Exciton Chirality. (A) Origins of and (B) Applications from Strongly Fluorescent Dipyrrinone Chromophores |
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Authors: | Stefan E Boiadjiev and David A Lightner |
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Institution: | (1) Department of Chemistry, University of Nevada, Reno, NV 89557-0020, USA; |
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Abstract: | (A) The origin of exciton interaction and examples of its application to organic stereochemistry are presented. (B) N,N-Carbonyl-bridged dipyrrinones constitute a new class of highly fluorescent chromophores suitable for investigations of stereochemistry and absolute configuration. N,N-Carbonylxanthobilirubic acid esters are strongly fluorescent, with a fluorescence quantum yield (F) 0.8, but produce only weak exciton CD from the trans-1,2-cyclohexanediol template. The ester of an analog with benzoic acid replacing propionic, N,N-carbonyl-8-(4-carboxyphenyl)-3-ethyl-2,7,9-trimethyl-(10H)-dipyrrin-1-one, exhibits strong fluorescence (F=0.68, em=493nm, ex=422nm in CHCl3) and UV-Vis absorption (21000 at 424nm) in organic solvents. Its diester with (1S,2S)-cyclohexanediol is fluorescent and exhibits exciton circular dichroism (=+15dm3·mol–1·cm–1, =432nm; =–4dm3·mol–1cm–1, =380nm) that correlates with the Exciton Chirality Rule. |
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