Synthesis of (Di)thiahelicenes and Dithiophenohelicenes by [2+2+2] Cycloisomerization of Alkynes

A series of inherently chiral (di)thiahelicenes/dithiophenohelicenes containing 5, 6, 9 or 11 (hetero)cycles in their helical backbone with thiophene subunit(s) embedded in it or annulated to its periphery were uniformly synthesized by intramolecular alkyne [2+2+2] cycloisomerization. Their structural, chemical and physicochemical properties such as crystal packing, oxidation, barrier to racemization, spontaneous thin film transformation or electrochemical behavior were studied and compared with the respective properties of the parent all-carbon helicenes and dibenzohelicenes.

Automated summary

A series of inherently chiral di- and tetrathiahelicenes/dithiophenohelicenes were synthesized and their structural and physicochemical properties were studied and compared with other related compounds.