862897-17-4Relevant academic research and scientific papers
A simple route to prepare monofunctionalised 21-thia-, 21,23-dithia-, and 21-thia-23-oxaporphyrins from unsymmetrical thiophene diols and their use in the synthesis of covatently linked unsymmetrical porphyrin dimers
Punidha, Sokkalingam,Agarwal, Neeraj,Ravikanth, Mangalampalli
, p. 2500 - 2517 (2007/10/03)
A series of unsymmetrical thiophene diols has been prepared in two steps from thiophene in 16-46 % yields. The unsymmetrical thiophene diols containing functionalised aryl groups were then used as key synthons for the synthesis of a series of monofunctionalised 21-thia (N3S), 21,23-dithia (N 2S2) and 21-thia-23-oxaporphyrins (N2SO). Condensation of one equivalent of unsymmetrical diol with either two equivalents of aldehyde and three equivalents of pyrrole, one equivalent of symmetrical 16-thiatripyrrane or one equivalent of symmetrical 16-oxatripyrrane under standard porphyrin-forming conditions resulted in monofunctionalised 21-thia-, 21,23-dithia- or 21-thia-23-oxaporphyrins in decent yields. This unsymmetrical diol method is simple, versatile and gives an access for the first time to any desired mono-functionalised porphyrins with N3S, N2S2 and N2SO porphyrin cores. The use of monofunctionalised N3S, N3S2 and N 2SO porphyrins is further demonstrated by synthesising the first examples of three new covalently linked diarylethyne-bridged unsymmetrical dimers containing two different porphyrin cores such as N2S 2-N4, N2S2-N3S and N 2S2-N2SO. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
