Pub Date : 2026-01-16DOI: 10.1016/j.dyepig.2026.113582
Wenfeng Zhou , Haotian Jiang , Shiyu Wu , Kangyao Chen , Ning Ma , Hongchuan Wu , Yahui Zhang
Incorporation of fused ring structure can effectively redshift the wavelength of host-guest doped organic room temperature phosphorescent (ORTP) materials, but would cause inefficient intersystem crossing (ISC) due to the increased singlet-triplet energy gap. To address the issue, we proposed a fused ring-fused heterocyclic ring (FR-FHR) guest strategy to achieve outstanding ORTP. In this strategy, fused ring (FR) contributes to the long wavelength emission, and fused heterocyclic ring (FHR) is enhances the ISC, thus enabling the simultaneous realization of long wavelength emission and high signal-to-background ratio (SBR). Three guest molecules -NTPH, OTPH, and STPH- were designed and synthesized, each comprising two distinct building blocks: a fused ring core and a fused heterocyclic ring substituent. When doped into a Benzophenone (BPO) host, the resulting BPO/XTPHs system showed outstanding phosphorescence lifetime (from 0.276 to 0.343 s) and long afterglow performance (at least 6 s of afterglow emission), which leads a remarkable SBR as high as 4945 after UV off 30 s by in vivo imaging system imaging. The excellent time-dependent characteristics and high SBR of BPO/XTPH highlight their potential for practical applications in afterglow imaging, such as fingerprint visualization.
{"title":"High signal-to-background ratio based on guest-host doped organic room-temperature phosphorescent with a fused ring-fused heterocyclic ring strategy","authors":"Wenfeng Zhou , Haotian Jiang , Shiyu Wu , Kangyao Chen , Ning Ma , Hongchuan Wu , Yahui Zhang","doi":"10.1016/j.dyepig.2026.113582","DOIUrl":"10.1016/j.dyepig.2026.113582","url":null,"abstract":"<div><div>Incorporation of fused ring structure can effectively redshift the wavelength of host-guest doped organic room temperature phosphorescent (ORTP) materials, but would cause inefficient intersystem crossing (ISC) due to the increased singlet-triplet energy gap. To address the issue, we proposed a fused ring-fused heterocyclic ring (FR-FHR) guest strategy to achieve outstanding ORTP. In this strategy, fused ring (FR) contributes to the long wavelength emission, and fused heterocyclic ring (FHR) is enhances the ISC, thus enabling the simultaneous realization of long wavelength emission and high signal-to-background ratio (SBR). Three guest molecules -NTPH, OTPH, and STPH- were designed and synthesized, each comprising two distinct building blocks: a fused ring core and a fused heterocyclic ring substituent. When doped into a Benzophenone (BPO) host, the resulting BPO/XTPHs system showed outstanding phosphorescence lifetime (from 0.276 to 0.343 s) and long afterglow performance (at least 6 s of afterglow emission), which leads a remarkable SBR as high as 4945 after UV off 30 s by in vivo imaging system imaging. The excellent time-dependent characteristics and high SBR of BPO/XTPH highlight their potential for practical applications in afterglow imaging, such as fingerprint visualization.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"248 ","pages":"Article 113582"},"PeriodicalIF":4.2,"publicationDate":"2026-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146034384","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 : 2026-01-16DOI: 10.1016/j.dyepig.2026.113575
Peirong Zhou , Shuai Zhang , Yingying Meng , Kaizheng Liu , Xiaoran Huang , Jiaming Mao , Xianan Gao , Tongying Liang , Liang Yao , Hongwei Song , Congcong Cao , Cheng Zhou
Accurate and multiplexed biomarker detection requires probes that combine high brightness, spectral programmability, and biocompatibility. This work reports a fluorescence-encoding liposome platform based on membrane-intercalating conjugated oligoelectrolytes (MICOEs). Two water-soluble MICOE dyes, red-emissive ZBT and green-emissive ZBen, were designed to mimic phospholipids, enabling spontaneous insertion of their π-conjugated cores into lipid bilayers while exposing ionic end groups to water. Membrane intercalation confines and shields the chromophores, affording up to ∼540-fold fluorescence enhancement and excellent photostability without perturbing vesicle size or permeability, as verified by dynamic light scattering and calcein leakage assays. Curvature-controlled studies reveal that smaller, highly curved liposomes incorporate more dye and display higher brightness, identifying nanoscale curvature as a handle to tune signal output. A pre-addition loading strategy, in which MICOEs co-assemble with lipids, yields nearly quantitative labeling and approximately threefold higher emission than post-addition. The resulting MICOE–liposomes exhibit low cytotoxicity, efficiently stain extracellular vesicles, and, after carcinoembryonic antigen (CEA) antibody conjugation, selectively label A549 cancer cells in confocal and flow cytometry experiments. By varying the ZBT:ZBen ratio, robust and reproducible ratiometric red/green signatures are generated at the single-vesicle level, establishing a versatile, biocompatible encoding platform for high-throughput multiplexed biosensing and diagnostic applications.
