Dyes and Pigments最新文献

{"title":"Theoretical investigation of the structure-property relationships of [n]benzocyclobutadiene carbon nanobelt: Aromaticity, singlet fission, and (hyper)polarizability","authors":"Qing Li ,&nbsp;Lingyi Meng ,&nbsp;Luyao Liu ,&nbsp;Ziang Nan ,&nbsp;Zhu Zhuo ,&nbsp;Wei Wang ,&nbsp;Yougui Huang","doi":"10.1016/j.dyepig.2024.112549","DOIUrl":"10.1016/j.dyepig.2024.112549","url":null,"abstract":"<div><div>We present a theoretical design for a series of multifunctional nanomaterials that exhibit superior performance in singlet fission (SF) as well as exceptional nonlinear optical (NLO) performance. Our study focuses on a systematic investigation into the aromaticity, diradical character, excited state transition and (hyper)polarizability of the [n]benzocyclobutadiene carbon nanobelt system. To provide further guidance for designing multifunctional nanomaterials, our quantum chemical calculations propose empirical rules regarding the influence of aromatics on SF and NLO: Through an exploration of SF properties, we observed significant diradical character with radical sites exclusively located at anti-aromatic positions. Furthermore, these anti-aromatic positions serve as transition sites for excited state transitions to achieve the necessary low triplet excited states energy for SF. Then, by conducting calculations on NLO properties, we ascertain that the main tensor components of first-order hyperpolarizability (<em>β</em>_total) and second-order hyperpolarizability (<em>γ</em>_total) come from the anti-aromatic region. However, there exists a contrasting impact of anti-aromaticity on first- and second-order hyperpolarizability density. The positive and negative contributions to first-order hyperpolarizability density mainly come from both aromatic and anti-aromatic regions while for second-order hyperpolarizability density it is contradictory. This study elucidates the role of aromatic sites in multifunctional nanomaterials with respect to diradical sites, excited state transition regions, and (hyper)polarizability density distribution.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"234 ","pages":"Article 112549"},"PeriodicalIF":4.1,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142698291","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":"A highly selective ESIPT-mechanism-based, ratiometric fluorescent sensor for zinc ions","authors":"Miloš Jović ,&nbsp;Olivera Marković ,&nbsp;Timothy R. Newhouse ,&nbsp;Igor M. Opsenica ,&nbsp;Života Selaković","doi":"10.1016/j.dyepig.2024.112547","DOIUrl":"10.1016/j.dyepig.2024.112547","url":null,"abstract":"<div><div>Zinc is crucial for human health, a fact that has prompted interest in developing efficient fluorescent probes for its detection. Traditional approaches, however, face issues such as environmental interference and limited selectivity. This has led to research focusing on ratiometric sensing and making use of the excited-state intramolecular proton transfer (ESIPT) effect. Tetramic acid and its 4-methoxy analogue are significant structural motifs in many natural products from various organisms, including those which can bind metal ions, such as zinc. This study presents a new ratiometric fluorescent sensor for zinc that leverages ESIPT for high selectivity and efficacy, and combines tetramic acid and pyridine substructures. Our probe exhibits a strong emission band at 515 nm upon excitation in polar aprotic solvents, and upon excitation at 360 nm a selective ratiometric response to Zn²⁺ in acetonitrile, with distinct, blue-shifted emission maximum at 460 nm. This is accompanied by a color change from green to turquoise, which is visible to the unaided eye under a UV lamp. Our sensor shows excellent sensitivity, which is confirmed by a low detection limit of 1.26 × 10⁻⁶ M. The binding of the compounds to Zn²⁺ ions was further confirmed in an NMR study, and the effects of common anions and change in pH were also examined. The overall simplicity of our structure, alongside its unique properties and open possibilities for structural modifications, makes it attractive for further research.