Dibenzoindolo[1,8]naphthyridines: Synthesis and Characterization of X-Shaped Aza[4,6]helicenes.

Autor: Ausekle E; Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059, Rostock, Deutschland., Ehlers P; Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059, Rostock, Deutschland.; Leibniz Institut für Katalyse, Albert Einstein Str. 29a, 18059, Rostock, Deutschland., Villinger A; Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059, Rostock, Deutschland., Langer P; Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059, Rostock, Deutschland.; Leibniz Institut für Katalyse, Albert Einstein Str. 29a, 18059, Rostock, Deutschland.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jan 16; Vol. 30 (4), pp. e202303225. Date of Electronic Publication: 2023 Nov 27.
DOI: 10.1002/chem.202303225
Abstrakt: This report describes a one-pot multi-step procedure to obtain double azahelicenes via nucleophilic fluorine substitution of 2,2-di(2-bromophenyl)-1,1-difluoroalkenes and palladium-catalysed ring closing reaction. The developed synthesis approach allows easy diversification of substituents at all four fragments of the obtained X-shaped aza[4,6]helicene entity. Yields range from 20 % to 60 % among 12 product examples. X-ray single crystal analysis reveals formation of (P,P) and (M,M) enantiomer mixture of products. Optical and electrochemical properties of selected products were studied by performing UV/Vis absorption, photoluminescence and cyclic voltammetry measurements. Experimental results are supported by (TD)-DFT, NICS and NICS2BC calculations.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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