{"title":"Fluorescent liposomes based on membrane-intercalating conjugated oligoelectrolytes for fluorescence encoding detection","authors":"Peirong Zhou , Shuai Zhang , Yingying Meng , Kaizheng Liu , Xiaoran Huang , Jiaming Mao , Xianan Gao , Tongying Liang , Liang Yao , Hongwei Song , Congcong Cao , Cheng Zhou","doi":"10.1016/j.dyepig.2026.113575","DOIUrl":"10.1016/j.dyepig.2026.113575","url":null,"abstract":"<div><div>Accurate and multiplexed biomarker detection requires probes that combine high brightness, spectral programmability, and biocompatibility. This work reports a fluorescence-encoding liposome platform based on membrane-intercalating conjugated oligoelectrolytes (MICOEs). Two water-soluble MICOE dyes, red-emissive <strong>ZBT</strong> and green-emissive <strong>ZBen</strong>, were designed to mimic phospholipids, enabling spontaneous insertion of their π-conjugated cores into lipid bilayers while exposing ionic end groups to water. Membrane intercalation confines and shields the chromophores, affording up to ∼540-fold fluorescence enhancement and excellent photostability without perturbing vesicle size or permeability, as verified by dynamic light scattering and calcein leakage assays. Curvature-controlled studies reveal that smaller, highly curved liposomes incorporate more dye and display higher brightness, identifying nanoscale curvature as a handle to tune signal output. A pre-addition loading strategy, in which MICOEs co-assemble with lipids, yields nearly quantitative labeling and approximately threefold higher emission than post-addition. The resulting MICOE–liposomes exhibit low cytotoxicity, efficiently stain extracellular vesicles, and, after carcinoembryonic antigen (CEA) antibody conjugation, selectively label A549 cancer cells in confocal and flow cytometry experiments. By varying the <strong>ZBT</strong>:<strong>ZBen</strong> ratio, robust and reproducible ratiometric red/green signatures are generated at the single-vesicle level, establishing a versatile, biocompatible encoding platform for high-throughput multiplexed biosensing and diagnostic applications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"248 ","pages":"Article 113575"},"PeriodicalIF":4.2,"publicationDate":"2026-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146034373","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 : 2026-01-14DOI: 10.1016/j.dyepig.2026.113569
Céu M. Sousa , Jerome Berthet , Paulo J. Coelho
New colorless lactone-fused naphthopyrans with amino substituents were prepared and their photochromic properties studied in solution and dispersed in an organic polymeric matrix. UV irradiation of these compounds leads to an immediate development of an intense blue color which fades in a few seconds in the dark, unlike the parent unfused naphthopyrans which show a much slower response to the variable UV light intensity.
{"title":"Fast blue-switching photochromic lactone-fused naphthopyrans","authors":"Céu M. Sousa , Jerome Berthet , Paulo J. Coelho","doi":"10.1016/j.dyepig.2026.113569","DOIUrl":"10.1016/j.dyepig.2026.113569","url":null,"abstract":"<div><div>New colorless lactone-fused naphthopyrans with amino substituents were prepared and their photochromic properties studied in solution and dispersed in an organic polymeric matrix. UV irradiation of these compounds leads to an immediate development of an intense blue color which fades in a few seconds in the dark, unlike the parent unfused naphthopyrans which show a much slower response to the variable UV light intensity.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"248 ","pages":"Article 113569"},"PeriodicalIF":4.2,"publicationDate":"2026-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145973453","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 : 2026-01-14DOI: 10.1016/j.dyepig.2026.113571
Dengchao Li , Qiumin Han , Yuxin Chen , Yanni Zhu , Ruifeng Mao
A novel fluorescent probe (TCF-MA) for highly selective detection of cysteine over homocysteine and glutathione was developed using TCF-NH2 as a fluorophore and maleimide as a recognition group, respectively. The structure of TCF-MA was characterized by 1H NMR, 13C NMR and HRMS spectroscopy, respectively. The results showed that the absorption peak of TCF-MA solution was at 400 nm, while adding cysteine to probe solution, fluorescent intensity was significant enhancement at 580 nm under excited wavelength of 440 nm with 140 nm Stokes shift. The probe exhibits high selectivity and sensitivity towards cysteine with a detection limit of 0.26 μM. The proposed response mechanism was validated by theoretical calculation and HPLC trace the reaction process. In addition, application of TCF-MA in test papers, SDS-PAGE and food samples were also investigated. Therefore, the probe can be a potential tool for highly detection of cysteine over homocysteine and glutathione in samples.
