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Short Paper | Regular issue | Vol 98, No. 10, 2019, pp.1445-1454
Published online, 8th November, 2019
DOI: 10.3987/COM-19-14160
A Propeller-Shaped Mesomeric Betaine, Tetraphenylbenzene-1-Quinolinium-2-Benzoate

Sviatoslav Batsyts, Felix Lederle, Eike G. Hübner, Jörg Adams, Jan C. Namyslo, and Andreas Schmidt*

*Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany

Abstract

4-[(Quinolin-4-yl)ethynyl]benzoic acid underwent a cycloreaction with tetraphenylcyclopentadienone to give the hexa(hetero)arylbenzene- 1-(quinolin-4-yl)-2-(4-benzoic acid)-3,4,5,6-tetraphenylbenzene which was N-methylated and finally deprotonated to give the title compound. The molecule adopts a propeller-shaped configuration in which the benzoate ring as well as the phenyl ring adjacent to the quinolinium substituent display non-isochronous resonance frequencies, respectively, due to a hindered rotation. Although the molecule formally belongs to the class of pseudo-cross-conjugated heterocyclic mesomeric betaines, the propeller-shape causes a charge distribution of cross-conjugated systems. DFT-calculations (frontier orbital profiles, geometries) have been carried out.