Abstract
A novel, optically-active N 21–N 22, N 23–N 24 bis-carbonyl-bridged bilirubin congener 1 with propionic acids replaced by sec-butyls exhibits a strong negative exciton chirality circular dichroism spectrum from the ( S, S)-enantiomer. Molecular dynamics calculations favor the M -helical diastereomer by 0.4 kJ/mol over the P . The dipyrrinone model 2 of one half of 1 exhibits an almost undetectable circular dichroism. Unlike 1, which is only very weakly fluorescent, 2 is strongly fluorescent, with quantum yield ϕ F ∼ 0.70.
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