Intermolecular and supramolecular photoinduced electron transfer processes of fullerene–porphyrin/phthalocyanine systems

Abstract The attainment of a better understanding of the dependence of photoinduced electron transfer reaction rates on the molecular structures of the donor and acceptor entities results in improving the capture and storage of solar energy. Here, the intermolecular and supramolecular electron transfer processes from electron donors (porphyrins (P), chlorophylls (Chl), phthalocyanines (Pc) and naphthalocyanines (Nc)) and their metal derivatives to electron acceptors (fullerenes such as C 60 and C 70 ) studied by nanosecond and picosecond laser flash photolysis techniques in polar and nonpolar solvents are reviewed. For intermolecular systems in polar solvents, photoinduced electron transfer takes place via the excited triplet states of C 60 /C 70 or via the excited triplet states of P/Pc/Nc, yielding solvated radical ions in polar solvents; thus, the back electron transfer rates are generally slow. In the case of the supramolecular dyads and triads formed by axial coordination, hydrogen bonding, crown ether complexation, or rotaxane formation, the photoinduced charge separation takes place mainly from the excited singlet state of the donor; however, the back electron transfer rates are generally quite fast. The relations between structures and photochemical reactivities of these novel supramolecular systems are discussed in relation to the efficiency of charge separation and charge recombination.

[1]  M. Zandler,et al.  Structural studies of a non-covalently linked porphyrin–fullerene dyad , 2001 .

[2]  Kevin M. Smith,et al.  Porphyrins and metalloporphyrins. , 1975 .

[3]  J. S. Connolly,et al.  Photochemical Conversion and Storage of Solar Energy , 1981 .

[4]  N. Turro,et al.  Photosensitization by reversible electron transfer: theories, experimental evidence, and examples , 1986 .

[5]  M. Prato,et al.  Reversible zinc phthalocyanine fullerene ensembles. , 2002, Chemical communications.

[6]  K. Hwang,et al.  Vectorial electron transfer from an interfacial photoexcited porphyrin to ground-state fullerene C60 and C70 and from ascorbate to triplet C60 and C70 in a lipid bilayer , 1992 .

[7]  H. Willigen,et al.  Energy- and Electron-Transfer Quenching of Porphyrin Triplets by C601 , 2000 .

[8]  Thomas A. Moore,et al.  Molecular mimicry of photosynthetic energy and electron transfer , 1993 .

[9]  A. Watanabe,et al.  Electron Transfer from Tetrathiafulvalenes to Photoexcited C70 Studied by Observing Transient Absorption in the Near-IR Region , 1997 .

[10]  François Diederich,et al.  Supramolecular fullerene chemistry , 1999 .

[11]  Kock Yee. Law,et al.  Organic photoconductive materials: recent trends and developments , 1993 .

[12]  A. Watanabe,et al.  Solvent Polarity Effect on Photoinduced Electron Transfer between C60 and Tetramethylbenzidine Studied by Laser Flash Photolysis , 1995 .

[13]  K. Hwang,et al.  Photoinduced electron transport across a lipid bilayer mediated by C70 , 1993, Nature.

[14]  Heinz D. Roth.  A brief history of photoinduced electron transfer and related reactions , 1990 .

[15]  Neal R Armstrong,et al.  Phthalocyanines and porphyrins as materials , 2000 .

[16]  Dapeng Xu,et al.  Spectral behavior of cis-2′,5′-dipyridinylpyrrolidino[3′,4′:1,2][60]fullerene and its coordination complex with Zinc porphyrin (ZnTPP) , 2002 .

[17]  R. Ion,et al.  Photocurrent generation in an electrochemical cell with substituted metalloporphyrins , 2000 .

[18]  J. Deisenhofer,et al.  The Photosynthetic Reaction Center , 1993 .

[19]  J. Fujisawa,et al.  Pulsed and cw-time-resolved EPR studies of photoinduced electron transfer between zinc(II) porphyrin and fullerene , 1998 .

[20]  B. Röder,et al.  Photoinduced intramolecular electron transfer in covalently linked porphyrin–triptycene–(bis)quinone diads and triads , 1999 .

