Dyes and PigmentsPub Date : 2025-08-27DOI: 10.1016/j.dyepig.2025.113142
Wen-Yu Lu , Ming-Yang Zhang , Xin-Yue Li , Xi-Xi Wu , Hui-Sheng Ge , Hui-Jing Li , Yan-Chao Wu
{"title":"Imaging of cysteine in cells and tumor mice using water-soluble near-infrared fluorescence probe with a large Stokes shift","authors":"Wen-Yu Lu , Ming-Yang Zhang , Xin-Yue Li , Xi-Xi Wu , Hui-Sheng Ge , Hui-Jing Li , Yan-Chao Wu","doi":"10.1016/j.dyepig.2025.113142","DOIUrl":"10.1016/j.dyepig.2025.113142","url":null,"abstract":"<div><div>As a vital biological thiol, cysteine (Cys) is closely linked to cancer progression and plays a pivotal role in protecting the body against oxidative stress. Therefore, the development of near-infrared (NIR) fluorescent probes with high sensitivity and selectivity for in vivo detection of Cys is significant. In this study, a water-soluble, NIR \"turn-on\" fluorescent probe (<strong>CQAI</strong>) is developed by integrating coumarin derivatives with acrylate moieties. The introduction of <em>N</em>-methylquinolinium into the fluorophore scaffold endows the probe with significantly enhanced water solubility and a remarkable Stokes shift of 255 nm. The fluorescence of <strong>CQAI</strong> is initially quenched due to the suppression of the intramolecular charge transfer (ICT) process and the activation of the photoinduced electron transfer (PET) mechanism. Upon interaction with Cys, a distinct fluorescence emission at 755 nm is observed. The dual-quenching mechanism of <strong>CQAI</strong> offers a high imaging contrast, exceptional selectivity (unaffected by potential interferents such as homocysteine, glutathione, and hydrogen sulfide), and excellent sensitivity, with a detection limit as low as 0.14 μM. Owing to its high cellular permeability and low cytotoxicity, <strong>CQAI</strong> effectively detects both endogenous and exogenous Cys in living cells. Furthermore, it enables the monitoring of Cys levels in tumor-bearing mice, taking advantage of its long-wavelength fluorescence for deep-tissue imaging. The superior performance of <strong>CQAI</strong> highlights its outstanding potential as a powerful tool for exploring the physiological and pathological roles of Cys in complex biological systems.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113142"},"PeriodicalIF":4.2,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144907132","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 : 2025-08-27DOI: 10.1016/j.dyepig.2025.113191
Ruiqi Ren , Mingyu Tian , Jiaxing Li , Xiaomei Yan , Tianyu Liang , Chengyan Wu , Yang Li , Lijun Tang , Keli Zhong
{"title":"Eco-friendly NIR fluorescent probe based on xanthene derivatives for ultrafast detection of sulfites in food samples and biological systems","authors":"Ruiqi Ren , Mingyu Tian , Jiaxing Li , Xiaomei Yan , Tianyu Liang , Chengyan Wu , Yang Li , Lijun Tang , Keli Zhong","doi":"10.1016/j.dyepig.2025.113191","DOIUrl":"10.1016/j.dyepig.2025.113191","url":null,"abstract":"<div><div>Excessive intake of SO<sub>2</sub> and its derivatives in food and environment poses serious threats to human health. Fluorescent molecular imaging probes for the specific detection of sulfites are hindered by poor solubility, which affects the sensitivity to sulfites and limits the range of applications. Here, we developed an eco-friendly near-infrared fluorescent probe <strong>XQD-H</strong>, by constructing a distinctive “Dual-Positive-Ion” platform to address the above challenges. The typical acceptor-π-acceptor (A−π−A) structure puts <strong>XQD-H</strong> fluorescence in the dark state, and its specific combination with HSO<sub>3</sub><sup>−</sup> rapidly transforms from the A−π−A type to the donor-π-acceptor (D−π−A) type to achieve significant fluorescence release. Notably, <strong>XQD-H</strong> showed excellent optical properties for HSO<sub>3</sub><sup>−</sup> in aqueous solution, possessing the advantages of ultra-rapid response, high sensitivity, low detection limits, strong resistance to interference and a wide pH range of applicability. In addition, the detection of HSO<sub>3</sub><sup>−</sup> by the probe <strong>XQD-H</strong> can also be observed with the naked eye under visible light, offering an easy and intuitive method for detection. The <strong>XQD-H</strong> has been successfully used for rapid quantitative detection of sulfites in food, water samples and cellular mitochondria. Thus, this cost-effective, rapid-response, and nondestructive portable device presents a promising platform for real-time sulfite detection and make anti-counterfeiting inks.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113191"},"PeriodicalIF":4.2,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144913775","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 : 2025-08-27DOI: 10.1016/j.dyepig.2025.113188
