Optical Activity and Helicity Enhancement of Highly Sensitive Dinaphthylmethane-Based Stereodynamic Probes for Secondary Alcohols.

ABSTRACT: Chirality transfer from circular dichroism (CD)-silent secondary alcohol (inductor) to the stereodynamic bichromophoric di(1-naphthyl)methane probe (reporter) led to the generation of intense, induced exciton-type Cotton effects (CEs) in the ultraviolet-visible absorption region. The di(1-naphthyl)methane probe exhibits extraordinarily high sensitivity to even small structural variations of the alcohol skeleton, that is, the probe is able to distinguish between an oxygen atom and a methylene group in a 3-hydroxytetrahydrofurane skeleton. Signs and amplitudes of the exciton couplets of ¹B_b electronic transition might be correlated with the type of stereo-differentiating parts of the molecule flanking the stereogenic center, however, not with the absolute configuration.

SUBMITTER: Madry T 

PROVIDER: S-EPMC6648851 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature