{"title":"合理设计的双吡咯烷基色团的 pH 响应超分子开关","authors":"Debasish Mandal, Abani Sarkar, Kanhu Charan Behera, Mangalampalli Ravikanth","doi":"10.1039/d4sc07016j","DOIUrl":null,"url":null,"abstract":"Herein, we present a strategy to access a novel class of pH-responsive, dual-state emissive (DSE), highly fluorescent pyrrole-based chromophores via diformylation of dipyrroethenes (DPE) followed by condensation with various anilines derivatives. The DPE-based chromophores exhibit a large Stokes’ shift and maintain good fluorescent quantum yields. Remarkably, these chromophores demonstrate reversible colourimetric changes and a fluorometric 'on-off-on' switch in response to pH variations. Various spectroscopic techniques, optical microscopy, X-ray crystallography, and computational studies revealed that the synthesized molecules adopt a two-dimensional conformation due to the presence of strong π···π stacking and hydrogen bonding interactions, allowing them to function as flexible molecular hosts. Under acidic conditions, selective protonation of imine bonds and subsequent complexation with counter anion enhance the host-guest interactions, resulting in a stable three-dimensional supramolecular structure. Notably, the reversibility of these molecules under basic conditions showcases the robustness and potential applications of these chromophores in various fields, ranging from the design of finely tuned pH-responsive degradable polymers to self-healing materials, sensing, and molecular devices.","PeriodicalId":9909,"journal":{"name":"Chemical Science","volume":"3 1","pages":""},"PeriodicalIF":7.6000,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"pH-Responsive Supramolecular Switch of Rationally Designed Dipyrroethene-Based Chromophore\",\"authors\":\"Debasish Mandal, Abani Sarkar, Kanhu Charan Behera, Mangalampalli Ravikanth\",\"doi\":\"10.1039/d4sc07016j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we present a strategy to access a novel class of pH-responsive, dual-state emissive (DSE), highly fluorescent pyrrole-based chromophores via diformylation of dipyrroethenes (DPE) followed by condensation with various anilines derivatives. The DPE-based chromophores exhibit a large Stokes’ shift and maintain good fluorescent quantum yields. Remarkably, these chromophores demonstrate reversible colourimetric changes and a fluorometric 'on-off-on' switch in response to pH variations. Various spectroscopic techniques, optical microscopy, X-ray crystallography, and computational studies revealed that the synthesized molecules adopt a two-dimensional conformation due to the presence of strong π···π stacking and hydrogen bonding interactions, allowing them to function as flexible molecular hosts. Under acidic conditions, selective protonation of imine bonds and subsequent complexation with counter anion enhance the host-guest interactions, resulting in a stable three-dimensional supramolecular structure. Notably, the reversibility of these molecules under basic conditions showcases the robustness and potential applications of these chromophores in various fields, ranging from the design of finely tuned pH-responsive degradable polymers to self-healing materials, sensing, and molecular devices.\",\"PeriodicalId\":9909,\"journal\":{\"name\":\"Chemical Science\",\"volume\":\"3 1\",\"pages\":\"\"},\"PeriodicalIF\":7.6000,\"publicationDate\":\"2024-12-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Science\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4sc07016j\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Science","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4sc07016j","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
pH-Responsive Supramolecular Switch of Rationally Designed Dipyrroethene-Based Chromophore
Herein, we present a strategy to access a novel class of pH-responsive, dual-state emissive (DSE), highly fluorescent pyrrole-based chromophores via diformylation of dipyrroethenes (DPE) followed by condensation with various anilines derivatives. The DPE-based chromophores exhibit a large Stokes’ shift and maintain good fluorescent quantum yields. Remarkably, these chromophores demonstrate reversible colourimetric changes and a fluorometric 'on-off-on' switch in response to pH variations. Various spectroscopic techniques, optical microscopy, X-ray crystallography, and computational studies revealed that the synthesized molecules adopt a two-dimensional conformation due to the presence of strong π···π stacking and hydrogen bonding interactions, allowing them to function as flexible molecular hosts. Under acidic conditions, selective protonation of imine bonds and subsequent complexation with counter anion enhance the host-guest interactions, resulting in a stable three-dimensional supramolecular structure. Notably, the reversibility of these molecules under basic conditions showcases the robustness and potential applications of these chromophores in various fields, ranging from the design of finely tuned pH-responsive degradable polymers to self-healing materials, sensing, and molecular devices.
期刊介绍:
Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.