Kaliyan Prabakaran, Ramalingam Manivannan, Hyunseo Kim, Young-A Son
{"title":"Red emission dyes stability, photoaging study and suitability towards ink application in various substrate","authors":"Kaliyan Prabakaran, Ramalingam Manivannan, Hyunseo Kim, Young-A Son","doi":"10.1016/j.dyepig.2025.113188","DOIUrl":"10.1016/j.dyepig.2025.113188","url":null,"abstract":"<div><div>Red emissive dyes with xanthene core have been developed (<strong>D1-5</strong>) and were characterized using NMR and HRMS spectral analysis. The prepared dyes showed absorption in solution and solid states at the red region. The photoaging studies were performed to measure the stability of the prepared dyes. The photoaging effect of these dyes was verified exceptionally by exposing them to a very strong beam of UV light. The fluorophore <strong>D1</strong> showed better stability, with minimal intensity loss of less than 5 % in absorbance and fluorescence methods. Thermal stability was assessed using TGA, DSC, and XRD measurements. Further, the dyes were formulated for ink application and used to paint in different substrates. The substrates were subjected to photoaging tests under UV light, and their color strength was measured with a data color tool and surface morphology using SEM analysis. FT-IR spectroscopy was used to confirm the surface changes during UV light radiation.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113188"},"PeriodicalIF":4.2,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144913778","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 : 2025-08-27DOI: 10.1016/j.dyepig.2025.113181
Sergio Serrano-Buitrago , Ruth Prieto-Montero , Josué Jiménez , Florencio Moreno , Beatriz L. Maroto , Virginia Martínez-Martínez , Jorge Bañuelos , Santiago de la Moya
{"title":"All-orthogonal BINOLated BODIPY dimers: A synergistic strategy for advancing heavy-metal-free triplet photosensitizers","authors":"Sergio Serrano-Buitrago , Ruth Prieto-Montero , Josué Jiménez , Florencio Moreno , Beatriz L. Maroto , Virginia Martínez-Martínez , Jorge Bañuelos , Santiago de la Moya","doi":"10.1016/j.dyepig.2025.113181","DOIUrl":"10.1016/j.dyepig.2025.113181","url":null,"abstract":"<div><div>Covalently linked organic multichromophores are promising photoactive molecular scaffolds for developing valuable heavy-metal-free triplet photosensitizers. Among them, orthogonally connected BODIPY dimers and easily accessible at-boron BINOLated BODIPYs stand out owing to their efficient oxygen photosensitization, without the need for potentially toxic heavy atoms. In both approaches, the key photophysical mechanism enabling triplet state population involves a photoinduced intramolecular charge transfer by symmetry breaking in the orthogonally connected BODIPY dimers, or by electronic push-pull effect in the BINOL-BODIPY dyads. However, the potential synergistic effect of combining both strategies within a single molecular architecture remains unexplored. This work presents the first systematic study on the impact of integrating both photosensitizing approaches within a single BODIPY-based molecular framework. Our findings demonstrate that easy at-boron 3,3′-dibromoBINOLation serves as an effective chemical strategy to enhance triplet-based photosensitizing performance, without relying on potentially toxic heavy atoms such as transition metals. These results are expected to lay the foundations for the rational design of next-generation of low-cost BODIPY-based triplet photosensitizers for applications beyond heavy-metal-free photodynamic therapy, such as photocatalysis.