The role of steric hindrance in the intramolecular oxidative aromatic coupling of pyrrolo[3, 2-b]pyrroles. Issue 77 (5th September 2016)

• Record Type: Journal Article
• Authors: Krzeszewski, Maciej; Świder, Paweł; Dobrzycki, Łukasz; Cyrański, Michał K.; Danikiewicz, Witold; Gryko, Daniel T.
• Is Part Of: Chemical communications. Volume 52:Issue 77(2016)
• Page Start: 11539
• Page End: 11542
• Publication Date: 2016-09-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc05904j
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Sterically hindered tetraaryl-pyrrolo[3, 2- b ]pyrroles undergo oxidative aromatic coupling, forming a fluorene scaffold linked via a spiro carbon atom with a novel π-conjugated scaffold. Abstract : The presence of steric hindrance triggers different reaction pathways in the intramolecular oxidative aromatic coupling of tetraaryl-pyrrolo[3, 2- b ]pyrroles and leads to the formation of a fluorene moiety and a new cationic π-system linked together by a spiro carbon atom. Computational studies elegantly rationalized these results. These previously unknown functional dyes emit red light with reasonable efficiency.