Absolute configuration of chiral [2.2]Paracyclophanes with intramolecular charge-transfer interaction. Failure of the exciton chirality method and use of the sector rule applied to the cotton effect of the CT transition

Takahiro Furo, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

53 Citations (Scopus)

Abstract

Optically active 4,7-dicyano-12,15-dimethoxy[2.2]paracyclophanes have been separated by chiral HPLC and their absolute configurations determined by comparison of the experimental and the theoretical VCD spectra. X-ray crystallographic structures for both diastereomers are also reported. The electronic circular dichroism spectra of these enantiomeric pairs, as chiral intramolecular charge-transfer complexes, have been obtained for the first time. The exciton coupling method, usually used for determining the absolute configuration of chiral molecules, however, did not give a correct prediction for the present CT-paracyclophane system. Instead, empirical sector rules for the signs of the Cotton effects of the CT transition can be applied for the assignment of the absolute configuration.

Original languageEnglish
Pages (from-to)8242-8243
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number23
DOIs
Publication statusPublished - 2005 Jun 15
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Absolute configuration of chiral [2.2]Paracyclophanes with intramolecular charge-transfer interaction. Failure of the exciton chirality method and use of the sector rule applied to the cotton effect of the CT transition'. Together they form a unique fingerprint.

Cite this