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"234 ","pages":"Article 112547"},"PeriodicalIF":4.1,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142698924","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":"Single/dual/multi-responsive fluorescent probes for multiple analytes in mitophagy: A review","authors":"Sha Li,&nbsp;Zhiying Li,&nbsp;Miao Yan,&nbsp;Haixian Ren","doi":"10.1016/j.dyepig.2024.112545","DOIUrl":"10.1016/j.dyepig.2024.112545","url":null,"abstract":"<div><div>As the \"power stations\" of the cell, mitochondria are involved in many energy metabolism processes. Abnormalities in mitochondrial structure and function (mitophagy) can affect the activity of living cells and lead to disease. Visualizing the concentration changes in the relevant analytes in real time is essential to better understand the visualization of mitophagy processes. Several probes have been reported for the detection of one or more analytes in mitochondria. However, topic has not been summarized. Therefore, it is very important to explore the latest progress of small molecule fluorescent probes in this emerging field. Based on the role of analytes in mitochondrial autophagy, this reviews recent advances in single/double/multi-responsive fluorescent probes with specific recognition function and selective signal conversion of mitochondrial autophagy related analytes (including pH, viscosity, polarity, hypoxia, and mitochondrial ROS RSS fluctuations) since 2016. We believe that this review will be of wide interest to scientists engaged in research related to mitochondrial autophagy and provide valuable insights to chemists, biologists and medical researchers to contribute to the diagnosis and treatment of related diseases.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"234 ","pages":"Article 112545"},"PeriodicalIF":4.1,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699137","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":"Preparation of photochromic microcapsules with a diarylethene and polyurethane/chitosan for smart textiles","authors":"Jie Hu ,&nbsp;Hengju Zhou ,&nbsp;Xinyao Wang ,&nbsp;Shiqiang Cui ,&nbsp;Shouzhi Pu","doi":"10.1016/j.dyepig.2024.112546","DOIUrl":"10.1016/j.dyepig.2024.112546","url":null,"abstract":"<div><div>In order to overcome the influences of external environment on the properties photochromic compounds and expend their applications fields, various photochromic microcapsules have been prepared. However, the effects of wall materials on the properties of photochromic compounds need to be further studied. In this study, two photochromic microcapsules were prepared with polyurethane/chitosan as wall materials and a diarylethene molecular as core material. The properties such as photochromism, fatigue resistance, the sealing, and thermal stability of the microcapsules were studied, and the effects of the wall materials on the photochromic properties of the diarylethene were also investigated. Furthermore, the prepared microcapsules have been successfully applied to cotton fabrics of photochromic smart textiles.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"234 ","pages":"Article 112546"},"PeriodicalIF":4.1,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142698923","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":"Characterization of photophysical and electrochemical properties of a PNDT-T-DPP dye-based polymer with highly planar features and development of organic electronic applications","authors":"Jinyang Chen ,&nbsp;Yue Zhao ,&nbsp;Wenxiang Zeng ,&nbsp;PingPing Ni ,&nbsp;Yujie Wang ,&nbsp;Shuchang Chen ,&nbsp;Xianhe Yuan ,&nbsp;Zhuowen Feng ,&nbsp;Suhong Tang ,&nbsp;Sichun Wang ,&nbsp;Shiwei Ren ,&nbsp;Abderrahim Yassar","doi":"10.1016/j.dyepig.2024.112536","DOIUrl":"10.1016/j.dyepig.2024.112536","url":null,"abstract":"<div><div>Common organic small molecule dyes exhibit chemical modifiability and are easy to polymerize, making them potential monomers in organic electronics. The multifunctionality of organic synthetic chemistry allows for material adaptability. Here, we report the synthesis route and purification methods for dye polymer based on thiophene-diketopyrrolopyrrole. Their orderly conjugated structure and high coplanarity contribute to a high crystallinity, which is favorable for charge carrier transport. By adjusting the device structure and thin film preparation conditions, the hole transport properties of the materials were further optimized, achieving a maximum mobility of up to 0.35 cm² V⁻¹ s⁻¹. The excellent charge carrier performance reveals the potential of such material for applications in organic electronics.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"234 ","pages":"Article 112536"},"PeriodicalIF":4.1,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142698925","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":"A ratiometric fluorescent probe based on FRET mechanism for pH and its cell imaging","authors":"Zhen-Ming Yue ,&nbsp;Shu-Mei Zhai ,&nbsp;Bing-Yu Wei ,&nbsp;Bao-Xiang Zhao ,&nbsp;Zhao-Min Lin","doi":"10.1016/j.dyepig.2024.112544","DOIUrl":"10.1016/j.dyepig.2024.112544","url":null,"abstract":"<div><div>pH balance is a prerequisite for maintaining cell function optimally and performs an important role in diverse physiological activities. Even subtle changes in cellular pH can influence many cell behaviors. More specifically, for mitochondria, its unique functions under physiological conditions