Dyes and Pigments最新文献

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Carbon black doped amorphous photonic crystal pigments with highly saturated structural color
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-13 DOI: 10.1016/j.dyepig.2025.112646
Xiaoyu Bai, Qiang Zhao, Tongtong Cao, Yuhua Cao
{"title":"Carbon black doped amorphous photonic crystal pigments with highly saturated structural color","authors":"Xiaoyu Bai,&nbsp;Qiang Zhao,&nbsp;Tongtong Cao,&nbsp;Yuhua Cao","doi":"10.1016/j.dyepig.2025.112646","DOIUrl":"10.1016/j.dyepig.2025.112646","url":null,"abstract":"<div><div>The work reported a simple method for preparation of the powdery amorphous photonic crystal pigments with highly saturated colors. Monodispersed nanospheres P(St/MAA) were synthesized by soap-free emulsion polymerization using styrene (St) and methacrylic acid (MAA) as the monomers, and ammonium persulfate (APS) as the initiator to construct photonic crystals (PCs). P(St/MAA) PCs were doped with carbon black (CB) modified by cationic surfactant cetyltrimethylammonium bromide (CTAB) to enhance color saturation. When CTAB concentration increased to 4.75 mmol/L, the arrangement of the nanospheres P(St/MAA) doped CB modified with CTAB (CTAB-CB) transitioned from long-range to short-range ordering because of the strong electrostatic attraction between negatively charged P(St/MAA) and positively charged CTAB-CB, and the resulted PCs became amorphous photonic crystals (APCs). Whereas, the APCs exhibited highly saturated structural color due to the suppression of incoherently scattered light by CB. The short-range ordering of APCs could eliminate angle dependence. In addition, micron mica were added as pearlescent fillers to prepare CTAB-CB-mica-P(St/MAA), which improved the lightness and adhesion of the APCs as pigments. The P(St/MAA) nanospheres with tunable particle sizes were obtained by regulating the monomer concentration in soap-free emulsion polymerization. These P(St/MAA) nanospheres as building blocks constructed the APCs pigments with controllable structural colors such as blue, cyan, green, and red. CB modified with CTAB, mica and P(St/MAA) were mixed in aqueous solution by sonication, centrifugation, then dried and ground, the APCs powders were obtained and could be applied directly as pigments without PCs assembly further. These highly saturated APCs pigments have potential applications in the field of cosmetics.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112646"},"PeriodicalIF":4.1,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135036","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
Single-component thioxanthone-based photoinitiator for free-radical photopolymerization of acrylates via UV-LED irradiation
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-12 DOI: 10.1016/j.dyepig.2025.112640
Saihe Yang , Pengzhong Chen , Haichao Fu , Yu Li , Lu Li , Wenzheng Li , Shikun Song , Runfeng Xu , Qingze Pan , Yangyang Xin , Jiangli Fan , Xiaojun Peng
{"title":"Single-component thioxanthone-based photoinitiator for free-radical photopolymerization of acrylates via UV-LED irradiation","authors":"Saihe Yang ,&nbsp;Pengzhong Chen ,&nbsp;Haichao Fu ,&nbsp;Yu Li ,&nbsp;Lu Li ,&nbsp;Wenzheng Li ,&nbsp;Shikun Song ,&nbsp;Runfeng Xu ,&nbsp;Qingze Pan ,&nbsp;Yangyang Xin ,&nbsp;Jiangli Fan ,&nbsp;Xiaojun Peng","doi":"10.1016/j.dyepig.2025.112640","DOIUrl":"10.1016/j.dyepig.2025.112640","url":null,"abstract":"<div><div>In this study, three new efficient one-component type II photoinitiators (PIs) for free-radical polymerization of acrylate-type monomers under ultraviolet (UV) light-emitting diode (UV-LED) irradiation were synthesized by covalently linking different coinitiators with a thioxanthone chromophore using a methyl ester linker. UV–visible spectroscopy and electron spin resonance analysis confirmed the generation of free radicals through intramolecular reactions between hydrogen donor coinitiators and the thioxanthone moiety. Real-time Fourier-transform infrared spectroscopy was used to investigate the kinetics of photopolymerization of the prepared PIs. TX-A2 with benzodioxole as a coinitiator showed conversions of 90 % within 20 s for C<img>C double bonds and a polymerization rate of 10.9 %/s, performing considerably better than a commercial PI 2-isopropylthioxanthone and the prepared PIs with anisole and thioanisole coinitiators. These results highlight the significance of intramolecularly incorporated coinitiator moieties in enhancing the performance of efficient single-component type II PIs. In addition, TX-A2 was successfully used for curing color photoresist films, which could be patterned via photolithography and improved the stability of color pigments in the films toward light and heat, indicating its considerable potential in advanced manufacturing.