Journal
TETRAHEDRON LETTERS
Volume 53, Issue 6, Pages 616-619Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.11.114
Keywords
Oxacalixarenes; Metacyclophanes; Azobenzene; Photoisomerization; Photoresponsive heteracalixarenes
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Funding
- MIUR [PRIN-2009A5Y3N9]
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The first examples of photo-responsive azobenzene-containing oxacalixarenes have been synthesized via a 3+1 macrocyclization approach. Introduction of the photoresponsive unit was achieved by using 4-phenylazoresorcinol or (E)-4-(4'-nitrophenylazo)resorcinol as the nucleophilic component in the macrocyclization reaction. These novel macrocycles have been characterized by means of ID and 2D NMR spectroscopy and DFT calculations (B3LYP/6-31G(d)). According to thermal and photoisomerization studies, tetranitro-oxacalix[4]arenes are less prone to E -> Z isomerization than oxacalix[2]arene[2]triazines and, within the two series, p-nitrophenylazo derivatives are more unwilling to isomerize than their phenylazo analogues. (C) 2011 Elsevier Ltd. All rights reserved.
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