depend largely on its pH values. Therefore, an effective analytical method needs to be developed to detect the alteration of intracellular pH values, especial in mitochondria. In this work, a ratiometric pH fluorescent probe (<strong>DPM</strong>) based on fluorescence resonance energy transfer (FRET) mechanism was developed by constructing coumarin and hemicyanine fluorophore. <strong>DPM</strong> could respond to pH changes by the FRET-off and FRET-on process depending on the cyclization and ring-opening reaction. <strong>DPM</strong> exhibited high energy transfer efficiency (89.1 %) and responded to pH ranges of 6.0–8.0 rapidly and selectively (pKa value of 7.6 in solution and 7.0 in cells). Moreover, <strong>DPM</strong> exhibited nearly non-toxicity to living cells and excellent photostability. <strong>DPM</strong> showed great pH-responsive feature in cells and achieved detection of mitochondrial acidification. The present work not only provided a new structure for pH fluorescence probe and simple synthetic method for the FRET-based probe but also found that the probe could target mitochondria in living cells.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112544"},"PeriodicalIF":4.1,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656675","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":"Third-order nonlinear optical properties based on triphenylamine derivative-based covalent organic frameworks","authors":"Jianhong Jia,&nbsp;Mingyan Li,&nbsp;Ran Yao,&nbsp;Jiahui Chu,&nbsp;Endian Su,&nbsp;Xiangxiang Zhou,&nbsp;Yanhong Cui,&nbsp;Yuanbin She","doi":"10.1016/j.dyepig.2024.112542","DOIUrl":"10.1016/j.dyepig.2024.112542","url":null,"abstract":"<div><div>Nonlinear optics (NLO) is an extremely critical research area. In recent years, covalent organic frameworks (COFs) have attracted much attention as a potential NLO material. In this study, a series of COF materials with different D-A effects were successfully synthesized based on the excellent electron-donating properties of the triphenylamine group and were prepared into D-A COFsKBr sheet materials that can be used for third-order NLO by the KBr−pressing method. The results of the open-aperture Z-scan technique showed that all COFsKBr sheets exhibited saturable absorption (SA) behavior at 3 μJ, with nonlinear absorption coefficients (<em>β</em>) of −1.64, −1.23, and −2.02 × 10⁻⁹ mW⁻¹ for <strong>PT-PA</strong>, <strong>PT-BD</strong>, and <strong>PT-TZ</strong>, respectively. Theoretical calculations show that the electron transport distance of <strong>PT-PA</strong> is shorter than that of <strong>PT-BD</strong>, while the introduction of S atoms makes the D-A effect of <strong>PT-TZ</strong> stronger than that of <strong>PT-BD</strong>, and thus the SA properties of <strong>PT-PA</strong> and <strong>PT-TZ</strong> are better than those of <strong>PT-BD</strong>. These works indicate that the COFsKBr sheets have a potential application as high-performance NLO materials and also provide an option for COFs powder application in the field of third-order NLO.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"234 ","pages":"Article 112542"},"PeriodicalIF":4.1,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142698926","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":"Dynamic optical and thermal modulation of electrochromic smart windows and sunglasses based on benzothiadiazole-extended viologen derivatives","authors":"Yu-Zhen Li,&nbsp;Zhi-hao Cui,&nbsp;Dong-yun Jiang,&nbsp;Pu-yang Tang,&nbsp;Cheng-bin Gong,&nbsp;Qian Tang","doi":"10.1016/j.dyepig.2024.112543","DOIUrl":"10.1016/j.dyepig.2024.112543","url":null,"abstract":"<div><div>Smart windows can regulate indoor lighting and heat intensity by isolating external light and heat, thereby achieving the goal of saving building energy consumption. However, traditional smart windows require additional power consumption to adjust color changes and thus regulate transmittance, and can only achieve relatively single control of light intensity and heat. Developing smart windows with dynamic photothermal modulation remains challenging. This paper reports two novel benzothiadiazole extended viologen derivatives DBTBB and DBTBH. The carboxymethylcellulose sodium hydrogel-state electrochromic devices based on DBTBB and DBTBH showed good electrochromic performance including a low operating voltage, a rapid response time, a high optical contrast, excellent cycling stability, and a large coloration efficiency. A dynamic photothermal modulation electrochromic smart window self-powered by a small commercial solar panel was constructed using the electrochromic hydrogel based on DBTBB, which could sense the changes in external irradiating light intensity and dynamically adjust the indoor light and heat without additional