{"title":"A novel maleimide based fluorescent probe for highly selective detection of cysteine over homocysteine and glutathione and its application in test paper, protein staining and food samples","authors":"Dengchao Li , Qiumin Han , Yuxin Chen , Yanni Zhu , Ruifeng Mao","doi":"10.1016/j.dyepig.2026.113571","DOIUrl":"10.1016/j.dyepig.2026.113571","url":null,"abstract":"<div><div>A novel fluorescent probe (TCF-MA) for highly selective detection of cysteine over homocysteine and glutathione was developed using TCF-NH<sub>2</sub> as a fluorophore and maleimide as a recognition group, respectively. The structure of TCF-MA was characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS spectroscopy, respectively. The results showed that the absorption peak of TCF-MA solution was at 400 nm, while adding cysteine to probe solution, fluorescent intensity was significant enhancement at 580 nm under excited wavelength of 440 nm with 140 nm Stokes shift. The probe exhibits high selectivity and sensitivity towards cysteine with a detection limit of 0.26 μM. The proposed response mechanism was validated by theoretical calculation and HPLC trace the reaction process. In addition, application of TCF-MA in test papers, SDS-PAGE and food samples were also investigated. Therefore, the probe can be a potential tool for highly detection of cysteine over homocysteine and glutathione in samples.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"249 ","pages":"Article 113571"},"PeriodicalIF":4.2,"publicationDate":"2026-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146090495","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 : 2026-01-14DOI: 10.1016/j.dyepig.2026.113574
Xuteng Lang , Xin Meng , Xiaohan Zheng , Jian Tang , Ensheng Zhang , Yuanchun He , Xiaoxiang Zhang , Ziping Cao , X. Lang , X. Meng , X. Zheng , J. Tang , E. Zhang , Y. He , Z. Cao , Z. Zhang
Structural engineering is pivotal for modulating emission mechanisms in organic luminescent materials. By introducing twisted electron-donating groups and varying the modes of chiral scaffold incorporation, we present the synthesis and analysis of two novel luminophores, (S)-BiNpIm and (S,S)-EtBiNpIm. Photophysical studies reveal marked differences in emission wavelengths, a distinction attributable to fundamental variations in their emission pathways. Single-crystal X-ray diffraction and theoretical calculations provide compelling evidence for both through-bond charge transfer (TBCT) and through-space charge transfer (TSCT) processes. Notably, the spatially parallel arrangement of electron donors in (S,S)-EtBiNpIm interrupts conventional TBCT pathways, resulting in distinctive TSCT behavior. Both compounds display pronounced chiroptical activity in the excited state, as evidenced by circularly polarized luminescence measurements. Furthermore, these materials exhibit reversible, stimuli-responsive luminescence modulation upon acid-base treatment, highly sensitive acid detection in organic phases, and the capacity to serve as efficient emitters in LED devices. Collectively, these findings offer valuable insight into the fine-tuning of chiral luminescence via strategic molecular engineering of charge transfer processes, thereby advancing the development of responsive chiral materials for optoelectronic and sensing applications.
