Substituent-induced circular dichroism in phthalocyanines

Nagao Kobayashi, Ryuji Higashi, Bruno C. Titeca, Folker Lamote, Arnout Ceulemans

Research output: Contribution to journalArticlepeer-review

78 Citations (Scopus)

Abstract

Phthalocyanines with two and four optically active binaphthyl units have been synthesized and characterized by electronic absorption, CD, and MCD spectroscopy. The chiral substituents induce CD in the in-plane polarized Q and Soret bands of phthalocyanines: phthalocyanines having R and S binaphthyls show positive and negative CD, respectively. The geometries of the compounds were optimized at the PM3 level, and a vector coupling model for the induction of rotatory strength was developed. This model provides a semi-quantitative description of the CD spectra. Thus, not only the sign of the CD spectra but also the intensity relationship between the Soret and Q CD bands and, further, the shape of the Q CD band were reasonably explained. The discussion focuses on the important role of the central hydrogen atoms.

Original languageEnglish
Pages (from-to)12018-12028
Number of pages11
JournalJournal of the American Chemical Society
Volume121
Issue number51
DOIs
Publication statusPublished - 1999 Dec 29

ASJC Scopus subject areas

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

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