utilization of triplet exciton. Consequently, the corresponding blue TADF-OLED achieved a high maximum external quantum efficiency (<span><math><mrow><msub><mrow><mi>E</mi><mi>Q</mi><mi>E</mi></mrow><mi>max</mi></msub></mrow></math></span>) of 20.8 %. When employed Me-2CzPN as a host material in red phosphorescent OLED, the device displayed an <span><math><mrow><msub><mrow><mi>E</mi><mi>Q</mi><mi>E</mi></mrow><mi>max</mi></msub></mrow></math></span> of 12.4 %. Furthermore, Me-2CzPN was used sensitizer in hyperfluorescent OLEDs (HF-OLEDs), exhibiting an <span><math><mrow><msub><mrow><mi>E</mi><mi>Q</mi><mi>E</mi></mrow><mi>max</mi></msub></mrow></math></span> of 7.1 % accompanied with full width at half maximum (FWHM) values of 34 nm. These findings reveal the versatile applications of Me-2CzPN as emitter, host and sensitizer for fluorescent emitters, respectively.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112843"},"PeriodicalIF":4.1,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847599","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 : 2025-04-15DOI: 10.1016/j.dyepig.2025.112836
Lin Wang , Ning Zhang , Jian-Yong Wang
Hypochlorous acid (HClO), as a kind of reactive oxygen species, was produced in the normal aerobic metabolism of organisms. The right amount of HClO can kill invading organisms and fight infection. However, when the amount of HClO is too high, the homeostasis within cells could be disrupted, resulting in irreversible damage to the body. Therefore, HClO plays an important role in normal physiological activities. In this study, a fluorescent probe BTD-TM for monitoring HClO was designed and developed based on benzothiadiazole. When HClO was recognized, the atom S in the thiomorpholine group was oxidized to the sulfoxide structure. Probe BTD-TM showed the advantages of large Stokes shift (120 nm) with low detection limit (LOD = 0.414 μM), high sensitivity, and good stability. Probe BTD-TM was able to achieve the precise detection of endogenous hypochlorous acid with high sensitivity, covering the intracellular homeostasis response induced by n-acetylcysteine and the inflammatory model system triggered by lipopolysaccharide stimulation. At the same time, excellent detection performance was also demonstrated for the tracking of the addition of exogenous hypochlorous acid. In addition, bioimaging showed that BTD-TM could also be used to detect HClO in zebrafish and tobacco seedlings.
{"title":"A novel fluorescent probe with a large Stokes shift for rapidly monitoring hypochlorous acid in living cells, zebrafish, and tobacco seedlings","authors":"Lin Wang , Ning Zhang , Jian-Yong Wang","doi":"10.1016/j.dyepig.2025.112836","DOIUrl":"10.1016/j.dyepig.2025.112836","url":null,"abstract":"<div><div>Hypochlorous acid (HClO), as a kind of reactive oxygen species, was produced in the normal aerobic metabolism of organisms. The right amount of HClO can kill invading organisms and fight infection. However, when the amount of HClO is too high, the homeostasis within cells could be disrupted, resulting in irreversible damage to the body. Therefore, HClO plays an important role in normal physiological activities. In this study, a fluorescent probe BTD-TM for monitoring HClO was designed and developed based on benzothiadiazole. When HClO was recognized, the atom S in the thiomorpholine group was oxidized to the sulfoxide structure. Probe BTD-TM showed the advantages of large Stokes shift (120 nm) with low detection limit (LOD = 0.414 μM), high sensitivity, and good stability. Probe BTD-TM was able to achieve the precise detection of endogenous hypochlorous acid with high sensitivity, covering the intracellular homeostasis response induced by n-acetylcysteine and the inflammatory model system triggered by lipopolysaccharide stimulation. At the same time, excellent detection performance was also demonstrated for the tracking of the addition of exogenous hypochlorous acid. In addition, bioimaging showed that BTD-TM could also be used to detect HClO in zebrafish and tobacco seedlings.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112836"},"PeriodicalIF":4.1,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876786","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}
