Electronic interactions between π-stacked chromophores in nonsymmetric tertiary naphthyl Di- And polyarylureas

Grace B.Delos Santos, Frederick D Lewis*

*Corresponding author for this work

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The synthesis, structure, and spectroscopy of a family of tertiary di- and polyarylureas possessing a naphthyl and several different arene end groups separated by a variable number of internal phenylenediamine linking groups are reported. Molecular modeling and 1H NMR chemical shift data are consistent with the formation of compact, folded structures in which the arene groups adopt a splayed face-to-face geometry. The structure and solvent dependence of the electronic absorption and emission spectra have been determined and are interpreted with the aid of ZINDO calculations. The electronic absorption spectra are relatively insensitive to the choice of arene end group, the number of linking groups, and the solvent polarity. In contrast, the solution fluorescence is highly dependent upon the structure and solvent polarity. These observations are attributed to a small change in polarity upon excitation of the ground state to a naphthalene-localized Franck-Condon singlet state, which can undergo relaxation to a highly polar emissive state with extensive charge-transfer character.

Original languageEnglish (US)
Pages (from-to)8106-8112
Number of pages7
JournalJournal of Physical Chemistry A
Volume109
Issue number36
DOIs
StatePublished - Sep 15 2005

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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