{"title":"Orthogonally Arranged π-Electronic Systems with Anion-Responsive Moiety Exhibiting Photoinduced Electron Transfer.","authors":"Ryuto Toyoshima,Hiroki Horita,Shiori Tsuda,Shunsuke Kobashi,Hiroto Kobayashi,Yoichi Kobayashi,Hiromitsu Maeda","doi":"10.1021/acs.orglett.5c02265","DOIUrl":null,"url":null,"abstract":"Orthogonally arranged π-electronic systems comprising directly connected electron-deficient and anion-responsive moieties were synthesized by the connection of acridine/N-methylacridinium and dipyrrolylpyrimidine (dpp) units. Acridine- and N-methylacridinium-substituted dpps showed anion-binding behaviors via hydrogen bonding at pyrrole NH and pyrimidine CH, suggesting the possibility of modulating the electronic states of the anion-responsive π-electronic systems. Transient absorption measurements of the acridine-substituted dpp revealed a photoinduced electron transfer from the anion-responsive unit to the electron-deficient moiety, which was accelerated by anion binding.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"109 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c02265","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Orthogonally arranged π-electronic systems comprising directly connected electron-deficient and anion-responsive moieties were synthesized by the connection of acridine/N-methylacridinium and dipyrrolylpyrimidine (dpp) units. Acridine- and N-methylacridinium-substituted dpps showed anion-binding behaviors via hydrogen bonding at pyrrole NH and pyrimidine CH, suggesting the possibility of modulating the electronic states of the anion-responsive π-electronic systems. Transient absorption measurements of the acridine-substituted dpp revealed a photoinduced electron transfer from the anion-responsive unit to the electron-deficient moiety, which was accelerated by anion binding.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.