consumption of electricity, and the adjusting capability increased with the increase of irradiating light intensity. In addition, the application in smart color changing sunglasses self-powered by a solar panel was also investigated, the electrochromic sunglasses showed dynamic transmittance modulation in response to irradiating light intensities with good cycling stability, a gradual change in purple color from light to dark was observed as the irradiating light intensity increased from 105  →  225→415  →  650→920 lux. Moreover, both text and a colored logo were clearly displayed under different irradiating light intensities. This provides new methods for electrochromic applications in commercial settings and improving human quality of life, thereby creating new possibilities in the increasingly intelligent world.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112543"},"PeriodicalIF":4.1,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656680","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":"First oxidative coupling of cyclazine heterocycle via regioselective dimerization of 1,2-dicarbomethoxy-3-phenylcycl[3.2.2]azine: Synthesis, theoretical aspects and physicochemical studies","authors":"Andrei S. Starikov ,&nbsp;Alexey V. Borodachev ,&nbsp;Pavel A. Tarakanov ,&nbsp;Nikita A. Slesarenko ,&nbsp;Sergey V. Simonov ,&nbsp;Anton O. Simakov ,&nbsp;Olga I. Istakova ,&nbsp;Olga A. Goncharova ,&nbsp;Dmitry V. Konev ,&nbsp;Victor E. Pushkarev","doi":"10.1016/j.dyepig.2024.112539","DOIUrl":"10.1016/j.dyepig.2024.112539","url":null,"abstract":"<div><div>The first covalently linked dimer has been prepared for cyclazine systems by regioselective oxidative homocoupling of 1,2-dicarbomethoxy-3-phenylcycl[3.2.2]azine. The regioselectivity of this reaction at 4-position, having been confirmed by X-ray diffraction analysis and NMR spectroscopy, has been also reliably predicted within the model of average local ionization energy on the molecular surface of the starting monomer at the BP86/def2-TZVP level of theory. Due to the planar π-π interaction of the cycl[3.2.2]azine subunits, the dimer is a green fluorophore (λ_em = 527 nm, toluene), characterized by a bathochromic shift of the main bands in the UV–vis and fluorescence spectra relative to the monomer by 41 and 71 nm, respectively. Furthermore, the dimer demonstrates an increased fluorescence quantum yield relative to the monomer (55 % <em>vs.</em> 35 % in toluene), and according to the data of X-ray diffraction analysis, DFT calculations and variable temperature 1D and 2D ¹H NMR spectroscopy, is characterized by hindered rotation of the S₁-state-involved cycl[3.2.2]azine cores along the C4–C4′ bond axis. Such prerequisites determine good application potential of the 4-4′ coupled cycl[3.2.2]azine derivatives as turn-on fluorescent, i.e. fluorogenic probes for advanced bioimaging in living systems. Finally, unlike the monomer, the dimer shows reversibility of both one- and two-electron reduction and oxidation processes, and therefore can become the basis of both n- and p-type semiconductors.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112539"},"PeriodicalIF":4.1,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656678","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":"1-Alkylamino-3H-naphtho[1,2,3-de]quinoline-2,7-diones. Visualization of lipid droplets in living cells","authors":"Sergei A. Chernenko ,&nbsp;Anton L. Shatsauskas ,&nbsp;Yuri V. Shatalin ,&nbsp;Victoria S. Shubina ,&nbsp;Margarita I. Kobyakova ,&nbsp;Tatyana Yu Zheleznova ,&nbsp;Anastasia S. Kostyuchenko ,&nbsp;Alexander S. Fisyuk","doi":"10.1016/j.dyepig.2024.112541","DOIUrl":"10.1016/j.dyepig.2024.112541","url":null,"abstract":"<div><div>A series of previously unknown 1-alkylamino-3<em>H</em>-naphtho[1,2,3-<em>de</em>]quinoline-2,7-diones, 1-alkylamino-6-nitro-3<em>H</em>-naphtho[1,2,3-<em>de</em>]quinoline-2,7-diones, and 1-alkylamino-6-amino-3<em>H</em>-naphtho[1,2,3-<em>de</em>]quinoline-2,7-diones was obtained by nucleophilic substitution of the tosyl group of 1-tosyl-3<em>H</em>-naphtho[1,2,3-<em>de</em>]quinoline-2,7-dione with aliphatic amines. Among the synthesized compounds, fluorophores emitting light from the blue-green to orange-red region of the visible spectrum with fluorescence quantum yields up to 0.39 were found. Some of the synthesized compounds showed phototoxic effects on human breast carcinoma cell line BT474. It was shown that 3-butyl-1-(butylamino)-6-nitronaphthoquinolinedione stains exclusively lipid droplets, has a large Stokes shift and can be used for visualization of these organelles.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112541"},"PeriodicalIF":4.1,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656679","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}