Chiroptical properties and racemization behavior of highly distorted donor-acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality

Hideaki Saito, Tadashi Mori, Yumi Origane, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Absolute configuration of optically active 7,12-bis(dicyanomethylene)-7,12- dihydrobenz[a]anthracene (1) with interconvertible planar chirality was determined by a comparison of experimental and theoretical circular dichroism (CD) spectra. Upon standing at ambient temperatures, 1 was found to spontaneously racemize, the rates of which were assessed through the separation profiles of chiral HPLC at 5-20°C and also from the CD spectral decay profiles at the same temperatures. Mechanism of the racemization was discussed.

Original languageEnglish
Pages (from-to)278-281
Number of pages4
JournalChirality
Volume20
Issue number3-4
DOIs
Publication statusPublished - 2008 Mar 3
Externally publishedYes

Keywords

  • Absolute configuration
  • Charge-transfer interaction
  • Circular dichroism
  • Planar chirality
  • Racemization
  • TD-DFT calculation
  • Tetracyanoquinodimethane

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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