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

Photoisomerizable azobenzene-containing oxacalixarenes

GARGIULLI, Claudia;GATTUSO, Giuseppe;NOTTI, Anna;PARISI, Melchiorre;PUNTORIERO, Fausto
2012

Abstract

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
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11570/1917613
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