132313-34-9Relevant academic research and scientific papers
Rational Tetraarylporphyrin Syntheses: Tetraarylporphyrins from the MacDonald Route
Wallace, David M.,Leung, Sam H.,Senge, Mathias O.,Smith, Kevin M.
, p. 7245 - 7257 (2007/10/02)
Four new synthetic routes to meso-tetraarylporphyrins using a MacDonald-type 2 + 2 condensation are described.Self-condensation of a 5-arylpyrromethane (e.g., 17) with an aryl-substituted one-carbon bridging unit affords a mixture of tetraarylporphyrins due to acid-catalyzed redistribution reactions.The second and third methods presented here show wide applicability for the preparation of 5,10,15,20-tetraaryl-substituted porphyrins (e.g., 31, 37, 48, 49) with 2-fold rotational symmetry and involve self-condensation of 5-aryl-1-aryldipyrromethanecarbinols.Finally, the fourth approach involves a 2 + 2 approach in which one of the two dipyrromethanes bears both of the bridging carbons in the porphyrin products, affording porphyrin 50 which possesses three different aryl rings, with one pair of uniquely opposite identical aryl groups.The last two 2 + 2 methods are further extended to give a tetraarylporphyrin 38 bearing four different aryl groups in a predesignated array, the structure of which is confirmed by a single-crystal X-ray study.
STEPWISE SYNTHESES OF UNSYMMETRICAL TETRA-ARYLPORPHYRINS. ADAPTATION OF THE MACDONALD DIPYRROLE SELF-CONDENSATION METHODOLOGY
Wallace, David M.,Smith, Kevin M.
, p. 7265 - 7268 (2007/10/02)
A new synthetic route to meso-tetraarylporphyrins using a MacDonald-type 2+2 condensation is established.The method presented here shows wide applicability for the preparation of 5,10,15,20-tetra-arylsubstituted porphyrins with two-fold rotational symmetry.The 2+2 method is further extented to give a tetraarylporphyrin (14) bearing four different aryl groups in a predesignated array.
