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Contorted Arene‐fused Metallophthalocyanines
Author(s) -
Suzuki Hiroyuki,
Kobayashi Nagao,
Kimura Mutsumi
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500532
Subject(s) - chemistry , planarity testing , palladium , phenanthrenes , aromaticity , electrophile , pyrene , phenanthrene , phthalocyanine , zinc , molecular orbital , photochemistry , polymer chemistry , computational chemistry , catalysis , organic chemistry , crystallography , molecule
Three phthalonitriles 9 – 11 fused with planar and nonplanar polycyclic aromatic hydrocarbons were synthesized through a combination of palladium‐catalyzed coupling, electrophilic cyclization, and Scholl oxidation reactions. The equilibrium geometries and electronic structures of the frontier orbitals of 9 – 11 were simulated by computation calculations. The optimized structure of 11 is found to have a larger torsional angle than that of 10 because of the non‐planarity arising from some cove and fjord regions. Zinc complexes 1 – 3 fused with polycyclic aromatic hydrocarbons were synthesized by the cyclotetramerization of 9 – 11 . The attachment of nonplanar polycyclic aromatic hydrocarbons with phthalocyanine rings prevented the formation of aggregates in the solid state.