{"title":"Tuning charge transfer pathways through chiral binaphthyl structural engineering: Molecular design and versatile applications","authors":"Xuteng Lang , Xin Meng , Xiaohan Zheng , Jian Tang , Ensheng Zhang , Yuanchun He , Xiaoxiang Zhang , Ziping Cao , X. Lang , X. Meng , X. Zheng , J. Tang , E. Zhang , Y. He , Z. Cao , Z. Zhang","doi":"10.1016/j.dyepig.2026.113574","DOIUrl":"10.1016/j.dyepig.2026.113574","url":null,"abstract":"<div><div>Structural engineering is pivotal for modulating emission mechanisms in organic luminescent materials. By introducing twisted electron-donating groups and varying the modes of chiral scaffold incorporation, we present the synthesis and analysis of two novel luminophores, (<em>S</em>)-<strong>BiNpIm</strong> and (<em>S</em>,<em>S</em>)-<strong>EtBiNpIm</strong>. Photophysical studies reveal marked differences in emission wavelengths, a distinction attributable to fundamental variations in their emission pathways. Single-crystal X-ray diffraction and theoretical calculations provide compelling evidence for both through-bond charge transfer (TBCT) and through-space charge transfer (TSCT) processes. Notably, the spatially parallel arrangement of electron donors in (<em>S</em>,<em>S</em>)-<strong>EtBiNpIm</strong> interrupts conventional TBCT pathways, resulting in distinctive TSCT behavior. Both compounds display pronounced chiroptical activity in the excited state, as evidenced by circularly polarized luminescence measurements. Furthermore, these materials exhibit reversible, stimuli-responsive luminescence modulation upon acid-base treatment, highly sensitive acid detection in organic phases, and the capacity to serve as efficient emitters in LED devices. Collectively, these findings offer valuable insight into the fine-tuning of chiral luminescence via strategic molecular engineering of charge transfer processes, thereby advancing the development of responsive chiral materials for optoelectronic and sensing applications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"249 ","pages":"Article 113574"},"PeriodicalIF":4.2,"publicationDate":"2026-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146036635","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 : 2026-01-14DOI: 10.1016/j.dyepig.2026.113576
Long Fang , Qixin Zhou , Shujun Wang , Rui Wang , Liang Yin , Yaping Wang , Hanping He
Traditional fluoresceins have been widely employed in chemical and biological analyses owing to their high molar extinction coefficients, excellent fluorescence quantum yields, and low toxicity. However, their practical application in biological imaging is limited by a small Stokes shift, which arises from the symmetry of their molecular structures and results in a low signal-to-noise ratio as well as significant fluorescence self-quenching. In this work, a series of novel asymmetric carboxyl fluorescein derivatives were successfully synthesized by incorporating various thienyl heterocyclic rings in the fluorescein scaffold. Among these derivatives, Fam-T-Ph exhibited a remarkably large Stokes shift of up to 108 nm, along with a red-shifted wavelength (632 nm). Furthermore, immunofluorescence staining experiments confirmed that Fam-T-Ph possesses strong and reliable fluorescence imaging performance. These newly designed derivatives hold potential as fluorescent labeling agents for biological applications.
{"title":"A novel asymmetric fluorescein derivative with larger Stokes shift: design, synthesis and application in immunofluorescence tissue staining","authors":"Long Fang , Qixin Zhou , Shujun Wang , Rui Wang , Liang Yin , Yaping Wang , Hanping He","doi":"10.1016/j.dyepig.2026.113576","DOIUrl":"10.1016/j.dyepig.2026.113576","url":null,"abstract":"<div><div>Traditional fluoresceins have been widely employed in chemical and biological analyses owing to their high molar extinction coefficients, excellent fluorescence quantum yields, and low toxicity. However, their practical application in biological imaging is limited by a small Stokes shift, which arises from the symmetry of their molecular structures and results in a low signal-to-noise ratio as well as significant fluorescence self-quenching. In this work, a series of novel asymmetric carboxyl fluorescein derivatives were successfully synthesized by incorporating various thienyl heterocyclic rings in the fluorescein scaffold. Among these derivatives, <strong>Fam-T-Ph</strong> exhibited a remarkably large Stokes shift of up to 108 nm, along with a red-shifted wavelength (632 nm). Furthermore, immunofluorescence staining experiments confirmed that <strong>Fam-T-Ph</strong> possesses strong and reliable fluorescence imaging performance. These newly designed derivatives hold potential as fluorescent labeling agents for biological applications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"248 ","pages":"Article 113576"},"PeriodicalIF":4.2,"publicationDate":"2026-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145973451","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}
Aquilegia buergeriana var. oxysepala and A. flabellata var. pumila are two commonly found Aquilegia species in Japan. To clarify the chemical differences underlying the sepal color difference between the two species, we investigated the pigments in their flowers. A total of seven previously undescribed compounds were isolated from the flowers of A. buergeriana var. oxysepala and A. flabellata var. pumila. One previously undescribed anthocyanin, delphinidin 3-O-(3″-malonylglucopyranoside), together with three known delphinidin glucosides, was isolated and identified from A. buergeriana var. oxysepala, while six previously undescribed compounds were isolated and identified from A. flabellata var. pumila. These included four delphinidin glycosides, one flavonol glycoside, and one C-glycosyl flavone; specifically, delphinidin 3-O-glucopyranoside-7-O-(6″-E-caffeoylglucopyranoside), delphinidin 3-O-(6″-E-caffeoylglucopyranoside)-7-O-(6‴-E-caffeoylglucopyranoside), delphinidin 3-O-(3″,6″-E-dicaffeoylglucopyranoside)-7-O-(6‴-E-caffeoylglucopyranoside), delphinidin 3-O-[3″-O-(1⁗-E-caffeoylglucopyranosyl)-(6→3)-malonyl-(6″-malonylglucopyranoside)-7-O-(6‴-E-caffeoylglucopyranoside), quercetin 3-O-glucopyranoside-7-O-[6''-(4‴-O-glucopyranosyl-E-p-coumaroyl)-glucopyranoside], and luteolin 6-C-[6''-(4‴-O-glucopyranosyl-E-p-coumaroyl)-glucopyranoside]. Seven known phenolics were also found in the flowers of A. flabellata var. pumila.
