Conformer-specific photoisomerizaton of some 2-vinylbiphenyls

Frederick D Lewis*, Xiaobing Zuo

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

The ground-state conformations, spectroscopy, and photochemistry of 2-vinylbiphenyl and three of its vinyl-substituted derivatives have been investigated. The ground state exists as a mixture of syn and anti conformers in which the vinyl group is directed either toward or away from the unsubstituted phenyl ring. Both conformers are highly non-planar, having large phenyl-phenyl and phenyl-vinyl dihedral angles. The vinylbiphenyls are found to undergo conformer-specific photochemistry. The syn rotamers are non-fluorescent and undergo rapid and efficient cyclization to 8a,9-dihydrophenanthrene intermediates, which undergo rapid thermal sigmatropic rearrangements to yield 9,10-dihydrophenanthrenes. The intermediates have been generated at 77 K and detected by absorption spectroscopy. The singlet states of the anti rotamers are fluorescent, and undergo competing intersystem crossing and activated C=C torsion. The torsional barriers are of the order of those for styrenes with similar vinyl substituents.

Original languageEnglish (US)
Pages (from-to)1059-1066
Number of pages8
JournalPhotochemical and Photobiological Sciences
Volume2
Issue number11
DOIs
StatePublished - Nov 1 2003

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Cell Biology
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biophysics

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