Syntheses and properties of functionalized oxacalix[4]arene porphyrins

Lijuan Jiao, Louisiana State University
Erhong Hao, Louisiana State University
Frank R. Fronczek, Louisiana State University
Kevin M. Smith, Louisiana State University
M. Graça H. Vicente, Louisiana State University

Abstract

Six new functionalized oxacalix[4]arene porphyrins have been synthesized via a high-yielding '3+1' condensation between meso-(3,5-dihydroxyphenyl)triphenylporphyrin and readily available new fluorodinitrobenzene-containing trimers. The X-ray structure of one linear trimer is presented. The synthesis of a porphyrin containing two oxacalix[4]arene moieties is also reported using a similar strategy. 1H NMR data and computer calculations using the AM1 semiempirical method incorporated into the Spartan program indicate that the oxacalix[4]arene porphyrins adopt 1,3-alternating conformations. The photophysical properties of the oxacalix[4]arene porphyrins were investigated. © 2007 Elsevier Ltd. All rights reserved.