Issue 8, 2016

Control of the intermolecular photodimerization of anthracene derivatives by hydrogen bonding of urea groups in dilute solution

Abstract

The photodimerization reaction of anthracene derivatives was performed by capitalizing on intermolecular hydrogen bonds. Anthracene derivatives that can control the dimerization reaction depending on the substitution site were designed by using two anthryl moieties and one urea group, referred to as N,N′-dianthracen-n-ylurea, nDAU (n = 1, 2 and 9), which are symmetrically substituted by 1-anthryl, 2-anthryl and 9-anthryl groups, respectively. We investigated the excimer emission and photodimerization reaction of these anthracene–urea derivatives using absorption, emission, and 1H NMR spectroscopy along with fluorescence decay measurements. All derivatives showed a concentration dependence of their fluorescence spectra and multiple fluorescence lifetime components even at 10−6 M. Significantly, 9DAU resulted in an intermolecular photodimerization reaction. These differences in photoreactivity of nDAU may depend on variations in the overlap of the intermolecularly associated anthracene rings of nDAU by hydrogen bonding between intermolecular urea moieties. Furthermore, the dimerization quantum yield of 9DAU was reduced by the addition of tetrabutylammonium acetate (TBAAc). Consequently, we revealed that the substitution site and the addition of TBAAc affected the dimerization reaction of anthracene–urea derivatives.

Graphical abstract: Control of the intermolecular photodimerization of anthracene derivatives by hydrogen bonding of urea groups in dilute solution

Supplementary files

Article information

Article type
Paper
Submitted
27 Apr 2016
Accepted
12 Jul 2016
First published
13 Jul 2016

Photochem. Photobiol. Sci., 2016,15, 1071-1079

Control of the intermolecular photodimerization of anthracene derivatives by hydrogen bonding of urea groups in dilute solution

H. Matsumoto, Y. Nishimura and T. Arai, Photochem. Photobiol. Sci., 2016, 15, 1071 DOI: 10.1039/C6PP00125D

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