Synthesis and structure-property relationships of donor/acceptor-functionalized bis(dehydrobenzo[18]annuleno)benzenes

Organic & Biomolecular Chemistry
Eric L Spitler, Michael M Haley

Abstract

Seven new bis(dehydrobenzo[18]annuleno)benzenes (bis[18]DBAs) functionalized with electron-donating dibutylamino groups and/or accepting nitro groups at various positions along the peripheries of the chromophores have been prepared. The effects of varying the donor/acceptor charge transfer pathways, chromophore lengths and molecular symmetries upon the optical band gaps are studied using UV-visible spectroscopy, and structure-property correlations are identified. It is found that bis[18]DBAs possessing donor-pi-donor and acceptor-pi-acceptor pathways exhibit the smallest band gaps, especially when an acceptor-pi-acceptor pathway is situated along the longest chromophore length in the molecule. The all-donor species is also found to exhibit efficient fluorescence with dramatic solvatochromism. The results may have value to the rational design of future NLO/TPA device components.

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Citations

Sep 30, 2014·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Boris ZimmermannDubravka Gembarovski
Feb 11, 2014·The Journal of Organic Chemistry·Andrew L KorichThomas S Hughes
Dec 31, 2008·Journal of the American Chemical Society·Roslyn S ButlerRonald K Castellano
Sep 27, 2014·The Journal of Organic Chemistry·Sharwatie RamsaywackRik R Tykwinski
Dec 3, 2011·The Journal of Organic Chemistry·Paul N W BaxterAlexandre Varnek
Mar 11, 2010·Advanced Materials·François Diederich, Milan Kivala
May 30, 2008·The Journal of Organic Chemistry·Matthew J O'ConnorMichael M Haley
Nov 13, 2010·The Journal of Organic Chemistry·Thanh LuuRik R Tykwinski

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