Thia‐Bridged Triarylamine Hetero[4]Helicenes: Regioselective Synthesis and Functionalization. Issue 1 (6th November 2018)

• Record Type: Journal Article
• Authors: Menichetti, Stefano; Faggi, Cristina; Onori, Martina; Piantini, Sara; Ferreira, Misael; Rocchi, Sara; Lupi, Michela; Marin, Ivan; Maggini, Michele; Viglianisi, Caterina
• Is Part Of: European journal of organic chemistry. Issue 1(2019)
• Page Start: 168
• Page End: 175
• Publication Date: 2018-11-06
• Subjects: Helicenes -- Electrophilic aromatic substitution -- Sulfur heterocycles -- Chirality -- Regioselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801493
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Thia‐bridged triarylamine hetero[4]helicenes (TBTH[4]H) are a peculiar class of geometrically stable [4]helicenes that have shown promising applications as organic electronic materials. Their structure comprises a bis‐phenothiazine moiety, with a nitrogen atom and an aromatic ring in common, forced into a helix‐shaped arrangement by four carbon–sulfur bonds. We describe a detailed study on the scope and application of the electrophilic sulfur insertion path to TBTH[4]H, with particular emphasis on the regioselective preparation of asymmetric (not dissymmetric) derivatives. Abstract : The regio‐controlled synthesis of several thia‐bridged triarylamine hetero[4]helicenes (TBTH[4]H), a peculiar class of geometrically stable [4]helicenes, is achieved using triarylamines or N ‐aryl phenothiazines as suitable starting materials. The control of the regiochemistry allows modifications of these peculiar compounds that have promising applications as organic electronic materials.