Dyes and Pigments最新文献

英文中文

Effect of proton acceptors on the excited-state intermolecular proton transfer reaction of fluoranthene–urea compounds

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-15 DOI: 10.1016/j.dyepig.2025.112763

Tatsuki Hoshino, Mahiro Okada, Yoshinobu Nishimura

To investigate the effect of proton acceptors on the excited-state intermolecular proton transfer (ESPT) reaction of fluoranthene–urea compounds, three fluoranthene–urea compounds with different substituents were prepared. Photoexcitation of complexes composed of these compounds and proton acceptors in the ground state produced a normal form (N∗), and subsequent ESPT generated a tautomer form (T∗). Spectroscopic measurements of these complexes in the presence of tetrabutylammonium acetate (TBAAc) as a source of CH₃COO⁻ and tetrabutylammonium phosphate (TBAP) as a H₂PO₄⁻ source were performed. ¹H NMR spectra showed that the 1-(fluoranthene-3-yl)-3-phenylurea (3FU) derivatives formed complexes with CH₃COO⁻ and H₂PO₄⁻ in the ground state through hydrogen bonding interactions. Time-resolved fluorescence spectra showed that the maximum fluorescence wavelength of the T∗ species containing CH₃COO⁻ did not change with time, whereas that of the T∗ species containing H₂PO₄⁻ shifted to a longer wavelength. These results indicated that in the excited state, the structure of T∗ with H₂PO₄⁻ might be different from that of T∗ with CH₃COO⁻. Furthermore, the distribution of electron density of T∗ might be delocalized from the fluorescent moiety to the proton acceptor rather than being localized on the fluorescent moiety.

{"title":"Effect of proton acceptors on the excited-state intermolecular proton transfer reaction of fluoranthene–urea compounds","authors":"Tatsuki Hoshino, Mahiro Okada, Yoshinobu Nishimura","doi":"10.1016/j.dyepig.2025.112763","DOIUrl":"10.1016/j.dyepig.2025.112763","url":null,"abstract":"<div><div>To investigate the effect of proton acceptors on the excited-state intermolecular proton transfer (ESPT) reaction of fluoranthene–urea compounds, three fluoranthene–urea compounds with different substituents were prepared. Photoexcitation of complexes composed of these compounds and proton acceptors in the ground state produced a normal form (N∗), and subsequent ESPT generated a tautomer form (T∗). Spectroscopic measurements of these complexes in the presence of tetrabutylammonium acetate (TBAAc) as a source of CH3COO− and tetrabutylammonium phosphate (TBAP) as a H2PO4− source were performed. 1H NMR spectra showed that the 1-(fluoranthene-3-yl)-3-phenylurea (3FU) derivatives formed complexes with CH3COO− and H2PO4− in the ground state through hydrogen bonding interactions. Time-resolved fluorescence spectra showed that the maximum fluorescence wavelength of the T∗ species containing CH3COO− did not change with time, whereas that of the T∗ species containing H2PO4− shifted to a longer wavelength. These results indicated that in the excited state, the structure of T∗ with H2PO4− might be different from that of T∗ with CH3COO−. Furthermore, the distribution of electron density of T∗ might be delocalized from the fluorescent moiety to the proton acceptor rather than being localized on the fluorescent moiety.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112763"},"PeriodicalIF":4.1,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644256","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis, crystal structure, and sensing properties for Fe3+, Al3+, Cu2+, MnO4−, Cr2O72− and p-nitroaniline based on a 2D Cd coordination polymer

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-15 DOI: 10.1016/j.dyepig.2025.112764

