Syntheses and properties of functionalized oxacalix[4]arene porphyrins

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. H-1 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. (C) 2007 Elsevier Ltd. All rights reserved.