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An alternative synthesis of β-pyrrolic acetylene-substituted porphyrins

✍ Scribed by Adam W.I. Stephenson; Pawel Wagner; Ashton C. Partridge; Kenneth W. Jolley; Vyacheslav V. Filichev; David L. Officer

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
218 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

A modified Horner-Emmons condensation reaction has been employed in the synthesis of acetylenesubstituted porphyrins at the b-pyrrolic position. This technique was shown to have many advantages over the typically employed Sonogashira coupling method, including negating the requirement for a brominated porphyrin starting material. The electronic spectra of 2-(4 0 -carboxyphenyl)ethynyl-5,10,15,20tetraphenylporphyrinato zinc(II) showed a red shift compared to the double bond equivalent, 4-(trans-2 0 -(2 00 -(5 00 ,10 00 ,15 00 ,20 00 -tetraphenylporphyrinato zinc(II)yl))ethen-1 0 -yl)-1-benzoic acid. Comparison of the X-ray structures of 2-((4 0 -formyl)phenyl)ethynyl-5,10,15,20-tetraphenylporphyrinato zinc(II) and its analogue 4-(trans-2 0 -(2 00 -(5 00 ,10 00 ,15 00 ,20 00 -tetraphenylporphyrinato copper(II)yl))ethen-1 0 -yl)-1-benzaldehyde showed an unexpected decrease in planarity in the analogue with the triple bond as opposed to that with the double bond.

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