2,2,4,6-Tetraaryl-2H-benzo[h]chromenes: The influence of electronic communication between aryl substituents on their photochromism

Stuart Aiken, Georgina K. Armitage, Orlando D.C.C. de Azevedo, Daniel L. Crossley, Rhianne Dobson, Christopher D. Gabbutt, B. Mark Heron, Denis Jacquemin, Craig R. Rice, Nicola Soltowska

Research output: Contribution to journalArticlepeer-review

Abstract

A series of photochromic 2,2,4,6-tetraaryl-2H-benzo[h]chromenes have been efficiently synthesised by two complementary strategies employing the condensation of 1,1,3-triarylprop-2-yn-1-ols with 4-substituted 1-naphthols and Suzuki cross-coupling chemistry. The novel 1,1,3-triarylpropynols were readily obtained either by the addition of an arylacetylide to the requisite benzophenones or by a Sonogashira coupling of a halobenzene with a preformed 1,1-diarylprop-2-yn-1-ol. The tetraarylbenzochromenes which possessed a strong electron withdrawing aryl moiety at C-4 exhibited good room temperature photochromism. The combination of a strong electron donating aryl group at C-6 with a strong electron withdrawing aryl group at C-4 resulted in the generation of a photomerocyanine which exhibited two absorption bands in the visible region of the electromagnetic spectrum, rather than one broad band when the C-6 aryl group was only weakly electron donating. Remarkably inverting the electronic nature of the C-4 and C-6 aryl groups resulted in the inhibition of photochromism and instead led to fluorescence. TD-DFT calculations were used to rationalise the shift from photochromism to fluorescence.

Original languageEnglish
Article number110036
Number of pages24
JournalDyes and Pigments
Volume199
Early online date23 Dec 2021
DOIs
Publication statusE-pub ahead of print - 23 Dec 2021

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