Zan Sun , Yinong Liang , Yarong Xu , Kaixin Zhang

A two dimension Cd coordination polymer, namely [Cd(CPPCA) (H₂O)₂]_n (Cd-CPPCA, H₂CPPCA = 1-(4-carbxoylphenyl)piperidine-4-caboylic acid) has been synthesized under a simple one-step solvothermal process. Cd-CPPCA crystallizes in monoclinic crystal system P2₁/c space group with a = 14.1188 (6) Å, b = 7.7599 (4) Å, c = 12.7353 (6) Å and β = 93.505 (4) °. Cd-CPPCA adopts a 2-nodal 2D net with a schläfli symbol of {8⁴.12²}{8}₂. The 3D supramolecular structure of Cd-CPPCA was constructed via hydrogen bond (O–H⋯O) and π···π interaction between adjacent layers. As a promising sensing material, Cd-CPPCA exhibit excellent sensing ability for Fe³⁺, Cu²⁺, Al³⁺, MnO₄⁻, Cr₂O₇²⁻, p-nitroaniline (p-NA) with highly sensitivity, excellent recyclability and lower detection limits. The possible sensing mechanism was also discussed.

{"title":"Synthesis, crystal structure, and sensing properties for Fe3+, Al3+, Cu2+, MnO4−, Cr2O72− and p-nitroaniline based on a 2D Cd coordination polymer","authors":"Zan Sun , Yinong Liang , Yarong Xu , Kaixin Zhang","doi":"10.1016/j.dyepig.2025.112764","DOIUrl":"10.1016/j.dyepig.2025.112764","url":null,"abstract":"<div><div>A two dimension Cd coordination polymer, namely [Cd(CPPCA) (H2O)2]n (Cd-CPPCA, H2CPPCA = 1-(4-carbxoylphenyl)piperidine-4-caboylic acid) has been synthesized under a simple one-step solvothermal process. Cd-CPPCA crystallizes in monoclinic crystal system P21/c space group with a = 14.1188 (6) Å, b = 7.7599 (4) Å, c = 12.7353 (6) Å and β = 93.505 (4) °. Cd-CPPCA adopts a 2-nodal 2D net with a schläfli symbol of {84.122}{8}2. The 3D supramolecular structure of Cd-CPPCA was constructed via hydrogen bond (O–H⋯O) and π···π interaction between adjacent layers. As a promising sensing material, Cd-CPPCA exhibit excellent sensing ability for Fe3+, Cu2+, Al3+, MnO4−, Cr2O72−, p-nitroaniline (p-NA) with highly sensitivity, excellent recyclability and lower detection limits. The possible sensing mechanism was also discussed.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112764"},"PeriodicalIF":4.1,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644255","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Colorimetric recognition and adsorption of 1,4-benzoquinone using amine-functionalized polyacrylonitrile fibers

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-14 DOI: 10.1016/j.dyepig.2025.112768

Xuehua Zhang , Haocheng Sun , Xiaoting Li , Jian Cao , Ning Ma , Minli Tao , Wenqin Zhang

Various amine-functionalized polyacrylonitrile fibers (PAN_EF, PAN_PF, PAN_BF, PAN_NPF, and PAN_DNPF) were prepared and employed to detect and adsorb 1,4-benzoquinone. After comparing the different types of amines and different carbon chain lengths, the most evident color change was observed in PAN_NPF. This material possessed a suitable carbon chain length, strong alkalinity, and an adsorption capacity of up to 1.32 mol mol⁻¹. Following its immersion in a 1,4-benzoquinone solution for 30 s, PAN_NPF rapidly changed from yellow to dark brown. This interaction between amine and 1,4-benzoquinone was quick, rendering this approach effective for real-time monitoring. Moreover, PAN_NPF was highly effective in detecting 1,4-benzoquinone in water across a wide pH range (3–10), with a detection limit as low as 0.5 ppm. PAN_NPF maintained its sensitivity and underwent stable color changes even at low temperatures (0 °C), and the presence of ions and compounds in practical applications did not interfere with its discoloration behavior. The kinetic and isotherm curves revealed that the adsorption process was consistent with the Langmuir isothermal adsorption and pseudo-second-order kinetic models, demonstrating the chemical adsorption of 1,4-benzoquinone by PAN_NPF. These findings highlight the superior detection capabilities of PAN_NPF, rendering it an efficient and reliable material for environmental monitoring and water purification.