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113181"},"PeriodicalIF":4.2,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144907291","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 of dual-emission carbon quantum dots for ratiometric fluorescence detection of tartrazine","authors":"Zurong Chen, Yingtao Peng, Shuheng Liu, Xingyu Wang, Yongming Guo","doi":"10.1016/j.dyepig.2025.113189","DOIUrl":"10.1016/j.dyepig.2025.113189","url":null,"abstract":"<div><div>Tartrazine is widely utilized in food and pharmaceutical industries. Long-term excessive intake of tartrazine may cause severe health issues, which underscores the great significance of rapid and accurate detection of tartrazine. In the study, dual-emission CQDs (DE-CQDs) were synthesized <em>via</em> one-pot hydrothermal method using sodium citrate, Rose Bengal, and diethylenetriamine at 180 °C. The as-prepared DE-CQDs exhibited dual emission peaks centered at 435 nm and 520 nm under excitation at 330 nm, along with excellent stability in high concentration of NaCl solutions and good photostability. Notably, the introduction of tartrazine induced significant fluorescence quenching at 435 nm, while causing a slow decrease in fluorescence intensity at 520 nm. This distinct response enabled the development of a highly sensitive ratiometric fluorescence sensor for tartrazine detection. The sensor achieved a wide linear detection range of 0–200 μM with an impressive limit of detection of 0.10 μM. Furthermore, the practical application of this sensing platform was successfully validated through real sample analysis, yielding satisfactory recoveries.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113189"},"PeriodicalIF":4.2,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144917552","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 : 2025-08-26DOI: 10.1016/j.dyepig.2025.113178
Kaili Yang , Min Li , Danqing Wu , Xu Yang , Nian Liu , Jing-Yuan Ge , Zhongyan Chen , Xiangchao Shi , Yan Zhang
{"title":"Conjugation-regulated responsive performance: rapidly urine-excreted fluorescent probes for dual-response detection of SO2 and viscosity and their bioimaging applications","authors":"Kaili Yang , Min Li , Danqing Wu , Xu Yang , Nian Liu , Jing-Yuan Ge , Zhongyan Chen , Xiangchao Shi , Yan Zhang","doi":"10.1016/j.dyepig.2025.113178","DOIUrl":"10.1016/j.dyepig.2025.113178","url":null,"abstract":"<div><div>Sulfur dioxide (SO<sub>2</sub>) concentration and viscosity levels within living organisms are closely associated with various physiological and pathological processes. The development of novel fluorescent probes enabling simultaneous detection of SO<sub>2</sub> and viscosity is crucial for advancing disease research. Herein, we synthesized two novel fluorescent probes (<strong>CyAN-1</strong> and <strong>CyAN-2</strong>) featuring dual SO<sub>2</sub>/viscosity responsiveness. These probes integrate an electron-withdrawing benzindolizine hemicyanine moiety and an electron-donating <em>N</em>, <em>N</em>-dimethylaniline unit, connected through carbon-carbon double bonds of differential conjugation lengths. This molecular architecture facilitates rapid SO<sub>2</sub> detection via Michael addition while enabling sensitive viscosity response through a restricted rotation mechanism. <strong>CyAN-1</strong> exhibited a remarkable 300-fold fluorescence enhancement at 475 nm toward SO<sub>2</sub>, while maintaining high sensitivity (86 nM) and rapid response (180 s) in aqueous media. Moreover, its fluorescence signal at 628 nm displays sensitive viscosity-dependent behavior across a broad range from 0.6 cP to 623.4 cP. Confocal fluorescence imaging indicated that <strong>CyAN-1</strong> exhibits excellent lysosomal targeting capacity, enabling real-time visualization of exogenous/endogenous SO<sub>2</sub> and dynamic monitoring of lipopolysaccharide (LPS)-induced viscosity changes in HeLa cells. Moreover, <strong>CyAN-1</strong> was employed to image viscosity abnormalities in inflammation, tumor and non-alcoholic steatohepatitis (NASH) model mice. Notably, it exhibits rapid urinary excretion following intravenous administration, thereby minimizing potential toxicity from prolonged retention of metabolites in organs. We envision <strong>CyAN-1</strong> as a promising molecular probe for elucidating pathophysiological processes through simultaneous tracking of SO<sub>2</sub> and viscosity.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113178"},"PeriodicalIF":4.2,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144907289","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 : 2025-08-26DOI: 10.1016/j.dyepig.2025.113169
