Azine-fused [6]carbohelicenes: synthesis, crystal structure, stereoisomerism and optical properties

Azine-fused [6]carbohelicenes: synthesis, crystal structure, stereoisomerism and optical properties Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2026, Volume: 24, Number: 23, Pages: 4842-4851 Pages count : 10 DOI: 10.1039/d6ob00620e

Authors

Marchenko Sergey S. ¹ , Sokha Samita J. ¹ , Demidov Oleg P. ² , Chernyshev Anatoly V. ³ , Metelitsa Anatoly V. ³ , Brig Sergei S. ^4,5 , Prolomov Ilya V. ⁵ , Medvedev Michael G. ⁵ , Gulevskaya Anna V. ¹

Affiliations

1	Department of Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation
2	Department of Chemistry and Pharmacy, North Caucasus Federal University, Pushkin str. 1a, 355017 Stavropol, Russian Federation
3	Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka ave., Rostov-on-Don 344090, Russian Federation
4	Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russian Federation
5	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prosp., 47, Moscow, Russian Federation

Novel azine-fused [6]helicenes were prepared in five synthetic steps starting from commercially available 2,3-dihaloazines (2,3-dibromopyridine, 2,3-dichloropyrazine and 2,3-dichloroquinoxaline). The X-ray structures, UV-vis absorption and fluorescence spectra of the helicenes were investigated and compared to those of the parent [6]carbohelicene. It was shown that pyrazine-fused [6]helicenes, bearing a pyren-1-yl or 1,8-bis(dimethylamino)naphthalen-4-yl side substituent, contain both helical and axial stereogenic elements and exist as a mixture of stable (P,Sa)-, (M,Ra)-, (P,Ra)- and (M,Sa)-isomers at room temperature. The barriers to R/S- and P/M-isomerizations, as well as the relative stabilities of the isomers, were estimated theoretically.

Marchenko S.S. , Sokha S.J. , Demidov O.P. , Chernyshev A.V. , Metelitsa A.V. , Brig S.S. , Prolomov I.V. , Medvedev M.G. , Gulevskaya A.V.
Azine-fused [6]carbohelicenes: synthesis, crystal structure, stereoisomerism and optical properties
Organic & Biomolecular Chemistry. 2026. V.24. N23. P.4842-4851. DOI: 10.1039/d6ob00620e WOS Scopus OpenAlex

Submitted:	Apr 16, 2026
Published online:	Jun 17, 2026

≡ Web of science:	WOS:001780410900001
≡ Scopus:	2-s2.0-105040560572
≡ OpenAlex:	W7161848711