{"title":"Colorimetric recognition and adsorption of 1,4-benzoquinone using amine-functionalized polyacrylonitrile fibers","authors":"Xuehua Zhang , Haocheng Sun , Xiaoting Li , Jian Cao , Ning Ma , Minli Tao , Wenqin Zhang","doi":"10.1016/j.dyepig.2025.112768","DOIUrl":"10.1016/j.dyepig.2025.112768","url":null,"abstract":"<div><div>Various amine-functionalized polyacrylonitrile fibers (PANEF, PANPF, PANBF, PANNPF, and PANDNPF) were prepared and employed to detect and adsorb 1,4-benzoquinone. After comparing the different types of amines and different carbon chain lengths, the most evident color change was observed in PANNPF. This material possessed a suitable carbon chain length, strong alkalinity, and an adsorption capacity of up to 1.32 mol mol−1. Following its immersion in a 1,4-benzoquinone solution for 30 s, PANNPF rapidly changed from yellow to dark brown. This interaction between amine and 1,4-benzoquinone was quick, rendering this approach effective for real-time monitoring. Moreover, PANNPF was highly effective in detecting 1,4-benzoquinone in water across a wide pH range (3–10), with a detection limit as low as 0.5 ppm. PANNPF maintained its sensitivity and underwent stable color changes even at low temperatures (0 °C), and the presence of ions and compounds in practical applications did not interfere with its discoloration behavior. The kinetic and isotherm curves revealed that the adsorption process was consistent with the Langmuir isothermal adsorption and pseudo-second-order kinetic models, demonstrating the chemical adsorption of 1,4-benzoquinone by PANNPF. These findings highlight the superior detection capabilities of PANNPF, rendering it an efficient and reliable material for environmental monitoring and water purification.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112768"},"PeriodicalIF":4.1,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644254","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Modification of perylene red pigments with graphene oxide

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-13 DOI: 10.1016/j.dyepig.2025.112758

Dongjun Lv , Furui Jia , Xiaolei Zhang , Chenwei Qu , Ying Xu , Qiuya Li , Yuexing Zhang , Lingyun Cao

This study employed monolayer graphene oxide to modify the surface of perylene pigments C.I. Pigment Red 179 and C.I. Pigment Red 149 via ball milling in a solvent medium, aiming to improve their performance. The composition and structure of modified pigments were determined and characterized with scanning electron microscopy (SEM), X-ray powder diffraction (XRD), and X-ray photoelectron spectroscopy (XPS), and their fluorescence properties, specific surface area, thermal stability, particle size distribution, color characteristics, water contact angle, and dispersion stability were assessed. In addition, the adsorption structure and electronic properties of graphene oxide on the surface of perylene red pigment molecules, as well as the interaction behavior of perylene red pigment molecules with graphene oxide, were explained by density functional theory (DFT) calculations. Results showed non-covalent interactions between perylene red pigments and monolayer graphene oxide, leading to a more concentrated particle size distribution, enhanced yellow hue, and increased color strength to 104.3 %–117.1 %. The interaction distance between the two components was approximately 3.6 Å.

{"title":"Modification of perylene red pigments with graphene oxide","authors":"Dongjun Lv , Furui Jia , Xiaolei Zhang , Chenwei Qu , Ying Xu , Qiuya Li , Yuexing Zhang , Lingyun Cao","doi":"10.1016/j.dyepig.2025.112758","DOIUrl":"10.1016/j.dyepig.2025.112758","url":null,"abstract":"<div><div>This study employed monolayer graphene oxide to modify the surface of perylene pigments C.I. Pigment Red 179 and C.I. Pigment Red 149 via ball milling in a solvent medium, aiming to improve their performance. The composition and structure of modified pigments were determined and characterized with scanning electron microscopy (SEM), X-ray powder diffraction (XRD), and X-ray photoelectron spectroscopy (XPS), and their fluorescence properties, specific surface area, thermal stability, particle size distribution, color characteristics, water contact angle, and dispersion stability were assessed. In addition, the adsorption structure and electronic properties of graphene oxide on the surface of perylene red pigment molecules, as well as the interaction behavior of perylene red pigment molecules with graphene oxide, were explained by density functional theory (DFT) calculations. Results showed non-covalent interactions between perylene red pigments and monolayer graphene oxide, leading to a more concentrated particle size distribution, enhanced yellow hue, and increased color strength to 104.3 %–117.1 %. The interaction distance between the two components was approximately 3.6 Å.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112758"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143637617","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

