Acta Chimica Sinica 2012, 70(17) 1791-1797 DOI: 10.3724/SP.J.1005.2008.00225    ISSN: 0567-7351 CN: 31-1320/O6

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Chiral Phthalocyanine with Unambiguous Absolute Molecular Structures for Both Enantiomers
Wang Kanga, Wang Hailonga, Mack Johnb, Li Wenjuna, Kobayashi Nagaob, Jiang Jianzhuanga
a Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry, University of Science and Technology Beijing, Beijing 100083, China;
b Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
Abstract:  (R)- and (S)-Enantiomers of chiral metal free tetrakis(dinaphtho[1,2-e:1',2'-g]-1,4-dioxocine)-[2,3-b;2',3'-k;2'',3''-t; 2''',3'''-c']phthalocyanine (1) were synthesized via a cyclic tetramerization of the corresponding optically active benzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dioxocine-5,6-dicarbonitrile (2) in refluxing n-pentanol in the presence of lithium followed by treatment with acetic acid. This novel chiral phthalocyanine compound has been characterized by a series of spectroscopic methods in addition to elemental analysis. The absolute molecular structures of both enantiomers have been unambiguously elucidated by single crystal X-ray diffraction analysis, resulting in the direct assignment of the chirality of metal free phthalocyanine 1.
Keywords: phthalocyanine   chiral   optically active   absolute molecular structure   single crystal X-ray diffraction analysis  
Received  2012-05-31   Revised    Online  2012-07-18  
DOI: 10.6023/A12050262
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