Bistricyclic aromatic enes annelated with nopinane fragment

Bistricyclic aromatic enes annelated with nopinane fragment Full article

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 2021, Volume: 83, Article number : 131979, Pages count : DOI: 10.1016/j.tet.2021.131979

Tags

Overcrowded alkenes; Nopinane-annelated pyridines; 4,5-Diazafluorene; Mechanochromism; pH sensing

Authors

Vasilyev Eugene S. ¹ , Bizyaev Sergey N. ¹ , Komarov Vladislav Yu ² , Tkachev Alexey ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Academician Lavrentiev Ave, Novosibirsk 9, Russia
2	(Данные Web of science) Russian Acad Sci, Nikolaev Inst Inorgan Chem, Siberian Branch, Novosibirsk 630090, Russia

Organic compounds, referred to as bistricyclic aromatic enes (BAE), are a subgroup among many sterically overcrowded alkenes and are widely studied as molecular switches. We have developed a new group of chiral BAE whose molecular structure combines dipinodiazafluorene fragment and chromophore/fluorophore (acridine, xanthene or thioxanthene moiety). The new compounds demonstrate mechanochromism, thermochromism, and solvatochromism/protonochromism. According to quantum chemical calculations (DFT PBE0/def2-TZVPP), the compounds synthesized are conformationally inhomogeneous, and the conformations should differ in the electronic absorption spectra, the population of conformational isomers should being dependent on the solvent and the acidity of the medium. The observed experimental facts (NMR data, UV spectra, chromism, X-ray data) are in good correlation with the calculated data. (C) 2021 Elsevier Ltd. All rights reserved.

Vasilyev E.S. , Bizyaev S.N. , Komarov V.Y. , Tkachev A.
Bistricyclic aromatic enes annelated with nopinane fragment
Tetrahedron. 2021. V.83. 131979 . DOI: 10.1016/j.tet.2021.131979 WOS Scopus РИНЦ

Published print:

Mar 1, 2021

Web of science	WOS:000629261100016
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