{"title":"Homochiral Self-Sorting During Macrocycle Formation and their Chiroptical Properties.","authors":"Diptiprava Sahoo, Soumen De","doi":"10.1002/open.202400400","DOIUrl":null,"url":null,"abstract":"<p><p>Several BINOL-derived C2-symmetric aldehydes were synthesized to investigate chiral self-sorting phenomena during macrocycle formation in the presence of aliphatic and aromatic bisamines. While self-sorting was unsuccessful with aliphatic amines, aromatic amine dictated complete homochiral self-sorting, confirmed by <sup>1</sup>H NMR analysis and molecular modelling. Additionally, the impact of macrocyclization on the chiroptical properties of these macrocycles was examined. The Cotton effects band red-shifted for aromatic amines owing to extended conjugation. Notably, a substantial increase in specific rotation was observed upon macrocycle formation.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e202400400"},"PeriodicalIF":2.5000,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemistryOpen","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/open.202400400","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Several BINOL-derived C2-symmetric aldehydes were synthesized to investigate chiral self-sorting phenomena during macrocycle formation in the presence of aliphatic and aromatic bisamines. While self-sorting was unsuccessful with aliphatic amines, aromatic amine dictated complete homochiral self-sorting, confirmed by 1H NMR analysis and molecular modelling. Additionally, the impact of macrocyclization on the chiroptical properties of these macrocycles was examined. The Cotton effects band red-shifted for aromatic amines owing to extended conjugation. Notably, a substantial increase in specific rotation was observed upon macrocycle formation.
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