[21]  M. El-Khouly,et al.  Efficient photoinduced electron transfer between C60/C70 and zinc octaethylporphyrin studied by nanosecond laser photolysis method , 2000 .

[22]  A. Watanabe,et al.  Substituent and solvent effects on photoexcited states of functionalized fullerene[60] , 1998 .

[23]  J. W. Owens,et al.  Photophysical properties of porphyrins, phthalocyanines, and benzochlorins , 1998 .

[24]  Kosmas Prassides,et al.  Physics and chemistry of the fullerenes , 1994 .

[25]  Y. Matano,et al.  Nanostructured artificial photosynthesis , 2003 .

[26]  J. Bolton,et al.  Reversible photooxidation of chlorophyll. Study of the chlorophyll-benzoquinone system utilizing flash photolysis and electron spin resonance spectroscopy , 1972 .

[27]  G. Marconi,et al.  Synthesis and electronic properties of donor-linked fullerenes towards photochemical molecular devices , 2000 .

[28]  K. Yoshihara,et al.  Primary processes in plant photosynthesis : photosystem I reaction center , 2000 .

[29]  M. Prato,et al.  Efficient charge separation in porphyrin-fullerene-ligand complexes. , 2001, Chemistry.

[30]  Y. Amao,et al.  Photoinduced hydrogen production with the system containing water-soluble viologen-linked porphyrins and hydrogenase , 2002 .

[31]  J. Silber,et al.  Synthesis and photophysical properties of Zn(II) porphyrin–C60 dyad with potential use in solar cells , 2002 .

[32]  G. Kavarnos,et al.  Fundamentals of Photoinduced Electron Transfer , 1993 .

[33]  N. Gupta,et al.  C60 as a Photocatalyst of Electron-Transfer Processes: Reactions of Triplet C60 with Chloranil, Perylene, and Tritolylamine Studied by Flash Photolysis and FT-EPR , 1996 .

[34]  M. Prato,et al.  Photoinduced electron transfer in multicomponent arraysof a π-stacked fullerene porphyrin dyad and diazabicyclooctane or afulleropyrrolidine ligand , 2000 .

[35]  S. Fukuzumi,et al.  Uphill Photooxidation of NADH Analogues by Hexyl Viologen Catalyzed by Zinc Porphyrin-Linked Fullerenes† , 2002 .

[36]  Francis D'Souza,et al.  Spectroscopic, Electrochemical, and Photochemical Studies of Self-Assembled via Axial Coordination Zinc Porphyrin−Fulleropyrrolidine Dyads† , 2002 .

[37]  S. Itoh,et al.  Modification of photosystem I reaction center by the extraction and exchange of chlorophylls and quinones. , 2001, Biochimica et biophysica acta.

[38]  A. Hirsch.  Chemistry of Fullerenes , 1994 .

[39]  Jong‐In Hong,et al.  Colorimetric anion sensing by porphyrin-based anion receptors , 2001 .

[40]  V. Balzani.  Electron transfer in chemistry , 2001 .

[41]  C. Wamser,et al.  Solvent and substituent effects on the redox properties of free-base tetraphenylporphyrins in DMSO and aqueous DMSO , 1992 .

[42]  Francis D'Souza,et al.  Electronic Interactions and Photoinduced Electron Transfer in Covalently Linked Porphyrin−C60(pyridine) Diads and Supramolecular Triads Formed by Self-Assembling the Diads and Zinc Porphyrin , 2002 .

[43]  M. Prato,et al.  Parallel (face-to-face) versus perpendicular (edge-to-face) alignment of electron donors and acceptors in fullerene porphyrin dyads: the importance of orientation in electron transfer. , 2001, Journal of the American Chemical Society.

[44]  Stephen R. Wilson,et al.  Synthesis and photophysics of a linear non-covalently linked porphyrin-fullerene dyad. , 2003, Chemical communications.

[45]  K. Ohkubo,et al.  Small Reorganization Energy of Intramolecular Electron Transfer in Fullerene-Based Dyads with Short Linkage , 2002 .

[46]  M. El-Khouly,et al.  Photoinduced electron transfer between metal octaethylporphyrins and fullerenes (C60/C70) studied by laser flash photolysis: electron-mediating and hole-shifting cycles , 2002 .