19F NMR-based lithium sensors using 19F-Labeled aza-crown ethers: Regioisomeric and substituent effects

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-13 DOI: 10.1016/j.dyepig.2025.112762

Donghyeon Lee , Yanchuan Zhao , Byungjin Koo

We herein report ¹⁹F NMR-based molecular lithium sensors using ¹⁹F-labeled aza-crown ether derivatives and investigate the regioisomeric and substituent effects on ¹⁹F NMR lithium sensing. Four new fluorinated 1-aza-12-crown-4 derivatives were successfully synthesized via Buchwald-Hartwig amination. Fluorine substitution at the para position relative to the 1-aza-12-crown-4 moiety resulted in a 20-fold increase in chemical shift differences upon exposure to lithium ions, compared to the meta position. We also found that an electron-withdrawing nitro group on the fluorobenzene aza-crown ether prevented any ¹⁹F NMR chemical shifts upon exposure to lithium ions. In contrast, a methyl substituent at the same position as the nitro group induced remarkable (∼20 fold) chemical shifts, similar to the compound without any functional group. In addition, magnesium and calcium, two divalent metal ions prevalent in lithium-containing geothermal brines, were able to bind to ParaF, resulting in ¹⁹F NMR chemical shifts. The slow exchange between ParaF and magnesium enabled the simultaneous detection of lithium (which undergoes rapid exchange) and magnesium when both ions were present. This work provides a rational design principle for developing highly selective molecular lithium sensors.

{"title":"19F NMR-based lithium sensors using 19F-Labeled aza-crown ethers: Regioisomeric and substituent effects","authors":"Donghyeon Lee , Yanchuan Zhao , Byungjin Koo","doi":"10.1016/j.dyepig.2025.112762","DOIUrl":"10.1016/j.dyepig.2025.112762","url":null,"abstract":"<div><div>We herein report 19F NMR-based molecular lithium sensors using 19F-labeled aza-crown ether derivatives and investigate the regioisomeric and substituent effects on 19F NMR lithium sensing. Four new fluorinated 1-aza-12-crown-4 derivatives were successfully synthesized via Buchwald-Hartwig amination. Fluorine substitution at the para position relative to the 1-aza-12-crown-4 moiety resulted in a 20-fold increase in chemical shift differences upon exposure to lithium ions, compared to the meta position. We also found that an electron-withdrawing nitro group on the fluorobenzene aza-crown ether prevented any 19F NMR chemical shifts upon exposure to lithium ions. In contrast, a methyl substituent at the same position as the nitro group induced remarkable (∼20 fold) chemical shifts, similar to the compound without any functional group. In addition, magnesium and calcium, two divalent metal ions prevalent in lithium-containing geothermal brines, were able to bind to ParaF, resulting in 19F NMR chemical shifts. The slow exchange between ParaF and magnesium enabled the simultaneous detection of lithium (which undergoes rapid exchange) and magnesium when both ions were present. This work provides a rational design principle for developing highly selective molecular lithium sensors.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112762"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143627815","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Extending the conjugation of xanthene through N heteroatoms

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-13 DOI: 10.1016/j.dyepig.2025.112760

