☆ 4.4 Article

Convergent synthesis of meso-ferrocenyl porphyrins for TiO2 sensitization

TETRAHEDRON LETTERS (2012)

Journal

TETRAHEDRON LETTERS

Volume 53, Issue 35, Pages 4700-4703

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tetlet.2012.06.093

Keywords

Porphyrin; Ferrocene; Dipyrromethane; TiO2

Categories

Chemistry, Organic

Funding

University of Massachusetts Boston

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Abstract

Electron-donating ferrocenyl moieties have been incorporated into supramolecular carboxyporphyrin architectures Zn(II)-5-ferrocenyl-10,20-bistolyl-15-(4-methylbenzoate)porphyrin (trans-Fc-ZnP-CO2Me), Zn(II)-5-ferrocenyl-10,15,20-tris(4-methylbenzoate)porphyrin [trans-Fc-ZnP-(CO2Me)(3)], and Zn(II)-5,15-bisferrocenyl-10,20-bis(4-benzoate)porphyrin Itrans-Fc(2)-ZnP-(CO2Me)(2)] for self-assembly on metal oxide nanoparticles. Efficient and economic synthesis has required a convergent strategy toward reduced symmetry trans-A(2)B(2) and trans-AB(2)C substitution patterns about the porphyrin macrocycle minimizing the production of porphyrin side products and increasing yields of the target ferrocenylporphyrins. Preliminary spectroscopic data in solution and in the solid state bound to mesoporous TiO2 films are discussed. (c) 2012 Elsevier Ltd. All rights reserved.

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