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

• Published in: Helvetica chimica acta Vol. 105; no. 3
• Main Authors: Palata, Ondřej, Andronova, Angelina, Šámal, Michal, Nejedlý, Jindřich, Rybáček, Jiří, Buděšínský, Miloš, Bednárová, Lucie, Pospíšil, Lubomír, Císařová, Ivana, Starý, Ivo, Stará, Irena G.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.03.2022; Wiley Subscription Services, Inc
• Subjects: alkyne cycloisomerization; Alkynes; Chemistry; Chemistry, Multidisciplinary; chirality; Crystal structure; Electrochemical analysis; Electrochemistry; helical structures; Isomerization; Oxidation; Physical Sciences; Physicochemical properties; Racemization; redox properties; Science & Technology; thiahelicenes; Thin films; thiophene derivatives; ROUTE; ASYMMETRIC-SYNTHESIS; chirality; ENANTIOSELECTIVE SYNTHESIS; helical structures; alkyne cycloisomerization; CRYSTAL-STRUCTURES; STEREOSELECTIVE SYNTHESES; thiahelicenes; PHOTOPHYSICAL PROPERTIES; ONE HUNDRED YEARS; MOLECULES; thiophene derivatives; HELICAL CHIRALITY; SULFUR-COMPOUNDS; redox properties
• ISSN: 0018-019X; 1522-2675
• DOI: 10.1002/hlca.202100225

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.