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112640"},"PeriodicalIF":4.1,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135024","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
Study on the correlations between dynamic dye and structural colors
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-10 DOI: 10.1016/j.dyepig.2025.112643
Jie Zhou, Jinhui Liang, Yaru Meng, Xihe Wang, Kaixin Yang, Wenzhuo Ma, Shengjie Wang, Yongqing Xia
{"title":"Study on the correlations between dynamic dye and structural colors","authors":"Jie Zhou,&nbsp;Jinhui Liang,&nbsp;Yaru Meng,&nbsp;Xihe Wang,&nbsp;Kaixin Yang,&nbsp;Wenzhuo Ma,&nbsp;Shengjie Wang,&nbsp;Yongqing Xia","doi":"10.1016/j.dyepig.2025.112643","DOIUrl":"10.1016/j.dyepig.2025.112643","url":null,"abstract":"<div><div>In nature, many creatures, such as lizards and octopuses, have the remarkable ability to exhibit color changes by precisely locating different types of chromatophores, which contain both pigment cells and iridophores. Though the evolution of structural coloration and pigments in some animals has been explored, there is a critical gap between the natural skin color and the biomimicry color. In this work, we designed smart artificial skins that can produce extensive color by incorporating physical color and chemical colors together, similar to the integumentary structure of lizards. The mechanochromic hydrogel films embedded with colloidal crystals provide a dynamic structural color background, and the dyes entrapped in the hydrogels tune the composite color precisely. The composite color was computed by Grassmann's law and further quantitatively analyzed by the RGB and HSB color spaces. The computed results agree reasonably well with the experimental results. Thus, precise colors that are difficult to produce by only structural colors or dyes can be achieved by theoretical calculation. Furthermore, films with more realistic color are achieved by incorporating pH-responsive dye with tunable structural color, similar to the color-changing mechanism of lizards. This work may open a new strategy for preparing color-displaying devices with outstanding performance.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112643"},"PeriodicalIF":4.1,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135540","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
Novel axial fullerenol-substituted hyperbranched phthalocyanines:Synthesis, photophysical and nonlinear optical properties
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-10 DOI: 10.1016/j.dyepig.2025.112642
Haonan Xu , Yuping Han , Danying Zhao , Zheng Liu , Guibin Wang , Yunhe Zhang
{"title":"Novel axial fullerenol-substituted hyperbranched phthalocyanines:Synthesis, photophysical and nonlinear optical properties","authors":"Haonan Xu ,&nbsp;Yuping Han ,&nbsp;Danying Zhao ,&nbsp;Zheng Liu ,&nbsp;Guibin Wang ,&nbsp;Yunhe Zhang","doi":"10.1016/j.dyepig.2025.112642","DOIUrl":"10.1016/j.dyepig.2025.112642","url":null,"abstract":"<div><div>In this study, we designed and synthesized a novel hyperbranched structure of phthalocyanine compound, which was axially linked with fullerenol to form a D-A (donor and acceptor) type compound HLaPc-C<sub>60</sub>(OH)<sub>n</sub>. In this configuration, phthalocyanine acts as the electron donor, while fullerenol as the acceptor. The formation of hyperbranched structures and the introduction of fullerenol expanded the π-conjugation system and weakened the aggregation phenomenon. The unique three-dimensional hyperbranched structure with abundance of D-A enhances the photoinduced intramolecular electron transfer (PET) and energy transfer (ET) processes. This improvement contributes to the compound's excellent nonlinear optical properties. In addition, we prepared a PPSU-based composite film (HLaPc-C<sub>60</sub>(OH)<sub>n</sub>/PPSU) in which the interaction between the similar sulfonyl structures and HLaPc enhances its dispersion. The values of large third-order nonlinear susceptibility (Im[χ<sup>(3)</sup>]) of 2.20 × 10<sup>−8</sup> esu and a low limit threshold (Ilim) of 0.91 J/cm<sup>2</sup> demonstrate that the composite film material has considerable potential applications as optical limiters.