The pH of the sepals and petals of both species ranged from 5.6 to 5.8. In vitro sepal color reconstruction experiments showed that the sepal colors of A. buergeriana var. oxysepala and A. flabellata var. pumila could be attributed to their respective major anthocyanins. The violet coloration of A. flabellata var. pumila sepals is primarily due to intramolecular copigmentation rather than intermolecular effects. The main structural difference between these anthocyanins is that those of A. flabellata var. pumila possess a 6-caffeoylglucoside moiety at the 7-position, whereas those of A. buergeriana var. oxysepala do not. Our findings suggest that 7-O-glycosylation and acylation of delphinidin may play an important role in the formation of blue hue in the flower.
黄貂鱼是日本常见的两种黄貂鱼。为了弄清这两种植物萼片颜色差异背后的化学差异，我们研究了它们花中的色素。共分离到7个以前未见过的化合物，这些化合物分别来自布氏花和黄斑花。分离鉴定了一种先前未被描述的花青素，即飞燕苷3- o -（3″-丙二酰葡萄糖吡喃苷）和三种已知的飞燕苷糖苷类化合物，并从黄翅飞燕中分离鉴定了六种先前未被描述的化合物。其中包括四种飞燕苷苷、一种黄酮醇苷和一种c -糖基黄酮；具体来说，是delphi苷3- o -glucopyranoside-7- o -(6″- e- caffeoylglucopyranoside)， delphi苷3- o -(6″- e- caffeoylglucopyranoside)-7- o -(6″- e- caffeoylglucopyranoside)， delphi苷3- o -(3″，6″- e- dicaffeoylglucopyranoside)-7- o -(6″- e- caffeoylglucopyranoside)， delphi苷3- o -[3″- o -(1⁗- e- caffeoylglucopyranoside)-(6 -″- e- caffeoylglucopyranoside)-(6 -″- e- caffeoylglucopyranoside)]，槲皮素3- o -glucopyranoside-7- o -[6”-(4 - o -glucopyranoside- e- p-coumaroyl)-glucopyranoside]，木犀草素6- c -[6′-(4′- o - glucopyranoyl - e -p-coumaroyl)- glucopyrano苷]。此外，还在黄柳花中发现了7种已知的酚类物质。两种植物萼片和花瓣的pH值均在5.6 ~ 5.8之间。离体萼片颜色重建实验表明，布氏蜂属和黄斑蜂属的萼片颜色可能与它们各自的主要花青素有关。黄翅草萼片的紫色主要是由于分子内的共色素作用，而不是分子间的作用。这两种花青素在结构上的主要区别是，黄叶菊变种花青素在7位上含有6-咖啡基糖苷，而黄叶菊变种花青素在7位上没有。我们的研究结果表明，飞燕草苷的7- o糖基化和酰化可能在花的蓝色色调形成中起重要作用。
{"title":"Acylated delphinidin glycosides from red-purple sepals of Aquilegia buergeriana var. oxysepala and violet sepals of A. flabellata var. pumila (Ranunculaceae)","authors":"Qi Qin , Kohtaro Sugahara , Takahisa Nakane , Kazushige Honda , Fumi Tatsuzawa , Tsukasa Iwashina , Takayuki Mizuno","doi":"10.1016/j.dyepig.2026.113567","DOIUrl":"10.1016/j.dyepig.2026.113567","url":null,"abstract":"<div><div><em>Aquilegia buergeriana</em> var. <em>oxysepala</em> and <em>A. flabellata</em> var. <em>pumila</em> are two commonly found <em>Aquilegia</em> species in Japan. To clarify the chemical differences underlying the sepal color difference between the two species, we investigated the pigments in their flowers. A total of seven previously undescribed compounds were isolated from the flowers of <em>A. buergeriana</em> var. <em>oxysepala</em> and <em>A. flabellata</em> var. <em>pumila</em>. One previously undescribed anthocyanin, delphinidin 3-<em>O</em>-(3″-malonylglucopyranoside), together with three known delphinidin glucosides, was isolated and identified from <em>A. buergeriana</em> var. <em>oxysepala</em>, while six previously undescribed compounds were isolated and identified from <em>A. flabellata</em> var. <em>pumila</em>. These included four delphinidin glycosides, one flavonol glycoside, and one <em>C</em>-glycosyl flavone; specifically, delphinidin 3-<em>O</em>-glucopyranoside-7-<em>O</em>-(6″-<em>E</em>-caffeoylglucopyranoside), delphinidin 3-<em>O</em>-(6″-<em>E</em>-caffeoylglucopyranoside)-7-<em>O</em>-(6‴-<em>E</em>-caffeoylglucopyranoside), delphinidin 3-<em>O</em>-(3″,6″-<em>E</em>-dicaffeoylglucopyranoside)-7-<em>O</em>-(6‴-<em>E</em>-caffeoylglucopyranoside), delphinidin 3-<em>O</em>-[3″-<em>O</em>-(1⁗-<em>E</em>-caffeoylglucopyranosyl)-(6→3)-malonyl-(6″-malonylglucopyranoside)-7-<em>O</em>-(6‴-<em>E</em>-caffeoylglucopyranoside), quercetin 3-<em>O</em>-glucopyranoside-7-<em>O</em>-[6''-(4‴-<em>O</em>-glucopyranosyl-<em>E</em>-<em>p</em>-coumaroyl)-glucopyranoside], and luteolin 6-<em>C</em>-[6''-(4‴-<em>O</em>-glucopyranosyl-<em>E</em>-<em>p</em>-coumaroyl)-glucopyranoside]. Seven known phenolics were also found in the flowers of <em>A. flabellata</em> var. <em>pumila</em>.