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

0556447 - ÚOCHB 2023 RIV CH eng J - Journal Article
Palata, O. - Andronova, Angelina - Šámal, Michal - Nejedlý, Jindřich - Rybáček, Jiří - Buděšínský, Miloš - Bednárová, Lucie - Pospíšil, Lubomír - Císařová, I. - Starý, Ivo - Stará, Irena G.
Synthesis of (Di)thiahelicenes and Dithiophenohelicenes by [2+2+2] Cycloisomerization of Alkynes.
Helvetica Chimica Acta. Roč. 105, č. 3 (2022), č. článku e202100225. ISSN 0018-019X. E-ISSN 1522-2675
R&D Projects: GA ČR(CZ) GA20-23566S
Institutional support: RVO:61388963
Keywords : alkyne cycloisomerization * chirality * helical structures * redox properties * thiahelicenes * thiophene derivatives
OECD category: Organic chemistry
Impact factor: 1.8, year: 2022
Method of publishing: Limited access
https://doi.org/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.
Permanent Link: http://hdl.handle.net/11104/0330664