TY - JOUR
T1 - Cyclophanes Containing Bowl-Shaped Aromatic Chromophores
T2 - Three Isomers of anti-[2.2](1,4)Subphthalocyaninophane
AU - Liu, Quan
AU - Shimizu, Soji
AU - Kobayashi, Nagao
N1 - Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA.
Copyright:
Copyright 2015 Elsevier B.V., All rights reserved.
PY - 2015/4/20
Y1 - 2015/4/20
N2 - 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 1H 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.
AB - 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 1H 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.
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U2 - 10.1002/anie.201411510
DO - 10.1002/anie.201411510
M3 - Article
AN - SCOPUS:84927731945
VL - 54
SP - 5187
EP - 5191
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 17
ER -