Lipid droplets (LDs) are critical organelles that participate in numerous biological processes in eukaryotic cells. However, the unsatisfying specificity to LDs and poor photostability of previous fluorescent probes (e.g. BODIPY 493/503, Nile Red) have substantially limited the in-depth investigations into LDs, particularly for the small and nascent LDs. Herein, inspired by the outstanding photophysical properties of the classical pigment quinacridone (QA), QA was chosen as an excellent π-skeleton to constitute superior fluorescent probe. The indole cores and ether chains were successfully incorporated into its π-skeleton to construct a novel fluorescent probe IQA1. Compared to conventional fluorescent probes, IQA1 not only demonstrates innate superb photostability, but also exhibits superior specificity to LDs. The long ether chains effectively reversed the insolubility of QA in lipids, endowing IQA1 with appropriate lipophilicity to traverse the cell membrane and target LDs. These advantages are conductive to the application of IQA1 in various LDs fluorescence imaging, e.g. 3D confocal imaging of the quantification and dimensions of LDs in the ferroptosis HeLa cells and the oleic acid stimulated HeLa cells, time-lapse structured illumination microscopy (SIM) imaging to observe the dynamics of LDs at nanoscale (178 nm). This study thus not only provides a fascinating fluorescent probe IQA1 for LDs advanced imaging, but also explores a new area for quinacridone pigment application.
脂滴是真核细胞中参与许多生物过程的重要细胞器。然而，以往荧光探针（如BODIPY 493/503， Nile Red）对ld的特异性不理想，光稳定性差，极大地限制了对ld的深入研究，特别是对小型和新生ld的深入研究。本文受经典色素喹吖啶酮（QA）优异的光物理性质的启发，选择QA作为优良的π-骨架来构成优越的荧光探针。将吲哚核和醚链成功地结合到其π-骨架中，构建了新型荧光探针IQA1。与传统荧光探针相比，IQA1不仅具有良好的光稳定性，而且对ld具有优越的特异性。长醚链有效地逆转了QA在脂质中的不溶性，使IQA1具有适当的亲脂性，可以穿过细胞膜和靶ld。这些优点有助于IQA1在各种ld荧光成像中的应用，例如，对铁下垂HeLa细胞和油酸刺激HeLa细胞ld的定量和尺寸的三维共聚焦成像，以及在纳米（178 nm）尺度上观察ld动态的延时结构照明显微镜（SIM）成像。因此，本研究不仅为ld的高级成像提供了一个有吸引力的荧光探针IQA1，而且为喹吖酮色素的应用开辟了新的领域。
{"title":"An indole-fused quinacridone-based fluorescent probe with high photostability and specificity for cellular lipid droplets","authors":"Yutong Ouyang , Haonan Xiong , Huanlong Zheng , Chenguang Wang , Chuandong Dou , Yufei Gao","doi":"10.1016/j.dyepig.2025.112835","DOIUrl":"10.1016/j.dyepig.2025.112835","url":null,"abstract":"<div><div>Lipid droplets (LDs) are critical organelles that participate in numerous biological processes in eukaryotic cells. However, the unsatisfying specificity to LDs and poor photostability of previous fluorescent probes (<em>e.g.</em> BODIPY 493/503, Nile Red) have substantially limited the in-depth investigations into LDs, particularly for the small and nascent LDs. Herein, inspired by the outstanding photophysical properties of the classical pigment quinacridone (QA), QA was chosen as an excellent π-skeleton to constitute superior fluorescent probe. The indole cores and ether chains were successfully incorporated into its π-skeleton to construct a novel fluorescent probe <strong>IQA1</strong>. Compared to conventional fluorescent probes, <strong>IQA1</strong> not only demonstrates innate superb photostability, but also exhibits superior specificity to LDs. The long ether chains effectively reversed the insolubility of QA in lipids, endowing <strong>IQA1</strong> with appropriate lipophilicity to traverse the cell membrane and target LDs. These advantages are conductive to the application of <strong>IQA1</strong> in various LDs fluorescence imaging, <em>e.g.</em> 3D confocal imaging of the quantification and dimensions of LDs in the ferroptosis HeLa cells and the oleic acid stimulated HeLa cells, time-lapse structured illumination microscopy (SIM) imaging to observe the dynamics of LDs at nanoscale (178 nm). This study thus not only provides a fascinating fluorescent probe <strong>IQA1</strong> for LDs advanced imaging, but also explores a new area for quinacridone pigment application.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112835"},"PeriodicalIF":4.1,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143834887","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 : 2025-04-12DOI: 10.1016/j.dyepig.2025.112826
