Synthesis and photophysical properties of fluorescent 2-aryl-1,3-dialkylbenzimidazolium ions and a l-alkyl-2-arylbenzimidazole with excited state intramolecular proton-transfer |
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Authors: | Joel M. Kauffman Ali Khalaj Peter T. Litak John A. Novinski Gurdip S. Bajwa |
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Abstract: | To improve the solubility, photostability and fluorescence quantum yield (Φ) of 2-arylbenzimidazolium ions the N-1 hydrogen was replaced by an alkyl group before N-3 was quatemized; this substitution did not reduce Φ, proving the absence of steric inhibition to attainment of coplanarity in the excited state. A related symmetrical 2,2′-arylenebis(1,3-dimethyldibenzimidazolium ion) had Φ = 0.86. The related 2,5-bis(1-methyl-2-benzimidazolyl)phenol had Φ = 0.38 at 22° as well as a very large Stokes' shift due to proton-transfer. These findings supported a new insight into the electron distribution of the first excited singlet state of oligophenylenes. The compounds are of interest as laser dyes and scintillation fluors. |
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