Facile synthesis of 9,10,19,20-tetraarylporphycenes

Ganapathi, Emandi ; Chatterjee, Tamal ; Ravikanth, Mangalampalli (2014) Facile synthesis of 9,10,19,20-tetraarylporphycenes European Journal of Organic Chemistry, 2014 (30). pp. 6701-6706. ISSN 1434-193X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...

Related URL: http://dx.doi.org/10.1002/ejoc.201402770


A simple route was developed for the synthesis of 9,10,19,20-tetraarylporphycenes by combining both McMurry and oxidative synthetic strategies and using readily available precursors. The desired 5,6-diaryldipyrroethenes, which were prepared in multigram quantities over two steps, were used to prepare 9,10,19,20-tetraarylporphycenes under mild acid-catalyzed conditions. As 5,6-diaryldipyrroethene precursors can easily be prepared in multigram quantities, this method is useful for the preparation of meso-tetrarylporphycenes that contain different aryl substituents. The molecular structures of these macrocycles were determined by HRMS analysis as well as 1D and 2D NMR studies. The tetraarylporphycenes exhibited a strong Soret band at approximately 380 nm and three Q bands in the region of 580–655 nm. The tetraarylprophycenes are reasonably fluorescent and stable under redox conditions.

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