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112642"},"PeriodicalIF":4.1,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135030","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
High mobility wide bandgap polymer donors based on benzobisoxazole for polymer solar cells
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-10 DOI: 10.1016/j.dyepig.2025.112645
Hui Sheng , Jianan Niu , Shizhao Liu , Shuguang Wen , Mingliang Sun , Xichang Bao
{"title":"High mobility wide bandgap polymer donors based on benzobisoxazole for polymer solar cells","authors":"Hui Sheng ,&nbsp;Jianan Niu ,&nbsp;Shizhao Liu ,&nbsp;Shuguang Wen ,&nbsp;Mingliang Sun ,&nbsp;Xichang Bao","doi":"10.1016/j.dyepig.2025.112645","DOIUrl":"10.1016/j.dyepig.2025.112645","url":null,"abstract":"<div><div>The performance of polymer solar cells (PSCs) has rapidly developed, benefitting from the advancements in crescent-shaped small molecule acceptors (SMAs). The polymer donors that match with SMAs are mostly aimed at generating more excitons, and therefore their optical bandgaps (<span><math><mrow><msubsup><mi>E</mi><mi>g</mi><mtext>opt</mtext></msubsup></mrow></math></span>) are typically moderate. However, from the perspective of efficient and sufficient energy utilization, the development of wide bandgap polymer donors with maximum absorption peaks closer to 500 nm is still of great significance, as it allows for the utilization of the strongest region of solar radiation energy. Here, we designed and synthesized two polymer donors based on benzobisoxazole with different molecular backbones, namely PBBO-1 and PBBO-2. They have wide <span><math><mrow><msubsup><mi>E</mi><mi>g</mi><mtext>opt</mtext></msubsup></mrow></math></span> of 2.01 eV and 2.15 eV, respectively. Additionally, without halogen groups, they exhibit deep HOMO energy levels of −5.43 eV and −5.56 eV, respectively. Due to their good planarity, both exhibit a high hole mobility of ∼7 × 10<sup>−4</sup> cm<sup>2</sup> V⁻<sup>1</sup> s⁻<sup>1</sup> after blending with Y6. As a result, PBBO-1:Y6, which has a more ideal morphology and overall better photovoltaic conversion dynamics, achieved a PCE of 9.90 %, surpassing the PCE of 8.99 % for PBBO-2:Y6. This work provides a new strategy for designing high mobility wide bandgap polymer donors.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112645"},"PeriodicalIF":4.1,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135026","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
Elastic organic crystals for flexible lasing media synthesized by crystal engineering
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-09 DOI: 10.1016/j.dyepig.2025.112639
Rui Huang , Yijiao Wang , Yuting Huang , Mengke Wang , Shuangquan Liao
{"title":"Elastic organic crystals for flexible lasing media synthesized by crystal engineering","authors":"Rui Huang ,&nbsp;Yijiao Wang ,&nbsp;Yuting Huang ,&nbsp;Mengke Wang ,&nbsp;Shuangquan Liao","doi":"10.1016/j.dyepig.2025.112639","DOIUrl":"10.1016/j.dyepig.2025.112639","url":null,"abstract":"<div><div>Flexible organic crystals have attracted a lot of attention due to their potential applications in flexible sensors and devices. The deformation mechanism of organic crystals is still controversial, which limits their development. Herein, we synthesized two types of elastic crystals (<strong>1</strong> and <strong>2 GC)</strong> using molecular structure regulation. In addition, we obtained the brittle crystal <strong>2 YC</strong> by optimizing the supramolecular structures of <strong>2 GC</strong>. The crystal structure data of all these polymorphs explain why different molecules and polymorphs exhibit different mechanical properties. Furthermore, in the application of optical waveguides and amplified spontaneous emission, they both demonstrate excellent performance, fully reflecting their elasticity and providing ideal conditions for studying the principle of flexibility.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112639"},"PeriodicalIF":4.1,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135027","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