Sumit Kumar , Aditi Arora , Gautam Deo , Mrityunjay K. Tiwari , Jyotirmoy Maity , Brajendra K. Singh
A green, catalyst free, one-pot, gram scale microwave-assisted synthesis of fluorescent furo [3,2-c]quinolone nucleoside analogues has been successfully developed using 2-Me-THF as a greener solvent. This method, employing 3′,5′-di-O-acetyl-5-formyl-2′-deoxyuridine, alkyl isocyanides, and differently substituted 4-hydroxyquinolones, achieved product yield up to 92 %, which offers high atom economy, reduced reaction time and simple work-up procedure. The products were fully characterized by spectroscopic techniques and single crystal X-ray analysis with DFT analysis conforming the electronic structures. Fluorescence studies revealed strong emission (∼450 nm), large Stokes shifts (59–98 nm), and high quantum yields (0.053–0.595). Solvatochromism studies highlighted their environmental sensitivity, indicating potential applications in nucleic acid research and bio-imaging.
{"title":"Microwave-assisted synthesis of base modified Furo[3,2-c]quinolone nucleosides and insights into their photophysical properties","authors":"Sumit Kumar , Aditi Arora , Gautam Deo , Mrityunjay K. Tiwari , Jyotirmoy Maity , Brajendra K. Singh","doi":"10.1016/j.dyepig.2025.112826","DOIUrl":"10.1016/j.dyepig.2025.112826","url":null,"abstract":"<div><div>A green, catalyst free, one-pot, gram scale microwave-assisted synthesis of fluorescent furo [3,2-<em>c</em>]quinolone nucleoside analogues has been successfully developed using 2-Me-THF as a greener solvent. This method, employing 3′,5′-di-<em>O</em>-acetyl-5-formyl-2′-deoxyuridine, alkyl isocyanides, and differently substituted 4-hydroxyquinolones, achieved product yield up to 92 %, which offers high atom economy, reduced reaction time and simple work-up procedure. The products were fully characterized by spectroscopic techniques and single crystal X-ray analysis with DFT analysis conforming the electronic structures. Fluorescence studies revealed strong emission (∼450 nm), large Stokes shifts (59–98 nm), and high quantum yields (0.053–0.595). Solvatochromism studies highlighted their environmental sensitivity, indicating potential applications in nucleic acid research and bio-imaging.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112826"},"PeriodicalIF":4.1,"publicationDate":"2025-04-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143834950","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 : 2025-04-11DOI: 10.1016/j.dyepig.2025.112801
Carla I.M. Santos , Ana M. Santiago , Cristina J. Dias , Ana R. Araújo , Daniel Cavaco , Gonçalo Justino , Manuel Melle-Franco , M. Amparo F. Faustino , M. Graça P.M. S. Neves , JoséM.G. Martinho , Ermelinda M.S. Maçôas
The sensing ability of 2-nitro-5,10,15,20-tetraphenylporphyrin (P–NO2) and of the corresponding Zn(II) complex (ZnP–NO2) towards hydrogen sulfide (H2S) was investigated using UV–vis absorption and emission spectroscopy. The presence of H2S induced strong alterations in the excited state of P–NO2 and ZnP–NO2. Specifically, the originally broad fluorescence emission observed around 700 nm was strongly quenched, while new sharp bands emerged at lower wavelengths. Both P–NO2 and ZnP–NO2 showed a clear sensitive and turn-ON response to the presence of H2S, with detection limits (LOD) of 3 μM for P–NO2 and 7 μM for ZnP–NO2. In the case of ZnP–NO2, the spectral shift enables a ratiometric sensing of H2S, making this approach particularly robust against variations in sensor concentration, environmental effects and instrumentation errors. Interestingly, the spectral changes induced by H2S were reversible suggesting that it is possible to reuse the sensor. The sensing mechanism was evaluated by 1H NMR and HRMS-ESI experiments and corroborated by density functional theory (DFT) calculations. Overall, the results emphasized that the β-nitroporphyrins based probes are a powerful tool for the detection of H2S and present potential as a new sensing approach.
