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Cyclophanes Containing Bowl‐Shaped Aromatic Chromophores: Three Isomers of anti ‐[2.2](1,4)Subphthalocyaninophane
Author(s) -
Liu Quan,
Shimizu Soji,
Kobayashi Nagao
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201411510
Subject(s) - chromophore , chemistry , crystallography , conjugated system , circular dichroism , regular polygon , boron , spectroscopy , magnetic circular dichroism , linear dichroism , materials science , polymer , physics , photochemistry , geometry , organic chemistry , mathematics , spectral line , quantum mechanics , astronomy
The connection of bowl‐shaped aromatic boron subphthalocyanines with anti ‐[2.2]paracyclophane resulted in the first observation of electronic communication between convex and concave surfaces. Three isomers of anti ‐[2.2](1,4)subphthalocyaninophane, described as concave–concave ( CC ), convex–concave ( CV ), and convex–convex ( VV ) according to the orientation of the subphthalocyanine units, were synthesized and characterized by various spectroscopic techniques, including 1 H NMR, electronic absorption, fluorescence, and magnetic circular dichroism spectroscopy and X‐ray crystallography, together with molecular‐orbital calculations. On going from the CC system to CV and further to VV , the Q band broadened and finally split as a result of through‐space expansion of the conjugated systems, which were also reproduced theoretically.