Dyes and PigmentsPub Date : 2025-01-21DOI: 10.1016/j.dyepig.2025.112655
Ziting Ma , Fuyang Gu , Xiaoyan Wang , Guowei Xiao , Yang Jiang , Jinmei Du , Liang He , Yongjun Yu , Xiyu Song , Changhai Xu
{"title":"Preparation of stable liquid disperse dye using the antisolvent precipitation method for enhancing dyeability and eco-friendliness","authors":"Ziting Ma , Fuyang Gu , Xiaoyan Wang , Guowei Xiao , Yang Jiang , Jinmei Du , Liang He , Yongjun Yu , Xiyu Song , Changhai Xu","doi":"10.1016/j.dyepig.2025.112655","DOIUrl":"10.1016/j.dyepig.2025.112655","url":null,"abstract":"<div><div>The objective of this study is to identify the optimal conditions for preparing liquid disperse dyes via the antisolvent precipitation method. Conventional liquid disperse dyes are typically produced via a top-down process, which possesses inherent limitations including high energy consumption. Antisolvent precipitation, as a bottom-up method, has not yet been widely adopted in commercial production of liquid disperse dye products. Utilizing this method to prepare dye suspensions could potentially reduce the energy consumption associated with the production of liquid disperse dyes. Herein, the particle size of dyes precipitated in the antisolvent was controlled by introducing surfactants at the early stage of precipitation, successfully producing small particle size liquid dispersions. The dye particle size was 10 μm before adding the dp510 dispersant and decreased to 242 nm afterward. The effect of different process parameters on the particle size, stability and dyeing properties were investigated.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112655"},"PeriodicalIF":4.1,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167912","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}
Dyes and PigmentsPub Date : 2025-01-21DOI: 10.1016/j.dyepig.2025.112667
Yuanyuan Zhou , Yaohua Shi , Shuaishuai Shen , Miao Li , Xiaodan Tang , Ruiping Qin , Zheng Tang , Jinsheng Song
{"title":"Simple nonfullerene acceptors achieving NIR absorption regulation via alkoxy functionalization on the π-spacers","authors":"Yuanyuan Zhou , Yaohua Shi , Shuaishuai Shen , Miao Li , Xiaodan Tang , Ruiping Qin , Zheng Tang , Jinsheng Song","doi":"10.1016/j.dyepig.2025.112667","DOIUrl":"10.1016/j.dyepig.2025.112667","url":null,"abstract":"<div><div>Non-fused ring acceptors (NFRAs) with simple molecular structure shows a bright prospect for high efficiency acceptors in commercial applications due to the easy synthesis and low cost. Herein, ethylhexyloxy is selected as the side chain on the π-spacer of the A-π-D-π-A type NFRAs, the orientation direction and amount have been carefully considered, which could regulate the band-edges of the absorption spectra ranging from 900 nm to 1120 nm. Hence, the inner alkoxy modified <strong>DTC-O</strong><sub><strong><em>i</em></strong></sub><strong>T-4F</strong> could reach a rather narrow bandgap of 1.10 eV due to the conformation locks, while the outer derived strategy in <strong>DTC-O</strong><sub><strong><em>o</em></strong></sub><strong>T-4F</strong> and <strong>DTC-O</strong><sub><strong><em>oi</em></strong></sub><strong>T-4F</strong> is effective at the LUMO improving. Utilization of PBDB-T as the donor, organic solar cells are constructed with these acceptors, and power conversion efficiencies (PCEs) of 5.50 %, 10.02 % and 10.58 % are acquired for <strong>DTC-O</strong><sub><strong><em>i</em></strong></sub><strong>T-4F</strong>, <strong>DTC-O</strong><sub><strong><em>o</em></strong></sub><strong>T-4F</strong> and <strong>DTC-O</strong><sub><strong><em>oi</em></strong></sub><strong>T-4F</strong> based devices, respectively. The conformation prediction, morphology study, crystallization orientation and energy loss analysis have been fully discussed in this work. In all, our studies have demonstrated that appropriate utilization of the alkoxy side chain on the π-spacer of the noncovalently locked simple A-π-D-π-A acceptors could effectively change its electronic characteristics and may offer some simple strategy for the design of high efficiency NFRAs.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112667"},"PeriodicalIF":4.1,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167868","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}
Dyes and PigmentsPub Date : 2025-01-20DOI: 10.1016/j.dyepig.2025.112664
Thanh Chung Pham , Hyejin Kim , Van Kieu Thuy Nguyen , Yeonghwan Choi , Hyun Wook Kang , Songyi Lee