</div><div>The pH of the sepals and petals of both species ranged from 5.6 to 5.8. <em>In vitro</em> sepal color reconstruction experiments showed that the sepal colors of <em>A. buergeriana</em> var. <em>oxysepala</em> and <em>A. flabellata</em> var. <em>pumila</em> could be attributed to their respective major anthocyanins. The violet coloration of <em>A. flabellata</em> var. <em>pumila</em> sepals is primarily due to intramolecular copigmentation rather than intermolecular effects. The main structural difference between these anthocyanins is that those of <em>A. flabellata</em> var. <em>pumila</em> possess a 6-caffeoylglucoside moiety at the 7-position, whereas those of <em>A. buergeriana</em> var. <em>oxysepala</em> do not. Our findings suggest that 7-<em>O</em>-glycosylation and acylation of delphinidin may play an important role in the formation of blue hue in the flower.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"249 ","pages":"Article 113567"},"PeriodicalIF":4.2,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146036581","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 : 2026-01-13DOI: 10.1016/j.dyepig.2026.113573
Xin Cong , Kaide Ou , Xuelin Dong , Yonggui Liao , Yajiang Yang , Hong Wang
The development of fluorescent materials capable of orthogonal and dynamic multicolor switching under multiple stimuli remains a significant challenge. A promising strategy is the spatial integration of independent responsive units. Herein, we report a bilayer film system engineered from a photo-responsive unit and a thermoresponsive unit. In this bilayer design, the top photo-responsive layer was created by loading photoresponsive unit into a poly (vinyl alcohol) (PVA) matrix. The photoresponsive unit was prepared by combining Eu3+-terpyridine complex with 1,2-bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene (DTE) and adenosine 5′-monophosphate. Due to fluorescence resonance energy transfer between Eu3+ and the photochromic DTE, the top layer exhibits reversible red-emission switching under UV/visible irradiation. The bottom thermo-responsive layer was prepared by dispersing 9,10-bis(phenylethynyl)anthracene (BPEA) and a phase-change material (PCM) within PVA, where the green fluorescence of BPEA is sharply modulated by the solid-liquid phase transition of the PCM via reversible aggregation control. The resulting bilayer BE/PVA film displays four distinct fluorescence colors (orange, bright green, dark red, and dark green) through orthogonal photo- and thermal-stimulation, benefiting from both independent stimulus responses and color overlay between the two layers. The film shows rapid response and good reversibility. Furthermore, we developed a Python-assisted RGB-quantization method that converts the film's dynamic multicolor fluorescence into quaternary codes. This approach enables the construction of information arrays based on BE/PVA films, significantly enhancing encryption security and data capacity. This work provides a general strategy for designing high-security, high-capacity encryption materials through orthogonal stimulus control and intelligent data processing.