Daniel J. Frazier, Daniel M. Knauss

Polymers with small molecule chromophores incorporated into the conjugated backbone have shown excellent electronic properties for use in organic semiconductor applications. The incorporation of xanthene moieties, the central motif in fluorescein and rhodamine dyes, into a fully conjugated polymer backbone has yet to be fully investigated due to the inherent break in conjugation within the structure. This study reports the syntheses of four different low-molecular weight polymers via Buchwald-Hartwig polyamination composed of xanthene units linked through various amines. The N heteroatom linkage promotes conversion to the quinoidal form, which extends the conjugation through a hypothesized zwitterionic backbone. Evidence of extended conjugation is seen in the reduced optical band gaps of the polymers with the lowest band gap observed at 1.58 eV. Furthermore, air stable unpaired electrons were detected via electron paramagnetic resonance (EPR), suggesting a stabilized equilibrium between ionic and radical forms in the backbone. The design and characteristics inherent in the materials synthesized should provide intrinsic electrical conductivity and magnetic properties of interest.

{"title":"Extending the conjugation of xanthene through N heteroatoms","authors":"Daniel J. Frazier, Daniel M. Knauss","doi":"10.1016/j.dyepig.2025.112760","DOIUrl":"10.1016/j.dyepig.2025.112760","url":null,"abstract":"<div><div>Polymers with small molecule chromophores incorporated into the conjugated backbone have shown excellent electronic properties for use in organic semiconductor applications. The incorporation of xanthene moieties, the central motif in fluorescein and rhodamine dyes, into a fully conjugated polymer backbone has yet to be fully investigated due to the inherent break in conjugation within the structure. This study reports the syntheses of four different low-molecular weight polymers via Buchwald-Hartwig polyamination composed of xanthene units linked through various amines. The N heteroatom linkage promotes conversion to the quinoidal form, which extends the conjugation through a hypothesized zwitterionic backbone. Evidence of extended conjugation is seen in the reduced optical band gaps of the polymers with the lowest band gap observed at 1.58 eV. Furthermore, air stable unpaired electrons were detected via electron paramagnetic resonance (EPR), suggesting a stabilized equilibrium between ionic and radical forms in the backbone. The design and characteristics inherent in the materials synthesized should provide intrinsic electrical conductivity and magnetic properties of interest.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112760"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143641958","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Highly sensitive fluorescence probe for accurate detection of peroxynitrite in mitochondria and imaging inflammation sites 高灵敏度荧光探针，用于准确检测线粒体中的过氧化亚硝酸盐并为炎症部位成像

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-11 DOI: 10.1016/j.dyepig.2025.112756

Xiao-Lei Xue , Ru-Xing Chen , Jun-Yu Luan , Ying-Ying Shan , Kun-Peng Wang , Xiao-Zhong Xiang , Ying Fang , Shaojin Chen , Zhi-Qiang Hu

Peroxynitrite (ONOO⁻) plays a pivotal role in various physiological and pathological processes. The sensitive and specific detection of ONOO⁻ is of paramount significance for early diagnosis, treatment, and prognosis of diseases. In this study, a near-infrared (NIR) fluorescent probe was developed for the detection of ONOO⁻ with rapid responsiveness (less than 100 s). As the concentration of ONOO⁻ increases, the ratio of fluorescence intensities exhibited a robust linear relationship with ONOO⁻ concentration. Additionally, the probe demonstrated the ability to selectively detect changes in ONOO⁻ levels, with a limit of detection (LOD) value of 13 nM. Importantly, the probe was successfully employed to detect endogenous ONOO⁻ in living cells and mouse models. In conclusion, the fluorescent probe exhibits significant potential for elucidating disease processes induced by ONOO⁻.

过氧化亚硝酸盐（ONOO-）在各种生理和病理过程中发挥着关键作用。灵敏而特异地检测 ONOO- 对疾病的早期诊断、治疗和预后具有重要意义。本研究开发了一种近红外（NIR）荧光探针，用于快速（小于 100 秒）检测 ONOO-。随着 ONOO- 浓度的增加，荧光强度比与 ONOO- 浓度呈稳健的线性关系。此外，该探针还能选择性地检测 ONOO- 水平的变化，检测限（LOD）值为 13 nM。重要的是，该探针被成功用于检测活细胞和小鼠模型中的内源性 ONOO-。总之，该荧光探针在阐明ONOO-诱导的疾病过程方面具有巨大潜力。