Sizing-up the aromatic system of a cyclometalated N-heterocyclic carbene in a luminescent platinum-based sensor to xanthine
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-09 DOI: 10.1016/j.dyepig.2025.112641
Irene Melendo , Javier Camacho-Aguayo , Sara Fuertes , Antonio Martín , Susana de Marcos , Javier Galbán , Violeta Sicilia
{"title":"Sizing-up the aromatic system of a cyclometalated N-heterocyclic carbene in a luminescent platinum-based sensor to xanthine","authors":"Irene Melendo ,&nbsp;Javier Camacho-Aguayo ,&nbsp;Sara Fuertes ,&nbsp;Antonio Martín ,&nbsp;Susana de Marcos ,&nbsp;Javier Galbán ,&nbsp;Violeta Sicilia","doi":"10.1016/j.dyepig.2025.112641","DOIUrl":"10.1016/j.dyepig.2025.112641","url":null,"abstract":"<div><div>A cyclometalated N-heterocyclic carbene platinum(II) complex comprising a phenanthrenyl moiety has been prepared and used to synthesize neutral and cationic luminescent complexes containing different ancillary ligands: [Pt(Phen^C∗)(acac)] (<strong>5</strong>), [Pt(Phen^C∗)(CNXyl)<sub>2</sub>]PF<sub>6</sub> (<strong>6</strong>) and [Pt(Phen^C∗)(P^P)]PF<sub>6</sub> (P^P: 1,1-bis(diphenylphosphino)methane, dppm <strong>7</strong>; 1,2-bis(diphenylphosphino)ethane, dppe, <strong>8</strong>, 1,2-bis(diphenylphosphino)benzene, dppbz, <strong>9</strong>). Structural characterization by NMR and single-crystal X-ray studies endorsed the proposed molecular structure for these complexes with the formation of a six-membered platinacycle. Photophysical and computational studies for <strong>5–9</strong> disclosed the ligand-centered nature of the triplet state, mainly governed by the extended aromatic system of the Phen^C∗ ligand. Immobilized in ethyl cellulose (EC) films, compound <strong>5</strong> shows elevated quantum yield and long decay times in argon atmosphere and high sensitivity to molecular oxygen. Blends of <strong>5</strong> and EC (<strong>C5</strong>) were tested as a luminescent oxygen probe for the determination of xanthine (Xn), showing good photo stability and reversibility. The RSD is 0.9 % (n = 3) for 3·10<sup>−4</sup> M and the detection limit achieves values of ∼2·10<sup>−5</sup> M. This platinum-based sensor delivers better results than the ones obtained with [Ru(bpy)<sub>3</sub>]Cl<sub>2</sub>·6H<sub>2</sub>O, a typical luminophore used in commercial oxygen sensors. To improve the feasibility of the Xn determination, the sensor was implemented in a smartphone adapted device to be used as a in-situ Xn control.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112641"},"PeriodicalIF":4.1,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135029","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
Cyanine dyes from novel dihydrophenanthrene derivatives
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-08 DOI: 10.1016/j.dyepig.2025.112635
Arunkumar Easwaran
{"title":"Cyanine dyes from novel dihydrophenanthrene derivatives","authors":"Arunkumar Easwaran","doi":"10.1016/j.dyepig.2025.112635","DOIUrl":"10.1016/j.dyepig.2025.112635","url":null,"abstract":"<div><div>Dihydrophenanthrene derived novel indolenines synthesized and characterized. Both the isomeric indolenines were isolated using automated flash chromatography. The newly synthesized isomers were converted to the indolium salt followed by symmetric and unsymmetric cyanine dye synthesis. The dihydrophenanthrene (DHP) based symmetric cyanines in comparison to the asymmetric DHP- indolium cyanines showed an additional red shift in the absorption and emission properties of the dyes due to the extra conjugation coming from the DHP ring. Unsubstituted DHP based symmetric cyanines showed strong aggregation under aqueous conditions. All dyes showed a negative solvatochromic behavior in both absorption and emission studies.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112635"},"PeriodicalIF":4.1,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135031","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