{"title":"Optical detection of hydrogen sulfide by Turn-ON chemosensors based on 2-nitro-5,10,15,20-tetraphenylporphyrins","authors":"Carla I.M. Santos , Ana M. Santiago , Cristina J. Dias , Ana R. Araújo , Daniel Cavaco , Gonçalo Justino , Manuel Melle-Franco , M. Amparo F. Faustino , M. Graça P.M. S. Neves , JoséM.G. Martinho , Ermelinda M.S. Maçôas","doi":"10.1016/j.dyepig.2025.112801","DOIUrl":"10.1016/j.dyepig.2025.112801","url":null,"abstract":"<div><div>The sensing ability of 2-nitro-5,10,15,20-tetraphenylporphyrin <strong>(P–NO<sub>2</sub>)</strong> and of the corresponding Zn(II) complex <strong>(ZnP–NO<sub>2</sub>)</strong> towards hydrogen sulfide (H<sub>2</sub>S) was investigated using UV–vis absorption and emission spectroscopy. The presence of H<sub>2</sub>S induced strong alterations in the excited state of <strong>P–NO<sub>2</sub></strong> and <strong>ZnP–NO<sub>2</sub></strong>. Specifically, the originally broad fluorescence emission observed around 700 nm was strongly quenched, while new sharp bands emerged at lower wavelengths. Both <strong>P–NO<sub>2</sub></strong> and <strong>ZnP–NO<sub>2</sub></strong> showed a clear sensitive and turn-ON response to the presence of H<sub>2</sub>S, with detection limits (LOD) of 3 μM for <strong>P–NO<sub>2</sub></strong> and 7 μM for <strong>ZnP–NO<sub>2</sub></strong>. In the case of <strong>ZnP–NO<sub>2</sub></strong>, the spectral shift enables a ratiometric sensing of H<sub>2</sub>S, making this approach particularly robust against variations in sensor concentration, environmental effects and instrumentation errors. Interestingly, the spectral changes induced by H<sub>2</sub>S were reversible suggesting that it is possible to reuse the sensor. The sensing mechanism was evaluated by <sup>1</sup>H NMR and HRMS-ESI experiments and corroborated by density functional theory (DFT) calculations. Overall, the results emphasized that the β-nitroporphyrins based probes are a powerful tool for the detection of H<sub>2</sub>S and present potential as a new sensing approach.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112801"},"PeriodicalIF":4.1,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143869478","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}
The first phenothiazine (PT) imine polycatenar columnar mesogens consisting of a PT central core with 4′-substituted biphenylene-4-imino units at both wings and connecting with two terminal 2,4,5-trialkoxyphenyl groups via ester or ether links have been synthesized. These compounds self-assemble into hexagonal columnar liquid crystalline (LC) mesophases. They exhibit green to yellow fluorescence emission with large stokes shift in their LC, solution and solid states. They show aggregation-induced enhanced emission (AIEE) and mechanofluorochromic (MFC) behavior. The influences of ester or ether links on their properties have been discussed. Ether compound PT-E, with more planar conformation and higher electron density on the PT core, forms gel in an organic solution and shows stronger solid-state fluorescence emission, AIEE and MFC effects. The applications of PT-E as a chemosensor towards Al (III) and in white light emission diode (WLED) have been explored. In addition, using Caenorhabditis elegans as an animal model, the bioimaging of these fluorescence materials has been investigated. The results show that Caenorhabditis elegans (C. elegans) exhibits greater fluorescence in the PT-E solution.