{"title":"Donor-imine-acceptor-based small organic molecule for efficient photothermal therapy","authors":"Thanh Chung Pham , Hyejin Kim , Van Kieu Thuy Nguyen , Yeonghwan Choi , Hyun Wook Kang , Songyi Lee","doi":"10.1016/j.dyepig.2025.112664","DOIUrl":"10.1016/j.dyepig.2025.112664","url":null,"abstract":"<div><div>The development of small molecules with high photothermal conversion efficiency (PCE) poses a significant challenge in the context of photothermal therapy, a promising modality for cancer treatment. While certain efficient small molecules have been documented in the literature, they often incorporate bulky alkyl chains and/or aromatic rings to enhance the photothermal effect. Hence, this study presents a novel and straightforward method for synthesizing a photothermal small molecule, designated as <strong>PA2</strong>, utilizing a donor-acceptor framework. In this framework, diphenylamine is employed as the donor moiety, while 1,3-Bis(dicyanomethylidene)indan is utilized as the acceptor moiety. <strong>PA2</strong> demonstrated high PCE in both monomer and but also in aggregate state. In which, the excitation energy is efficiently released as heat via non-radiative decay through the conical intersection (CI) as confirmed by a computationally optimized minimum energy crossing point (MECP) and a combination of further theoretical studies and experimental control groups (<strong>PA3</strong> and <strong>PA4</strong>). Notably, the resulting molecular architecture exhibits remarkable efficacy in inhibiting tumor growth after a 10-day photothermal therapy period. Furthermore, <em>in vivo</em> experiments in a mouse tumor model demonstrate the favorable biocompatibility of these photothermal small molecules, signifying their suitability for safe application in biomedical contexts. This study makes a substantial contribution to the field of photothermal therapy by introducing a novel molecular design paradigm based on small molecules.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112664"},"PeriodicalIF":4.1,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167862","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}
Dyes and PigmentsPub Date : 2025-01-20DOI: 10.1016/j.dyepig.2025.112666
Mewenn Yvin , Elise Michel , Rémi Métivier , Laurent Galmiche , Lucas Frédéric , Clémence Allain , Pierre Audebert
{"title":"Fluorogenic heptazines functionalized with tetrazine rings for conjugation through inverse Electron Demand Diels-Alder reaction","authors":"Mewenn Yvin , Elise Michel , Rémi Métivier , Laurent Galmiche , Lucas Frédéric , Clémence Allain , Pierre Audebert","doi":"10.1016/j.dyepig.2025.112666","DOIUrl":"10.1016/j.dyepig.2025.112666","url":null,"abstract":"<div><div>Fluorogenic probes that can selectively target molecules or materials thanks to click chemistry are promising tools for labelling or functionalization. Heptazines are heterocycles that gather appealing electrochemical and photophysical properties, combining high photooxidation potentials with long fluorescence lifetimes. However, selective grafting of molecular heptazines on a substrate is still underdeveloped. In this work, we report the synthesis, photophysical and electrochemical properties of two heptazine derivatives conjugated with one and three tetrazine rings respectively. These heptazines conjugated to tetrazines are very weakly fluorescent. We demonstrate that they can react in a fast manner with a strained alkyne, through an Inverse Electron Demand Diels-Alder reaction. This reaction has been followed thanks to a home-built photokinetics setup: in a timecale of a few seconds blue emitting heptazine pyridazine conjugates are generated with an 8.6 to 13.6 fluorescence turn-on.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112666"},"PeriodicalIF":4.1,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167914","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dyes and PigmentsPub Date : 2025-01-20DOI: 10.1016/j.dyepig.2025.112661
Ying Sun, Ying An, Jiajun Huang, Zhenming Yin
{"title":"Bis-arylazo-naphthobipyrrole: Synthesis, structure, photophysical properties, DFT calculations and anions sensing","authors":"Ying Sun, Ying An, Jiajun Huang, Zhenming Yin","doi":"10.1016/j.dyepig.2025.112661","DOIUrl":"10.1016/j.dyepig.2025.112661","url":null,"abstract":"<div><div>Three bis-arylazo-naphthobipyrrole compounds (<strong>1</strong>–<strong>3</strong>) with different substituents (-H, -Cl, and –OCH<sub>3</sub>) have been synthesized. The planar structure of compound <strong>1</strong> was characterized by X-ray crystallography. All compounds exhibit <em>λ</em><sub>max</sub> absorption at the range of 534–549 nm, and weakly fluorescence at the range of 599–628 nm due to the extended π-conjugation. All the compounds also show solvatochromic properties to chlorinated solvents. DFT calculations indicated that the compounds prefer to adopt planar <em>E</em>-<em>syn</em>/<em>E</em>-<em>syn</em> configuration. The frontier molecular orbitals (FMOs), energy gaps (ΔE) and UV–Vis spectra of these compounds were also evaluated by DFT calculations. UV–Vis titration experiments revealed that all the compounds can selectively sensing fluoride ion in DMSO solution.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112661"},"PeriodicalIF":4.1,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167864","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}