{"title":"Stimuli-responsive multicolor fluorescent bilayer film for high-security encryption based on FRET and phase-change modulated emission","authors":"Xin Cong , Kaide Ou , Xuelin Dong , Yonggui Liao , Yajiang Yang , Hong Wang","doi":"10.1016/j.dyepig.2026.113573","DOIUrl":"10.1016/j.dyepig.2026.113573","url":null,"abstract":"<div><div>The development of fluorescent materials capable of orthogonal and dynamic multicolor switching under multiple stimuli remains a significant challenge. A promising strategy is the spatial integration of independent responsive units. Herein, we report a bilayer film system engineered from a photo-responsive unit and a thermoresponsive unit. In this bilayer design, the top photo-responsive layer was created by loading photoresponsive unit into a poly (vinyl alcohol) (PVA) matrix. The photoresponsive unit was prepared by combining Eu<sup>3+</sup>-terpyridine complex with 1,2-bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene (DTE) and adenosine 5′-monophosphate. Due to fluorescence resonance energy transfer between Eu<sup>3+</sup> and the photochromic DTE, the top layer exhibits reversible red-emission switching under UV/visible irradiation. The bottom thermo-responsive layer was prepared by dispersing 9,10-bis(phenylethynyl)anthracene (BPEA) and a phase-change material (PCM) within PVA, where the green fluorescence of BPEA is sharply modulated by the solid-liquid phase transition of the PCM via reversible aggregation control. The resulting bilayer BE/PVA film displays four distinct fluorescence colors (orange, bright green, dark red, and dark green) through orthogonal photo- and thermal-stimulation, benefiting from both independent stimulus responses and color overlay between the two layers. The film shows rapid response and good reversibility. Furthermore, we developed a Python-assisted RGB-quantization method that converts the film's dynamic multicolor fluorescence into quaternary codes. This approach enables the construction of information arrays based on BE/PVA films, significantly enhancing encryption security and data capacity. This work provides a general strategy for designing high-security, high-capacity encryption materials through orthogonal stimulus control and intelligent data processing.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"248 ","pages":"Article 113573"},"PeriodicalIF":4.2,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145973450","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 : 2026-01-12DOI: 10.1016/j.dyepig.2026.113570
Yuchen Deng , Bin Li , Wei Qi , Wei Liu , Ning Zhang , Lanlan Zhao , Huanrong Li
The rapid development of smart hydrogels has greatly increased the demand for systems with adaptive and multi-responsive capabilities. However, it remains challenging to integrate multiple responsive functions into a singular hydrogel network, as most systems lack the molecular design to enable synergistic and reversible control over these distinct properties. Herein, we present a novel multifunctional hydrogel based on a dynamic Eu3+ coordination complex with allyl modified pyridine-2,6-dicarboxylic acid (APDA). This material exhibits luminescence switching, tunable mechanical performance and shape memory behavior in response to acid/base stimuli. The dynamic lanthanide metal-ligand coordination allows the reversible assembly and disassembly of the hydrogel network in response to base/acid stimuli, so that the hydrogel can realize the reversible stiff-soft conversion. The Eu3+-APDA coordination complexes formed under basic conditions function dually as a luminescent center and a cross-linking bond, fixing the hydrogel's temporary shape. Conversely, acid stimulation triggers their disintegration, leading to simultaneous luminescence quenching and shape recovery. This intelligent hydrogel system provides a novel design strategy for stimuli-responsive, multi-functional luminescence soft materials.
{"title":"A multi-responsive hydrogel with luminescence switching, mechanical tuning, and shape memory via reversible Ln-coordination bonds","authors":"Yuchen Deng , Bin Li , Wei Qi , Wei Liu , Ning Zhang , Lanlan Zhao , Huanrong Li","doi":"10.1016/j.dyepig.2026.113570","DOIUrl":"10.1016/j.dyepig.2026.113570","url":null,"abstract":"<div><div>The rapid development of smart hydrogels has greatly increased the demand for systems with adaptive and multi-responsive capabilities. However, it remains challenging to integrate multiple responsive functions into a singular hydrogel network, as most systems lack the molecular design to enable synergistic and reversible control over these distinct properties. Herein, we present a novel multifunctional hydrogel based on a dynamic Eu<sup>3+</sup> coordination complex with allyl modified pyridine-2,6-dicarboxylic acid (APDA). This material exhibits luminescence switching, tunable mechanical performance and shape memory behavior in response to acid/base stimuli. The dynamic lanthanide metal-ligand coordination allows the reversible assembly and disassembly of the hydrogel network in response to base/acid stimuli, so that the hydrogel can realize the reversible stiff-soft conversion. The Eu<sup>3+</sup>-APDA coordination complexes formed under basic conditions function dually as a luminescent center and a cross-linking bond, fixing the hydrogel's temporary shape. Conversely, acid stimulation triggers their disintegration, leading to simultaneous luminescence quenching and shape recovery. This intelligent hydrogel system provides a novel design strategy for stimuli-responsive, multi-functional luminescence soft materials.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"248 ","pages":"Article 113570"},"PeriodicalIF":4.2,"publicationDate":"2026-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145973449","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 : 2026-01-12DOI: 10.1016/j.dyepig.2026.113560
Hong Chen , Yihan Yang , Pengwen Luo , Xiaoxia Cheng , Bin Hu , Wei Huang
A near-infrared (NIR) fluorescent probe (CCH) constructed from a chromenylium-cyanine scaffold was developed by integrating 4-diethylaminosalicylic acid as the structural unit and mercaptoazaheterocyclic compounds as functional modifiers. The probe exhibited high selectivity for Hg2+ detection in aqueous solutions and environmental samples across a broad pH range (2–10), with a rapid response time, enabling real-time monitoring of Hg2+ in aquatic environments. Spectral analyses showed a 1:1 binding ratio between CCH and Hg2+, with the detection limits of 3.20 × 10−7 M (Ultraviolet–Visible) and 1.22 × 10−7 M (fluorescence), along with a binding constant of 1.36 × 104 M−1. Mechanistic studies via mass spectrometry (MS), Fourier transform infrared spectroscopy (FTIR), and density functional theory (DFT) calculations confirmed a photoinduced electron transfer (PET)-based recognition mechanism. Practical applications validated the probe's effectiveness in environmental water analysis, filter paper-based assays, and food sample testing. Moreover, CCH exhibited excellent biocompatibility and successfully achieved the fluorescence imaging in cancer cells, underscoring its potential for biological applications.
{"title":"A thiolated N-heterocyclic modified chromenylium-cyanine-based NIR turn-on fluorescent probe for Hg2+ detection in environment and living cells","authors":"Hong Chen , Yihan Yang , Pengwen Luo , Xiaoxia Cheng , Bin Hu , Wei Huang","doi":"10.1016/j.dyepig.2026.113560","DOIUrl":"10.1016/j.dyepig.2026.113560","url":null,"abstract":"<div><div>A near-infrared (NIR) fluorescent probe (<strong>CCH</strong>) constructed from a chromenylium-cyanine scaffold was developed by integrating 4-diethylaminosalicylic acid as the structural unit and mercaptoazaheterocyclic compounds as functional modifiers. The probe exhibited high selectivity for Hg<sup>2+</sup> detection in aqueous solutions and environmental samples across a broad pH range (2–10), with a rapid response time, enabling real-time monitoring of Hg<sup>2+</sup> in aquatic environments. Spectral analyses showed a 1:1 binding ratio between <strong>CCH</strong> and Hg<sup>2+</sup>, with the detection limits of 3.20 × 10<sup>−7</sup> M (Ultraviolet–Visible) and 1.22 × 10<sup>−7</sup> M (fluorescence), along with a binding constant of 1.36 × 10<sup>4</sup> M<sup>−1</sup>. Mechanistic studies via mass spectrometry (MS), Fourier transform infrared spectroscopy (FTIR), and density functional theory (DFT) calculations confirmed a photoinduced electron transfer (PET)-based recognition mechanism. Practical applications validated the probe's effectiveness in environmental water analysis, filter paper-based assays, and food sample testing. Moreover, <strong>CCH</strong> exhibited excellent biocompatibility and successfully achieved the fluorescence imaging in cancer cells, underscoring its potential for biological applications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"248 ","pages":"Article 113560"},"PeriodicalIF":4.2,"publicationDate":"2026-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145973512","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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