{"title":"Highly sensitive fluorescence probe for accurate detection of peroxynitrite in mitochondria and imaging inflammation sites","authors":"Xiao-Lei Xue , Ru-Xing Chen , Jun-Yu Luan , Ying-Ying Shan , Kun-Peng Wang , Xiao-Zhong Xiang , Ying Fang , Shaojin Chen , Zhi-Qiang Hu","doi":"10.1016/j.dyepig.2025.112756","DOIUrl":"10.1016/j.dyepig.2025.112756","url":null,"abstract":"<div><div>Peroxynitrite (ONOO−) plays a pivotal role in various physiological and pathological processes. The sensitive and specific detection of ONOO− is of paramount significance for early diagnosis, treatment, and prognosis of diseases. In this study, a near-infrared (NIR) fluorescent probe was developed for the detection of ONOO− with rapid responsiveness (less than 100 s). As the concentration of ONOO− increases, the ratio of fluorescence intensities exhibited a robust linear relationship with ONOO− concentration. Additionally, the probe demonstrated the ability to selectively detect changes in ONOO− levels, with a limit of detection (LOD) value of 13 nM. Importantly, the probe was successfully employed to detect endogenous ONOO− in living cells and mouse models. In conclusion, the fluorescent probe exhibits significant potential for elucidating disease processes induced by ONOO−.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112756"},"PeriodicalIF":4.1,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143637618","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Insight into structure-property relationship of diazo-based carbene-type dyes towards high fixing performance on synthetic fiber

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-11 DOI: 10.1016/j.dyepig.2025.112755

Hua Jiang, Xiaokang Xie, Lulu Shi, Ye Wang

This paper investigated the reaction performance of diazo based carbene dyes with synthetic fibers, particularly the substituent effect of reactive group on fixation property of dyed fibers. Thus, a series of six azo dyes containing one diazo ester group were designed and synthesized. Their structures, absorption and thermal properties were firstly characterized. Four typical synthetic fibers, including polyurethane (PU), polyamide (PA), polyethylene terephthalate (PET), and polypropylene (PP) fibers, were dyed using the diazo type dyes in organic solvent followed by fixing the dyed fibers under high temperature. Substituent at α-position to diazo group was found to significantly affect the thermal stability of dye molecules and chemical reactivity of dyes with fibers. In donor-acceptor system, electron-withdrawing group on phenyl substituent increased the thermal stability of diazo moiety, and also largely improved the reactivity of dyes with various types of fibers. As comparison, diazo dyes having acceptor-acceptor system exhibited high thermal stability and needed more energy to initiate the reaction. However, these dyes, once initiated, presented higher reactivity with fibers, especially with PET fiber. The reaction mechanisms between dyes and synthetic fibers were reasonably speculated through small molecule simulation reactions and theoretical calculations, combined with the dye fixation results on fibers. All the aliphatic C–H or N–H bonds, as well as aromatic structures existed in fibers were possible sites for carbene reactions. These reactions included at least insertion reaction, addition reaction, and Wolff rearrangement reaction. N–H bond insertion reaction underwent much more easily than C–H bond insertion reaction, while addition reaction with phenyl group appeared the most difficult. Besides, carbonyl group lied in α-position to diazo group would induce a Wolff rearrangement reaction, which was also an efficient pathway for combining dyes with fibers containing N–H bonds.

