Chang-Seok Hyun , Joohwan Eo , Ji Eon Kwon , Byeong-Kwan An
{"title":"1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization","authors":"Chang-Seok Hyun , Joohwan Eo , Ji Eon Kwon , Byeong-Kwan An","doi":"10.1080/00397911.2024.2381074","DOIUrl":null,"url":null,"abstract":"<div><p>1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and <em>tris</em>(THAO)-TT, were synthesized by Diels–Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and <em>tris</em>(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and <em>tris</em>(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":1.8000,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000705","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and tris(THAO)-TT, were synthesized by Diels–Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and tris(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and tris(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.
期刊介绍:
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.