Chiral Phthalocyanine with Unambiguous Absolute Molecular Structures for Both Enantiomers

(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]lphthalocyanine (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 relluxing n-pentanol in the presence of lithium followed by treatment with acetic acid. This novel chiral phthalocyaninc 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 I.