Ruimin Chen, Qinglong Zhang, Chun Liu
{"title":"AIPE-active cationic Ru(II) complexes for detecting picric acid in aqueous media","authors":"Ruimin Chen, Qinglong Zhang, Chun Liu","doi":"10.1016/j.dyepig.2025.113169","DOIUrl":"10.1016/j.dyepig.2025.113169","url":null,"abstract":"<div><div>Three cationic Ru(II) complexes, <strong>Ru1</strong>–<strong>Ru3</strong>, were designed and synthesized by introducing a phenyl (Ph), diphenylamino (DPA), and 4-(diphenylamino)phenyl (TPA) group to two 2,2′-bipyridine ligands, respectively. All complexes were fully characterized. <strong>Ru1</strong>–<strong>Ru3</strong> exhibit aggregation-induced phosphorescent emission (AIPE) properties in THF/H<sub>2</sub>O. <strong>Ru1</strong> containing the Ph group and <strong>Ru2</strong> containing the DPA group exhibit maximum emission intensity at a 70% water fraction, showing 2.25-fold and 2.28-fold enhancement compared to those in THF, respectively. Notably, <strong>Ru3</strong> incorporating the TPA group demonstrates the highest AIPE activity. The emission intensity of <strong>Ru3</strong> in THF/H<sub>2</sub>O at a 90% water fraction increases to 4.01-fold of that in THF solution. Utilizing the AIPE properties of <strong>Ru1</strong>–<strong>Ru3</strong>, the detection of picric acid (PA) in aqueous media was successfully achieved. Moreover, <strong>Ru1</strong>–<strong>Ru3</strong> exhibit highly selective and sensitive detection of PA even in the presence of various interfering substances, including nitroaromatic, phenolic, and ionic compounds. Among them, <strong>Ru3</strong> possesses the highest sensitivity (<em>K</em><sub>SV</sub> = 9.4 × 10<sup>4</sup> M<sup>−1</sup>) and the lowest limit of detection (LOD = 23 nM). The mechanism of <strong>Ru1</strong>–<strong>Ru3</strong> as the probes for detecting PA is photoinduced electron transfer.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113169"},"PeriodicalIF":4.2,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144907290","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 : 2025-08-25DOI: 10.1016/j.dyepig.2025.113177
Cheng-Zhen Yuan , Yi-Chen Ou , Yu-Jui Pan , Shao-An Hua , Hsiu-Wen Chien
{"title":"Multifunctional poly(sulfobetaine acrylamide) hydrogel integrating robust mechanical properties, pH-triggered multicolor fluorescence, and antibacterial efficacy","authors":"Cheng-Zhen Yuan , Yi-Chen Ou , Yu-Jui Pan , Shao-An Hua , Hsiu-Wen Chien","doi":"10.1016/j.dyepig.2025.113177","DOIUrl":"10.1016/j.dyepig.2025.113177","url":null,"abstract":"<div><div>This study reports the development of a multicolor fluorescence zwitterionic hydrophobic association hydrogel based on sulfobetaine acrylamide (SBAA) for advanced wound care applications. Initially, the mechanical properties and self-healing capabilities of hydrophobically associated poly(sulfobetaine methacrylate) (polySBMA) and polySBAA hydrogels were systematically compared. Owing to the presence of amide bonds in SBAA, which promote additional hydrogen bonding interactions, the polySBAA hydrogel exhibited significantly improved mechanical strength, fatigue resistance, and self-healing efficiency—achieving nearly 100 % recovery within 90 s, compared to approximately 75 % for polySBMA. Next, tris(2,6-pyridinedicarboxylato)lanthanide(III) complexes (Ln(PDAc)<sub>3</sub>) were incorporated into the hydrogel matrix. By adjusting the Eu(PDAc)<sub>3</sub>/Tb(PDAc)<sub>3</sub> ratio, the hydrogel exhibited tunable multicolor fluorescence. Furthermore, pH-responsive fluorescence behavior was achieved through the protonation–deprotonation equilibrium of PDAc ligands under varying pH conditions. In the physiologically relevant pH range of 5.5–8.0, the hydrogel demonstrated distinct fluorescence changes, allowing for intuitive and real-time monitoring of bacterial contamination. In addition, ciprofloxacin (CIP) was loaded into the hydrogel to impart antimicrobial functionality. Inhibition zone assays confirmed strong bactericidal activity against <em>E. coli</em> and <em>S. aureus</em>, which was further validated using an ex vivo infected pig skin model. Overall, the engineered hydrogel integrates enhanced mechanical properties, rapid self-healing, pH-responsive fluorescent sensing, and potent antibacterial efficacy, highlighting its potential as a smart wound dressing capable of simultaneous infection diagnosis and treatment.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113177"},"PeriodicalIF":4.2,"publicationDate":"2025-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144907134","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 : 2025-08-23DOI: 10.1016/j.dyepig.2025.113166
