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 language | English |
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Pages (from-to) | 12018-12028 |
Number of pages | 11 |
Journal | Journal of the American Chemical Society |
Volume | 121 |
Issue number | 51 |
DOIs | |
Publication status | Published - 1999 Dec 29 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry