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Tetrachelate Porphyrin Chromophores for Metal Oxide Semiconductor Sensitization:  Effect of the Spacer Length and Anchoring Group Position

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Contribution from the Chemistry Department, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, and Center of Molecular Devices, Department of Chemistry, Royal Institute of Technology, Teknikringen 30, SE 100 44 Stockholm, Sweden
Cite this: J. Am. Chem. Soc. 2007, 129, 15, 4655–4665
Publication Date (Web):March 27, 2007
https://doi.org/10.1021/ja068218u
Copyright © 2007 American Chemical Society

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    Abstract

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    Four Zn(II)-tetra(carboxyphenyl)porphyrins in solution and bound to metal oxide (TiO2, ZnO, and ZrO2) nanoparticle films were studied to determine the effect of the spacer length and anchoring group position (para or meta) on their binding geometry and photoelectrochemical and photophysical properties. The properties of three types of anchoring groups (COOH and COONHEt3) for four Zn(II)-porphyrins (Zn(II)-5,10,15,20-tetra(4-carboxyphenyl)porphyrin (p-ZnTCPP), Zn(II)-5,10,15,20-tetra(3-carboxyphenyl)porphyrin (m-ZnTCPP), Zn(II)-5,10,15,20-tetra(3-(4-carboxyphenyl)phenyl)porphyrin (m-ZnTCP2P), and Zn(II)-5,10,15,20-tetra(3-ethynyl(4-carboxyphenyl)phenyl)porphyrin (m-ZnTC(PEP)P)) were compared. In m-ZnTCPP, m-ZnTCP2P, and m-ZnTC(PEP)P the four anchoring groups are in the meta position on the meso-phenyl rings of the porphyrin macrocycle, thus favoring a planar binding mode to the metal oxide surfaces. The three meta-substituted porphyrin salts have rigid spacer units of increasing length (phenyl (P), biphenyl (P2), and diphenylethynyl (PEP)) between the porphyrin ring and the carboxy anchoring groups, thus raising the macrocycle from the metal oxide surface. All porphyrins studied here, when bound to TiO2 and ZnO, exhibited quenching of the fluorescence emission, consistent with electron injection into the conduction band of the semiconductor. Steady-state UV−vis and fluorescence studies of p-ZnTCPP on insulating ZrO2 showed evidence of aggregation and exciton coupling. This was not observed in any of the meta-substituted porphyrins. The photoelectrochemical properties (IPCE, Voc, and Isc) of the porphyrins bound to TiO2 films in solar cells have been measured and rationalized with respect to the sensitizer binding geometry and distance from the surface.

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     Rutgers University.

     Royal Institute of Technology.

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    Preparation of the TiO2 and ZrO2 films; TiO2 Raman, PXRD, and AFM data; p-H2TCPP-[E], m-H2TCPP-[E], p-ZnTCPP-[E], m-ZnTCPP-[E], p-ZnTCPP-[A], and m-ZnTCPP-[A] NMR data; FT-IR-ATR spectra of 1d and e, 2d and e, 3d and e neat and bound to TiO2. This material is available free of charge via the Internet at http://pubs.acs.org.

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