Lihan Chen , Huihui Liang , Pei Wang , Huiyu Si , Youhui Zhang , Xin Lai , Honglong Zou , Kexin Zhou , Guodong Xu , Yonggui Song , Xin Zhou , Xunfan Liao
{"title":"A large π-conjugated organic photothermal agent for photoacoustic-guided photothermal therapy","authors":"Lihan Chen , Huihui Liang , Pei Wang , Huiyu Si , Youhui Zhang , Xin Lai , Honglong Zou , Kexin Zhou , Guodong Xu , Yonggui Song , Xin Zhou , Xunfan Liao","doi":"10.1016/j.dyepig.2025.113166","DOIUrl":"10.1016/j.dyepig.2025.113166","url":null,"abstract":"<div><div>Multimodal imaging-guided combinational phototherapies triggered by a single near-infrared (NIR) photothermal agent are promising approach for the treatment of breast cancer. However, the bottleneck is lack of stable photothermal materials with NIR absorption and high photothermal conversion efficiency (PCE). Herein, we have developed a novel π-conjugated skeleton organic photothermal agent (DTPC-DFIC) with strong NIR absorption in the region from 770 to 1000 nm. The nanoparticles of DTPC-DFIC (DTPC-DFIC NPs) encapsulated with amphiphilic DSPE-mPEG2000 by nanoprecipitation method, can be used for photoacoustic imaging-guided photothermal therapy (PTT). Notably, DTPC-DFIC NPs shown good biocompatibility, photostability and a high photothermal conversion efficiency up to 72.3 %. In vivo and in vitro experiments confirmed that the DTPC-DFIC NPs have an excellent biosafety and an efficient anti-tumor effect. Overall, this work not only proposes a promising large π-conjugated skeleton organic photothermal agent but also provides insight into developing highly efficient nanomaterials for cancer theranostics.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113166"},"PeriodicalIF":4.2,"publicationDate":"2025-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144892767","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 : 2025-08-23DOI: 10.1016/j.dyepig.2025.113161
Ahmad Kassem , Darío Puchán Sánchez , Karolina Saczuk , Arthur H.G. David , Magali Allain , Marco Deiana , Julien Boixel , Gregory C. Welch , Cyrille Monnereau , Pierre Josse , Clément Cabanetos
{"title":"Orientation of nitration in bay-region of benzothioxanthene imide: A streamlined pathway to N- and S-annulated derivatives","authors":"Ahmad Kassem , Darío Puchán Sánchez , Karolina Saczuk , Arthur H.G. David , Magali Allain , Marco Deiana , Julien Boixel , Gregory C. Welch , Cyrille Monnereau , Pierre Josse , Clément Cabanetos","doi":"10.1016/j.dyepig.2025.113161","DOIUrl":"10.1016/j.dyepig.2025.113161","url":null,"abstract":"<div><div><em>N</em>-annulation has recently emerged as a powerful approach for modulating the optoelectronic properties of benzothioxanthene imide (BTI) derivatives, enabling their application in areas ranging from light-emitting devices to photodynamic therapy. In this study, we report an optimized synthetic strategy that reduces the original seven-step process for <em>N</em>-annulated BTIs to just four steps, achieving a ∼40 % improvement in efficiency. Additionally, we introduce a novel <em>S</em>-annulated BTI derivative, extending the scope of heteroatom-involving ring fusion. Comparative analysis between <em>N</em>- and <em>S</em>-annulated compounds reveals the pronounced influence of a single-atom modification on the π-conjugated system. These findings demonstrate the utility of annulation as a chemically accessible and versatile tool for fine-tuning molecular architectures with tailored photophysical properties.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"244 ","pages":"Article 113161"},"PeriodicalIF":4.2,"publicationDate":"2025-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144892856","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}