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Article

Fluorescence of Half-Twisted 10-Acyl-1-methyltetrahydrobenzoquinolines

by
Christopher Abelt
*,
Ian Day
,
Junkai Zhao
and
Robert Pike
Department of Chemistry, College of William and Mary, Williamsburg, VA 23185, USA
*
Author to whom correspondence should be addressed.
Submission received: 17 May 2024 / Revised: 18 June 2024 / Accepted: 20 June 2024 / Published: 25 June 2024
(This article belongs to the Special Issue Feature Papers in Photochemistry and Photocatalysis)

Abstract

The steric interference of proximal dialkyl amino and acyl groups at the peri (1,8) positions of naphthalene affects the intramolecular charge transfer fluorescence. Previous studies indicate that acyl and freely rotating dimethyl amino groups twist toward coplanarity with the naphthalene ring in the excited state. The present study examines the effect of constraining the amino group in a ring. The photophysical properties of 2,2-dimethyl-1-(1-methyl-1,2,3,4-tetrahydrobenzo[h]quinolin-10-yl)propan-1-one (4), ethyl 1-methyl-1,2,3,4-tetrahydrobenzo[h]quinoline-10-carboxylate (5), and 1-methyl-1,2,3,4-tetrahydrobenzo[h]quinoline-10-carbaldehyde (6) are compared with the dimethyl amino derivatives 2 and 3. Crystal structures of 46 show that the amine ring adopts a chair conformation, where the N-methyl group is axial. Computational results suggest that the pyramidal amino group planarizes and twists together with the acyl toward coplanarity in the excited state. The ring structure does not thwart the formation of a planar intramolecular charge transfer (PICT) state.
Keywords: solvato-chromism; charge transfer; PICT; TICT; peri solvato-chromism; charge transfer; PICT; TICT; peri

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MDPI and ACS Style

Abelt, C.; Day, I.; Zhao, J.; Pike, R. Fluorescence of Half-Twisted 10-Acyl-1-methyltetrahydrobenzoquinolines. Molecules 2024, 29, 3016. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29133016

AMA Style

Abelt C, Day I, Zhao J, Pike R. Fluorescence of Half-Twisted 10-Acyl-1-methyltetrahydrobenzoquinolines. Molecules. 2024; 29(13):3016. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29133016

Chicago/Turabian Style

Abelt, Christopher, Ian Day, Junkai Zhao, and Robert Pike. 2024. "Fluorescence of Half-Twisted 10-Acyl-1-methyltetrahydrobenzoquinolines" Molecules 29, no. 13: 3016. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29133016

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