{"title":"Polycatenar mesogens based on phenothiazine imine: Liquid crystal and photophysical properties","authors":"Yixian Li , Shibo Chen , Yuantang Duan , Zilong Guo , Wenyong Xiong , Hongmei Zhao , Xiaohong Cheng","doi":"10.1016/j.dyepig.2025.112817","DOIUrl":"10.1016/j.dyepig.2025.112817","url":null,"abstract":"<div><div>The first phenothiazine (PT) imine polycatenar columnar mesogens consisting of a PT central core with 4′-substituted biphenylene-4-imino units at both wings and connecting with two terminal 2,4,5-trialkoxyphenyl groups via ester or ether links have been synthesized. These compounds self-assemble into hexagonal columnar liquid crystalline (LC) mesophases. They exhibit green to yellow fluorescence emission with large stokes shift in their LC, solution and solid states. They show aggregation-induced enhanced emission (AIEE) and mechanofluorochromic (MFC) behavior. The influences of ester or ether links on their properties have been discussed. Ether compound <strong>PT-E,</strong> with more planar conformation and higher electron density on the PT core, forms gel in an organic solution and shows stronger solid-state fluorescence emission, AIEE and MFC effects. The applications of <strong>PT-E</strong> as a chemosensor towards Al (III) and in white light emission diode (WLED) have been explored. In addition, using <em>Caenorhabditis elegans</em> as an animal model, the bioimaging of these fluorescence materials has been investigated. The results show that <em>Caenorhabditis elegans (C. elegans)</em> exhibits greater fluorescence in the <strong>PT-E</strong> solution.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112817"},"PeriodicalIF":4.1,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143825679","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 : 2025-04-10DOI: 10.1016/j.dyepig.2025.112827
Marcia Domínguez , David Azorín-Soriano , Jessie García-Fleitas , Jennifer Soler-Beatty , Andrea Bernardos , Alba García-Fernández , Juan F. Blandez , Félix Sancenón , Ramón Martínez-Máñez
We report herein the design and synthesis of a near-infrared fluorescent probe (NB–SO3-Leu) derived from the Nile Blue (NB) fluorophore scaffold, modified with sulfonic groups to improve solubility and biocompatibility. The mechanism of action of the NB-SO3-Leu probe was successfully validated in the presence of leucine aminopeptidase (LAP), a widely known cancer biomarker. The fluorescence signal of NB-SO3-Leu, which was initially low, increased 4-fold after incubation with the LAP enzyme after 15 min. In addition, the NB-SO3-Leu probe was validated in vitro in 4T1 (mouse mammary carcinoma cells), HeLa (human cervical cancer cells), and SK-Mel-103 (human melanoma cells) with high endogenous LAP levels. This work aims to advance in the development of a new generation of reliable and sensitive cancer detection methods.
