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Chemistry. 2014 Sep 8;20(37):11708-18. doi: 10.1002/chem.201403667. Epub 2014 Aug 21.

Synthesis and photophysical properties of multichromophoric carbonyl-bridged triarylamines.

Author information

1
Macromolecular Chemistry I, Bayreuther Institut für Makromolekülforschung (BIMF) and Bayreuther Zentrum für Kolloide und Grenzflächen (BZKG), University of Bayreuth, 95440 Bayreuth (Germany), Fax: (+49) 921-55-3206.

Abstract

The synthesis and photophysical properties of two novel multichromophoric compounds is presented. Their molecular design comprises a carbonyl-bridged triarylamine core and either naphthalimides or 4-(5-hexyl-2,2'-bithiophene)naphthalimides as second chromophore in the periphery. The lateral chromophores are attached to the core via an amide linkage and a short alkyl spacer. The synthetic approach demonstrates a straightforward functionalization strategy for carbonyl-bridged triarylamines. Steady-state and time-resolved spectroscopic investigations of these compounds, in combination with three reference compounds, provide clear evidence for energy transfer in both multichromophoric compounds. The direction of the energy transfer depends on the lateral chromophore used. Furthermore, the compound bearing the lateral 4-(bithiophene)naphthaimides is capable of forming fluorescent gels at very low concentrations in the sub-millimolar regime whilst retaining its energy transfer properties.

KEYWORDS:

bridged triarylamines; donor-acceptor molecules; energy transfer; fluorescent gels; multichromophoric compounds

PMID:
25147099
DOI:
10.1002/chem.201403667

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