Synthesis and stereochemistry of chiral aza-boraspirobifluorenes with tetrahedral boron-stereogenic centers.

Dalton Trans

Department of Chemistry, Faculty of Science, Tokyo University of Science, Shinjuku, Tokyo 162-8601, Japan.

Published: November 2022

AI Article Synopsis

  • Chiral aza-boraspirobifluorenes were synthesized and their structural and photophysical properties were analyzed.
  • Enantiomers were separated using chiral HPLC, and their absolute stereochemistry was confirmed through comparison of experimental and theoretical circular dichroism spectra.
  • A kinetic analysis showed that the racemization process is primarily determined by the cleavage of the B-N bond.

Article Abstract

We have synthesized chiral aza-boraspirobifluorenes and evaluated their structural and photophysical properties. Enantiomers were separated by chiral HPLC on a semi-preparative scale, and the absolute stereochemistry was determined by comparison of experimental circular dichroism (CD) spectra and theoretical electronic CD (ECD) spectra. A kinetic analysis combined with theoretical calculations revealed that the rate-determining step of the racemization involves the cleavage of the B-N bond.

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http://dx.doi.org/10.1039/d2dt03303hDOI Listing

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Article Synopsis
  • Chiral aza-boraspirobifluorenes were synthesized and their structural and photophysical properties were analyzed.
  • Enantiomers were separated using chiral HPLC, and their absolute stereochemistry was confirmed through comparison of experimental and theoretical circular dichroism spectra.
  • A kinetic analysis showed that the racemization process is primarily determined by the cleavage of the B-N bond.
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