{"title":"Development of a novel near-infrared fluorescent probe based on nile blue for the detection of leucine aminopeptidase as a cancer biomarker","authors":"Marcia Domínguez , David Azorín-Soriano , Jessie García-Fleitas , Jennifer Soler-Beatty , Andrea Bernardos , Alba García-Fernández , Juan F. Blandez , Félix Sancenón , Ramón Martínez-Máñez","doi":"10.1016/j.dyepig.2025.112827","DOIUrl":"10.1016/j.dyepig.2025.112827","url":null,"abstract":"<div><div>We report herein the design and synthesis of a near-infrared fluorescent probe (<strong>NB–SO<sub>3</sub>-Leu</strong>) derived from the Nile Blue (NB) fluorophore scaffold, modified with sulfonic groups to improve solubility and biocompatibility. The mechanism of action of the <strong>NB-SO<sub>3</sub>-Leu</strong> probe was successfully validated in the presence of leucine aminopeptidase (LAP), a widely known cancer biomarker. The fluorescence signal of <strong>NB-SO<sub>3</sub>-Leu</strong>, which was initially low, increased 4-fold after incubation with the LAP enzyme after 15 min. In addition, the <strong>NB-SO<sub>3</sub>-Leu</strong> probe was validated <em>in vitro</em> in 4T1 (mouse mammary carcinoma cells), HeLa (human cervical cancer cells), and SK-Mel-103 (human melanoma cells) with high endogenous LAP levels. This work aims to advance in the development of a new generation of reliable and sensitive cancer detection methods.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112827"},"PeriodicalIF":4.1,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143828945","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 : 2025-04-10DOI: 10.1016/j.dyepig.2025.112822
Jingsheng Wang , Shiying Hu , Yuying Wu, Yaotian Zhang, Yeting Tao, Youtian Tao
The influence of heavy atom effects in organic host materials has been rarely explored in organic light-emitting diodes (OLEDs). In this study, we present four novel carbazole/oxadiazole hybrid bipolar transport host materials with heavy bromine atom substitution: the asymmetric Cz-3BrCzOXD and Cz-4BrCzOXD, and the symmetric o-3BrCzOXD and o-4BrCzOXD. By introducing one or two bromine atoms at the 3- or 4-position of the carbazole units, all brominated hosts exhibited similar energy levels, while demonstrating enhanced hole transport and a slight reduction in electron transport compared to the bromine-free control material, o-CzOXD. When doped with either phosphorescent or thermally activated delayed fluorescence (TADF) dopants, the brominated hosts demonstrated enhanced intersystem crossing (ISC) rates, leading to more efficient exciton utilization. Consequently, compared to o-CzOXD, both phosphorescent and TADF OLEDs exhibited improved device efficiencies for all four brominated hosts. The maximum external quantum efficiencies increased from 20.9 % to 24.3 % for green phosphorescent (ppy)2Ir(acac) OLEDs, from 20.3 % to 24.5 % for green TADF 4tCzDOXD OLEDs, and from 21.3 % to 24.9 % for light-blue TADF dCF35tCzOXD OLEDs. Our findings indicate that the external heavy atom effect offers an effective strategy for enhancing the efficiency of both phosphorescent and TADF OLEDs.
{"title":"External heavy atom effect in brominated carbazole/oxadiazole hybrid hosts for enhanced efficiency in phosphorescence and TADF OLEDs","authors":"Jingsheng Wang , Shiying Hu , Yuying Wu, Yaotian Zhang, Yeting Tao, Youtian Tao","doi":"10.1016/j.dyepig.2025.112822","DOIUrl":"10.1016/j.dyepig.2025.112822","url":null,"abstract":"<div><div>The influence of heavy atom effects in organic host materials has been rarely explored in organic light-emitting diodes (OLEDs). In this study, we present four novel carbazole/oxadiazole hybrid bipolar transport host materials with heavy bromine atom substitution: the asymmetric Cz-3BrCzOXD and Cz-4BrCzOXD, and the symmetric <em>o</em>-3BrCzOXD and <em>o</em>-4BrCzOXD. By introducing one or two bromine atoms at the 3- or 4-position of the carbazole units, all brominated hosts exhibited similar energy levels, while demonstrating enhanced hole transport and a slight reduction in electron transport compared to the bromine-free control material, <em>o</em>-CzOXD. When doped with either phosphorescent or thermally activated delayed fluorescence (TADF) dopants, the brominated hosts demonstrated enhanced intersystem crossing (ISC) rates, leading to more efficient exciton utilization. Consequently, compared to <em>o</em>-CzOXD, both phosphorescent and TADF OLEDs exhibited improved device efficiencies for all four brominated hosts. The maximum external quantum efficiencies increased from 20.9 % to 24.3 % for green phosphorescent (ppy)<sub>2</sub>Ir(acac) OLEDs, from 20.3 % to 24.5 % for green TADF 4tCzDOXD OLEDs, and from 21.3 % to 24.9 % for light-blue TADF dCF<sub>3</sub>5tCzOXD OLEDs. Our findings indicate that the external heavy atom effect offers an effective strategy for enhancing the efficiency of both phosphorescent and TADF OLEDs.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112822"},"PeriodicalIF":4.1,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143838913","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}
In this paper, two novel thioxanthene - phenothiazine derivatives (TPTZ1 and TPTZ2) were successfully synthesized based on phenothiazine and thiochromone. The structures of these two organic compounds were characterized by various spectroscopic techniques. The third order nonlinear optical (NLO) properties of TPTZ1 and TPTZ2 have been investigated by using the Z-scan technique under irradiance of 20ps pulse laser at 532 nm. It is discovered that TPTZ1 and TPTZ2 show the obvious reverse saturable absorption (RSA) characteristics and the typical saturable absorption (SA) characteristics, respectively. The nonlinear absorption coefficients (β) and nonlinear refractive indices (n2) of TPTZ1 and TPTZ2 are calculated to be the order of 10−11 m/W and 10−18 m2/W. The opposite nonlinear absorption behavior and the size difference of the nonlinear refraction indices may result from the differences in the electronic structure due to the different substituents for the two organic compounds. The figure-of-merit (FOM) of TPTZ2 is larger than that of TPTZ1 and even reaches 10.43 at the incident energy of 30 nJ. Their excellent NLO properties may allow them to be potentially applied in the photonic field.
{"title":"New thioxanthene - Phenothiazine derivatives:synthesis, characterization and third-order nonlinear optical (NLO) properties","authors":"Yunpeng Xu , Yuanyuan Wu , Xiaofan Chen , Chang Liu , Feng Wu , Xianshun Zeng","doi":"10.1016/j.dyepig.2025.112807","DOIUrl":"10.1016/j.dyepig.2025.112807","url":null,"abstract":"<div><div>In this paper, two novel thioxanthene - phenothiazine derivatives (<strong>TPTZ1</strong> and <strong>TPTZ2</strong>) were successfully synthesized based on phenothiazine and thiochromone. The structures of these two organic compounds were characterized by various spectroscopic techniques. The third order nonlinear optical (NLO) properties of <strong>TPTZ1</strong> and <strong>TPTZ2</strong> have been investigated by using the Z-scan technique under irradiance of 20ps pulse laser at 532 nm. It is discovered that <strong>TPTZ1</strong> and <strong>TPTZ2</strong> show the obvious reverse saturable absorption (RSA) characteristics and the typical saturable absorption (SA) characteristics, respectively. The nonlinear absorption coefficients (β) and nonlinear refractive indices (n<sub>2</sub>) of <strong>TPTZ1</strong> and <strong>TPTZ2</strong> are calculated to be the order of 10<sup>−11</sup> m/W and 10<sup>−18</sup> m<sup>2</sup>/W. The opposite nonlinear absorption behavior and the size difference of the nonlinear refraction indices may result from the differences in the electronic structure due to the different substituents for the two organic compounds. The figure-of-merit (FOM) of <strong>TPTZ2</strong> is larger than that of <strong>TPTZ1</strong> and even reaches 10.43 at the incident energy of 30 nJ. Their excellent NLO properties may allow them to be potentially applied in the photonic field.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"240 ","pages":"Article 112807"},"PeriodicalIF":4.1,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143828158","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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