{"title":"Synthesis and photophysical properties of 6-aryl-2,4-bis(2′-hydroxyphenyl)pyrimidines ligands and their boron fluoride complexes","authors":"Clément Diguet , Amparo Navarro , M. Paz Fernández-Liencres , Sonia B. Jiménez-Pulido , Nuria A. Illán-Cabeza , Julien Massue , Sébastien Gauthier , Françoise Robin-le Guen , Sylvain Achelle , Julián Rodríguez-López","doi":"10.1016/j.dyepig.2025.112660","DOIUrl":"10.1016/j.dyepig.2025.112660","url":null,"abstract":"<div><div>A new family of 6-aryl-2,4-bis(2′-hydroxyphenyl)pyrimidines has been efficiently synthesized and characterized using Suzuki-Miyaura reactions, demonstrating their ability to function as rigid tridentate O^N^O chelating ligands for the preparation of four-coordinate organoboron compounds. Similar to related structures, the uncoordinated compounds do not exhibit fluorescence in either solution or the solid state. The intramolecular hydrogen bonds in their molecular structure promote an excited-state intramolecular proton transfer (ESIPT) process, leading to an excited keto tautomer that deactivates through non-radiative decay. Protonation and boron complexation can successfully inhibit the ESIPT process, resulting in fluorescence recovery, which can be finely tuned by modifying the substituents on the aryl group. Advanced techniques, including X-ray diffraction, density functional theory (DFT), and time-dependent DFT (TD-DFT), provide critical insights into the electronic structure and emission properties. This work offers a deeper understanding of the role of boron chelation in modulating emission properties, opening new avenues for the design of functional fluorescent materials.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112660"},"PeriodicalIF":4.1,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167865","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dyes and PigmentsPub Date : 2025-01-19DOI: 10.1016/j.dyepig.2025.112663
Xiuqian Ding , Yong Wang , Jingxi Nan , Xue Wu , Xin Zhou
{"title":"Synthesis of phosphate-substituted near-infrared dyes for photoacoustic imaging and photothermal therapy","authors":"Xiuqian Ding , Yong Wang , Jingxi Nan , Xue Wu , Xin Zhou","doi":"10.1016/j.dyepig.2025.112663","DOIUrl":"10.1016/j.dyepig.2025.112663","url":null,"abstract":"<div><div>Photothermal therapy (PTT) can effectively ablate hypoxic tumors in deep issue under the near-infrared (NIR) irradiation. The development of novel NIR photothermal agents with high molar absorption coefficient and photothermal conversion efficiency is highly demanded. In this work, two phosphate-substituted xanthene dyes (<strong>POM</strong> and <strong>P7</strong>) were synthesized, and their stability and photothermal conversion efficiency were investigated. Both of them showed board absorption around 700 nm in the aqueous solution. In comparison with the rigid <strong>POM</strong>, <strong>P7</strong> with flexible and twisted core displayed a higher photothermal conversion efficiency. The nanoparticle encapsulated in amphiphilic polymers (<strong>P7 NPs</strong>) was further used in the photoacoustic imaging-guided photothermal therapy <em>in vivo</em>.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112663"},"PeriodicalIF":4.1,"publicationDate":"2025-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167863","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}
Dyes and PigmentsPub Date : 2025-01-19DOI: 10.1016/j.dyepig.2025.112662
Teófanes B. Serna, Dora G. Felipe, Acácio A. Andrade, Viviane Pilla
{"title":"Thermo-optical characterization of fluorescent materials based on edible vegetable oils","authors":"Teófanes B. Serna, Dora G. Felipe, Acácio A. Andrade, Viviane Pilla","doi":"10.1016/j.dyepig.2025.112662","DOIUrl":"10.1016/j.dyepig.2025.112662","url":null,"abstract":"<div><div>This work evaluated the thermo-optical characterization of several vegetable oils such as <em>Persea gratissima</em> (avocado oil, AO), <em>Mauritia flexuosa Linnaeus filius</em> (buriti oil, BO), <em>Passiflora edulis</em> (passion fruit oil, PFO), and <em>Plukenetia volubilis</em> L. (Sacha inchi oil, SIO)<em>.