[47]  M. El-Khouly,et al.  Photoinduced electron transfer from triplet states of phthalocyanines to fullerenes studied by transient absorption spectroscopies in visible and near‐IR regions , 2000 .

[48]  C. Brabec,et al.  Long-lived photoinduced charge separation for solar cell applications in phthalocyanine–fulleropyrrolidine dyad thin films , 2003 .

[49]  J. Nierengarten,et al.  A supramolecular cup-and-ball C60-porphyrin conjugate system. , 2003, Chemical communications.

[50]  Fred Wudl,et al.  Two different fullerenes have the same cyclic voltammetry , 1991 .

[51]  K. Kadish,et al.  Electroreduction of buckminsterfullerene, C60, in aprotic solvents : electron spin resonance characterization of singly, doubly, and triply reduced C60 in frozen solutions , 1992 .

[52]  Ya‐Ping Sun,et al.  Intramolecular electron transfer in fullerene derivatives with multiple donors , 2002 .

[53]  O. Ito,et al.  Photoinduced intrarotaxane electron transfer between zinc porphyrin and [60]fullerene in benzonitrile. , 2003, Angewandte Chemie.

[54]  Steven L. Murov,et al.  Handbook of photochemistry , 1973 .

[55]  Akihiko Tsuda,et al.  Fully Conjugated Porphyrin Tapes with Electronic Absorption Bands That Reach into Infrared , 2001, Science.

[56]  W. Eberhardt,et al.  Phthalocyanine/C60 composites as improved photosensitive materials , 1999 .

[57]  C. Wamser,et al.  Substituent and solvent effects on the hyperporphyrin spectra of diprotonated tetraphenylporphyrins , 2003 .

[58]  P. Piotrowiak.  Photoinduced electron transfer in molecular systems: Recent developments , 1999 .

[59]  O. Ito,et al.  PHOTOINDUCED ELECTRON TRANSFER BETWEEN C60/C70 AND ZINC TETRAPHENYLPORPHYRIN IN POLAR SOLVENTS , 1998 .

[60]  K. Asai,et al.  Novel optical oxygen sensing material: platinum porphyrin-fluoropolymer film , 2000 .

[61]  R. Murray,et al.  Electrochemistry of various substituted aminophenyl iron porphyrins: Part I. Redox properties of dissolved, adsorbed and electropolymerized species , 1989 .

[62]  A. Blank,et al.  Triplet porphyrins as donors in intramolecular electron transfer and their intermolecular interaction with free radicals , 2001 .

[63]  D. Rehm,et al.  Kinetics of Fluorescence Quenching by Electron and H‐Atom Transfer , 1970 .

[64]  Maksudul M. Alam,et al.  Photoinduced Electron Transfer from Phthalocyanines to Fullerenes (C60 and C70) , 1997 .

[65]  N. Kobayashi.  Dimers, trimers and oligomers of phthalocyanines and related compounds , 2002 .

[66]  Yoshiteru Sakata,et al.  Donor‐Linked Fullerenes: Photoinduced electron transfer and its potential application , 1997 .

[67]  Shu-Hua Cheng,et al.  Substituent and axial ligand effects on the electrochemistry of zinc porphyrins , 2002 .

[68]  K. Kalyanasundaram.  Photochemistry of Polypyridine and Porphyrin Complexes , 1992 .

[69]  A. Watanabe,et al.  Photoinduced Electron Transfer Between Chlorophylls (a/b) and Fullerenes (C60/C70) Studied by Laser Flash Photolysis¶ , 2001, Photochemistry and photobiology.

[70]  F. D’Souza,et al.  Probing the donor-acceptor proximity on the physicochemical properties of porphyrin-fullerene dyads: "tail-on" and "tail-off" binding approach. , 2001, Journal of the American Chemical Society.

[71]  S. Mattes,et al.  Exciplexes and Electron Transfer Reactions , 1984, Science.

[72]  M. Michel-beyerle,et al.  Ultrafast charge separation and driving force dependence in cyclophane-bridged Zn-porphyrin-quinone molecules , 1996 .

[73]  F. Diederich,et al.  A new pyridyl-substituted methanofullerene derivative. Photophysics, electrochemistry and self-assembly with zinc(II) meso-tetraphenylporphyrin (ZnTPP) , 1999 .

