Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 52, Pages 14592-14595Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408398
Keywords
BODIPY; chiral resolution; circular dichroism; density functional calculations; exciton chirality method
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Funding
- DFG
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The exciton chirality method (ECM) is commonly recognized as one of the best approaches to assign the absolute configuration of biaryls. This paper reports the first exception to this method for a simple biaryl system. ECD and VCD measurements in combination with DFT (B3LYP/6-311G*), TDDFT (CAM-B3LYP/6-311G*), and Coupled-Cluster (RISCS-CC2) calculations were used to determine the absolute configurations of axially chiral BODIPY DYEmers. The ECM fails to predict the sign of the intense CD couplet at 500 nm of the 1,1'-coupled dimer. The odd behavior was rationalized by considering the strong transition magnetic dipole associated with the 500 nm transition, which leads to an unexpected dominance of the mm coupling at the expense of the mm one in these compounds. This is the first case in which a strong mm coupling hampers the use of the ECM, but this behavior should not be restricted to the BODIPY chromophore.
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