</em> Vegetable oils are nontoxic, nonvolatile, nondepletable, and biodegradable resources used for several applications, such as in the foods, cosmetic, lubricant, coating, and pharmaceutical industries, due to their possible antioxidant and antimicrobial activities. In this work, the refractive index temperature coefficients (<em>dn/dT</em>) of AO, BO, PFO, and SIO were characterized as a function of temperature (296-329 K<sup>−1</sup>) via a Mach–Zehnder interferometer. The thermal diffusivity (<em>D</em>) and fluorescence quantum efficiency (<em>η</em>) were determined via the dual-beam mode-mismatched thermal lens (TL) technique. Fluorescence and time-resolved fluorescence measurements corroborate the TL results. AO presented a relatively higher <em>η</em> value than other vegetable oils did (BO, PFO, and SIO), and avocado oil was heat treated at 180 °C for the synthesis of carbon dots (C<sub>AO</sub>-dots). The <em>η</em> and fluorescence lifetime (<em>τ</em>) results obtained for the avocado-based nanoparticles were compared with those of other C-dots using oil as a carbon source, aiming at potential bioapplications.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"236 ","pages":"Article 112662"},"PeriodicalIF":4.1,"publicationDate":"2025-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167915","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}
Dyes and PigmentsPub Date : 2025-01-19DOI: 10.1016/j.dyepig.2025.112654
Yongqi Wang , Ting Lan , Nan Ji , Qinghua Meng , Wei He
{"title":"Advancements in Spiropyran probes: Mechanisms, applications in detection and imaging","authors":"Yongqi Wang , Ting Lan , Nan Ji , Qinghua Meng , Wei He","doi":"10.1016/j.dyepig.2025.112654","DOIUrl":"10.1016/j.dyepig.2025.112654","url":null,"abstract":"<div><div>Spiropyrans are classic molecular switching compounds that can reversibly transition between the closed-loop structure (spiropyran, SP) and the open-loop structure (merocyanine, MC) in response to external stimuli. These isomers exhibit distinct spectral characteristics and noticeable color changes due to their differing structural properties. This unique behavior makes spiropyrans highly applicable for the detection and imaging of various analytical targets. Furthermore, the reversible nature of these isomers enhances their utility. This article presents a comprehensive review of the applications of small-molecule spiropyran derivatives in chemical sensing and biological imaging from 2015 to 2024. It covers Photochromism detection applications for metal ions (Al<sup>3+</sup>, Li<sup>+</sup>, Ca<sup>2+</sup>, Cu<sup>2+</sup>, Pb<sup>2+</sup>, Cr<sup>3+</sup>, Ce<sup>3+</sup>, Fe<sup>2+</sup>), anions (CN<sup>⁻</sup>), small molecules (SO<sub>2</sub>, H<sub>2</sub>S, N<sub>2</sub>H<sub>4</sub>), and nucleic acids (calf thymus DNA). Additionally, Acidochromism has been utilized for pH detection in live cells, P. aeruginosa, and zebrafish, and for monitoring lysosomal pH changes. Solvatochromism enables the detection of metal ions (Cu<sup>2+</sup>), anions (CN<sup>⁻</sup>), and polarity changes in lysosomes. Furthermore, Thermochromism is employed for metal ion detection (Cu<sup>2+</sup>) and monitoring vaccine misuse.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"238 ","pages":"Article 112654"},"PeriodicalIF":4.1,"publicationDate":"2025-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143521022","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}
Dyes and PigmentsPub Date : 2025-01-17DOI: 10.1016/j.dyepig.2025.112656
Yutian Jiao, Yu Liu, Gongli Wei, Ce Wang, Baocai Xu, Li Zhao
{"title":"A novel tetraphenylbenzene-derived fluorescent probe for the detection of protamine and heparin","authors":"Yutian Jiao, Yu Liu, Gongli Wei, Ce Wang, Baocai Xu, Li Zhao","doi":"10.1016/j.dyepig.2025.112656","DOIUrl":"10.1016/j.dyepig.2025.112656","url":null,"abstract":"<div><div>In this study, we present an amphiphilic aggregation-induced emission fluorescent probe based on tetraphenylbenzene. The probe exhibited sensitive and selective detection of protamine through a “turn-on” fluorescence signal driven by electrostatic binding. A linear correlation was established between fluorescence intensity and protamine concentration in the range of 0.8–3 μg/mL in 4-(2-hydroxyethyl)piperazine-1-ethane-sulfonic acid (HEPES) buffer, with a limit of detection (LOD) of 6.65 ng/mL. Protamine detection was successfully demonstrated in a 0.3 % serum sample. Additionally, the electrostatic probe–protamine complex was able to detect heparin owing to the strong affinity between protamine and heparin, which was confirmed through a “turn-off” fluorescence response. The probe's sensitivity and selectivity for heparin detection were validated, with an LOD of 8.83 ng/mL and a linear working range of 1.0–2.2 μg/mL in HEPES buffer.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"235 ","pages":"Article 112656"},"PeriodicalIF":4.1,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143135025","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}