[74]  B. Tromberg,et al.  SINGLET OXYGEN GENERATION OF PORPHYRINS, CHLORINS, AND PHTHALOCYANINES , 1989, Photochemistry and photobiology.

[75]  S. Fukuzumi,et al.  Catalytic effects of dioxygen on intramolecular electron transfer in radical ion pairs of zinc porphyrin-linked fullerenes. , 2001, Journal of the American Chemical Society.

[76]  A. Watanabe,et al.  Efficient photoinduced electron transfer between C60 and tetrathiafulvalenes studied by nanosecond laser photolysis , 1997 .

[77]  M. Goldberg,et al.  Charge oscillation in the homolysis of MeX derivatives , 1992 .

[78]  B. Bowler,et al.  Porphyrin to quinone electron transfer across a depsipeptide which forms an α-helical turn , 2000 .

[79]  A. Hirsch,et al.  Self-organisation in photoactive fullerene porphyrin based donor–acceptor ensembles , 2001 .

[80]  M. Zandler,et al.  Photoinduced Electron Transfer in “Two-Point” Bound Supramolecular Triads Composed of N,N-Dimethylaminophenyl-Fullerene-Pyridine Coordinated to Zinc Porphyrin , 2003 .

[81]  F. Diederich,et al.  Covalent Fullerene Chemistry , 1996, Science.

[82]  Michael R. Wasielewski,et al.  Photoinduced electron transfer in supramolecular systems for artificial photosynthesis , 1992 .

[83]  S. Nath,et al.  Effect of solvent polarity on the aggregation of fullerenes: a comparison between C60 and C70 , 2002 .

[84]  J. Fujisawa,et al.  Direct observation of electron spin polarization transfer in triplet–triplet energy transfer between porphyrins and fullerene in fluid solution , 1998 .

[85]  Dirk M Guldi,et al.  Fullerene-porphyrin architectures; photosynthetic antenna and reaction center models. , 2002, Chemical Society reviews.

[86]  Luis Echegoyen,et al.  Electrochemical detection of C606- and C706-: Enhanced stability of fullerides in solution , 1992 .

[87]  B. Albinsson,et al.  Bridge-dependent electron transfer in porphyrin-based donor-bridge-acceptor systems. , 2001, Journal of the American Chemical Society.

[88]  D. Guldi,et al.  Electron-Transfer Reactions between C60 and Radical Ions of Metalloporphyrins and Arenes , 1994 .

[89]  Y. Shirota.  Organic materials for electronic and optoelectronic devices , 2000 .

[90]  D. Whitten,et al.  Spectroscopic studies of formation and decay of triplet exciplexes. Evidence for a limited role of charge-transfer interactions in a nonpolar solvent , 1974 .

[91]  F. D’Souza,et al.  Self-assembled supramolecular triad composed of fulleropyrrolidine bearing two pyridine moieties axially coordinated to two zinc porphyrins , 2003 .

[92]  O. Ito,et al.  Photoinduced electron transfer of the triplet states of C60 and C70 from oxotitanium(IV) tetra-t-butyl-phthalocyanine as an electron-donor in polar solvent , 2003 .

[93]  Jayan Thomas,et al.  Optical absorption and emission spectral studies of phthalocyanine molecules in DMF , 2001 .

[94]  A. Watanabe,et al.  Photoinduced Electron Transfer between C60 and Polysilane Studied by Laser Flash Photolysis in the Near-IR Region , 1994 .

[95]  A. Lever,et al.  Phthalocyanines : properties and applications , 1989 .

[96]  F. D’Souza,et al.  Self-Assembled Porphyrin-C(60) and Porphycene-C(60) Complexes via Metal Axial Coordination. , 1999, Inorganic chemistry.

[97]  M. Prato,et al.  A noncovalently linked, dynamic fullerene porphyrin dyad. Efficient formation of long-lived charge separated states through complex dissociation , 1999 .

[98]  M. Hayvalı,et al.  Titrations in non-aqueous media: potentiometric investigation of symmetrical and unsymmetrical tetra-aryl porphyrins with 4-nitrophenyl and 4-aminophenyl substituents in nitrobenzene solvent. , 1999, Talanta.