An alternative synthesis of β-pyrrolic acetylene-substituted porphyrins

被引：16

作者：

Stephenson, Adam W. I. ^{[1
]}

Wagner, Pawel ^{[2
,3
]}

Partridge, Ashton C. ^{[1
]}

Jolley, Kenneth W. ^{[1
]}

Filichev, Vyacheslav V. ^{[1
]}

Officer, David L. ^{[2
,3
]}

机构：

[1] Massey Univ, IFS MacDiarmid Ctr, Palmerston North, New Zealand

[2] Univ Wollongong, Intelligent Polymer Res Inst, Wollongong, NSW 2522, Australia

[3] Univ Wollongong, Dept Chem, ARC Ctr Excellence Electromat Sci, Wollongong, NSW 2522, Australia

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 39期

关键词：

D O I：

10.1016/j.tetlet.2008.07.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modified Horner-Emmons condensation reaction has been employed in the synthesis of acetylene-substituted porphyrins at the beta-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'-carboxyphenyl)ethynyl-5,10,15,20-tetraphenylporphyrinato zinc(II) showed a red shift compared to the double bond equivalent, 4-(trans-2'-(2 ''-(5 '', 10 '', 15 '',20 ''-tetraphenylporphyrinato zinc(II)yl))ethen-1'-yl)-1-benzoic acid. Comparison of the X-ray structures of 2-((4'-formyl)phenyl)ethynyl-5,10,15,20-tetraphenylporphyrinato zinc(II) and its analogue 4-(trans-2'(2 ''-(5 '',10 '',15 '',20 ''-tetraphenylporphyrinato copper(II)yl))ethen-1'-yl)-1-benzaldehyde showed all unexpected decrease in planarity in the analogue with the triple bond as opposed to that with the double bond. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5632 / 5635

页数：4

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