New mixed-substituent amino/carboxyphenylporphyrins for a dye-sensitized TiO₂ solar cell were prepared using several synthetic routes. The reaction of 4-carbomethoxy- and 4-acetamidobenzaldehydes with pyrrole in propionic acid under aerobic conditions afforded mixtures of mixed amide/ester substituted tetraphenylporphyrins which were separated using centrifugal chromatography then deprotected to give the target compounds. Condensation of p-nitrophenyldipyrromethane with 4-carbomethoxybenzaldehyde in CH₂Cl₂ catalyzed by trifluoroacetic acid, followed by oxidation with dichlorodicyanoquinone gives trans-dicarbomethoxy/dinitrophenylporphyrin, which when treated with SnCl₂ and HCl affords the trans-diamino/dicarboxy derivative, trans-TA₂C₂PP. Commercially available tetrakis-5,10,15,20-(4-carboxyphenyl)porphyrin (TCPP) was converted to mixtures of mixed amino/carbomethoxyphenylporphyrins using hydroxylamine hydrochloride in polyphosphoric acid with methanol workup. Relative yields and product distributions from each route are discussed and the optoelectronic characteristics of the synthesized porphyrins were studied using UV-visible spectroscopy and cyclic voltammetry.

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Vol. 11, No. 08

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Received 10 May 2007

Accepted 18 July 2007

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Syntheses and optoelectronic properties of amino/carboxyphenylporphyrins for potential use in dye-sensitized TiO2 solar cells

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Syntheses and optoelectronic properties of amino/carboxyphenylporphyrins for potential use in dye-sensitized TiO₂ solar cells