Advancements in NIR-based fluorescence imaging agents for oral oncology: A comprehensive review
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-08 DOI: 10.1016/j.dyepig.2025.112637
Amal Adnan Ashour , Alaa Shafie , Ali Alqarni , Mohammed Fareed Felemban
{"title":"Advancements in NIR-based fluorescence imaging agents for oral oncology: A comprehensive review","authors":"Amal Adnan Ashour ,&nbsp;Alaa Shafie ,&nbsp;Ali Alqarni ,&nbsp;Mohammed Fareed Felemban","doi":"10.1016/j.dyepig.2025.112637","DOIUrl":"10.1016/j.dyepig.2025.112637","url":null,"abstract":"<div><div>NIR-based fluorescence imaging agents have emerged as a powerful diagnostic tool for early detection and monitoring of different types of cancer, offering high sensitivity, real-time visualization, and non-invasive assessment. This review explores recent advancements in NIR-based fluorescence imaging agents for oral oncology, focusing on the development and application of diverse imaging probes. Organic dyes, with their high fluorescence quantum yields and tunable spectral properties, have been extensively investigated for targeted imaging of cancer biomarkers. Additionally, nanomaterials such as quantum dots, gold nanoparticles, and carbon-based systems have demonstrated significant potential due to their unique optical properties, enhanced photostability, and ability to deliver multifunctional imaging and therapeutic capabilities. The integration of these innovative imaging agents with advanced fluorescence techniques has significantly improved the accuracy of oral cancer diagnosis and treatment monitoring.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112637"},"PeriodicalIF":4.1,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135032","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
Immobilization of the hydrazone configuration via decyanidation for pyridone based heterocyclic dyes showing enhanced pH stability
IF 4.1 3区 工程技术
Dyes and Pigments Pub Date : 2025-01-06 DOI: 10.1016/j.dyepig.2025.112634
Xiao-Lei Zhao , Hao-Ran Li , Bo Yang , Wei Huang
{"title":"Immobilization of the hydrazone configuration via decyanidation for pyridone based heterocyclic dyes showing enhanced pH stability","authors":"Xiao-Lei Zhao ,&nbsp;Hao-Ran Li ,&nbsp;Bo Yang ,&nbsp;Wei Huang","doi":"10.1016/j.dyepig.2025.112634","DOIUrl":"10.1016/j.dyepig.2025.112634","url":null,"abstract":"<div><div>Disperse dyes having pyridine-2,6-dione based coupling components often suffer from deteriorated uniformity in the fiber-dyeing processes due to pH-induced azo-hydrazone tautomerism. To overcome this deficiency, the functional group transformation (FGT) strategy was employed to convert the cyano group of one pyridine-2,6-dione derivative to a less electron-withdrawing amide group or even a hydrogen atom, so as to hinder the transformation from the hydrazone form to deprotonated azo form, and hence improve the acid-base stability of the target dyes. As a result, six new hydrazone dyes were synthesized with strong acid-base stability, which can be confirmed by related UV–Vis spectra. Reduced charge delocalization in the modified dyes, weakened molecular polarization, and increased energy barrier for the intramolecular transfer of the hydrazone proton were believed to play important roles in the fixation of hydrazone configuration for the new dyes. Detailed theoretical calculations further demonstrated the increased conversion energy barriers. The X-ray crystal structure analysis revealed that the decyano pyridine-2,6-dione dyes contain denser fused six-membered intramolecular hydrogen-bonding rings, and the hydrogen bond lengths are significantly shorter than those in previously reported pyridine-2,6-dione based dyes, which further stabilize the hydrazone protons of dyes in this work. The fundamental FGT strategy elucidated in this study is suggested to be helpful in the improvement of dyeing performance for a wide variety of existing hydrazone dyes.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112634"},"PeriodicalIF":4.1,"publicationDate":"2025-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135539","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
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