{"title":"Insight into structure-property relationship of diazo-based carbene-type dyes towards high fixing performance on synthetic fiber","authors":"Hua Jiang, Xiaokang Xie, Lulu Shi, Ye Wang","doi":"10.1016/j.dyepig.2025.112755","DOIUrl":"10.1016/j.dyepig.2025.112755","url":null,"abstract":"<div><div>This paper investigated the reaction performance of diazo based carbene dyes with synthetic fibers, particularly the substituent effect of reactive group on fixation property of dyed fibers. Thus, a series of six azo dyes containing one diazo ester group were designed and synthesized. Their structures, absorption and thermal properties were firstly characterized. Four typical synthetic fibers, including polyurethane (PU), polyamide (PA), polyethylene terephthalate (PET), and polypropylene (PP) fibers, were dyed using the diazo type dyes in organic solvent followed by fixing the dyed fibers under high temperature. Substituent at α-position to diazo group was found to significantly affect the thermal stability of dye molecules and chemical reactivity of dyes with fibers. In donor-acceptor system, electron-withdrawing group on phenyl substituent increased the thermal stability of diazo moiety, and also largely improved the reactivity of dyes with various types of fibers. As comparison, diazo dyes having acceptor-acceptor system exhibited high thermal stability and needed more energy to initiate the reaction. However, these dyes, once initiated, presented higher reactivity with fibers, especially with PET fiber. The reaction mechanisms between dyes and synthetic fibers were reasonably speculated through small molecule simulation reactions and theoretical calculations, combined with the dye fixation results on fibers. All the aliphatic C–H or N–H bonds, as well as aromatic structures existed in fibers were possible sites for carbene reactions. These reactions included at least insertion reaction, addition reaction, and Wolff rearrangement reaction. N–H bond insertion reaction underwent much more easily than C–H bond insertion reaction, while addition reaction with phenyl group appeared the most difficult. Besides, carbonyl group lied in α-position to diazo group would induce a Wolff rearrangement reaction, which was also an efficient pathway for combining dyes with fibers containing N–H bonds.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112755"},"PeriodicalIF":4.1,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143620957","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis and reversible thermochromic behavior of diketopyrrolopyrrole dyes

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-10 DOI: 10.1016/j.dyepig.2025.112753

Hyungkyu Moon , T. Sheshashena Reddy , Myung-Seok Choi

The development of reversible thermochromic dyes without leuco dyes or bisphenol presents an ongoing challenge. In this study, reversible five thermochromic diketopyrrolopyrrole (DPP) dyes were synthesized and characterized (DPP1–5). The optical and thermal properties of the DPP dyes were investigated, and DPP dye microcapsules were also prepared and characterized. We first prepared and characterized microcapsules of DPP dyes and investigated their thermochromic properties. The effect of the phenyl or thiophene substituents attached to the DPP on the thermochromism of the dye was also investigated. Phenyl–based microcapsules DPP1–3 showed a slight color change from deep orange to light yellow upon gradual heating from 30 to 60 °C, whereas thiophene–based DPP dye microcapsules exhibited pronounced color changes from blue to red upon a gradual temperature increase from 30 to 60 °C.

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The critical role of the small singlet-triplet energy gap in heavy-atom containing TADF emitters for high performance electroluminescence

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2025-03-10 DOI: 10.1016/j.dyepig.2025.112752

Zhengqi Xiao , Yang Zou , Yanyun Jing , Ruihan Zhong , Xiaosong Cao , Jingsheng Miao , Chuluo Yang , Xiaojun Peng

Thermally activated delayed fluorescent (TADF) molecules are promising emitters for organic light-emitting diodes (OLEDs). However, they often experience significant efficiency roll-off at high brightness levels due to a relatively slow reverse intersystem crossing rate (k_RISC). Both a small singlet-triplet energy gap (ΔE_ST) and the heavy-atom effect have been shown to effectively accelerate the k_RISC of TADF emitters. Despite this, the interplay and relative importance of these two factors have rarely been explored. In this study, we designed two TADF emitters by connecting a selenium-containing electron donor with a triazine acceptor. Although both emitters share a similar molecular framework, the heavy-atom effect in the control emitter, which has a larger ΔE_ST, negatively impacts its optical properties, leading to a lower photoluminescence quantum yield (PLQY) and weaker TADF characteristics. In contrast, the emitter with a smaller ΔE_ST exhibits significantly better optical properties, including higher PLQY, much faster k_RISC, and consequently, improved device performance. This work highlights that a small ΔE_ST is the prerequisite for the heavy-atom effect to enhance k_RISC and optimize TADF molecule design.

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