Abstract
We have constructed a variety of molecular assemblies of porphyrin as a donor and fullerene as an acceptor on electrodes for molecular photoelectrochemical devices. Highly efficient energy- and electron-transfer processes have been realized at gold electrodes modified with self-assembled monolayers of porphyrin- or fullerene linked systems mimicking light-harvesting and charge separation in bacterial photosynthesis. Highly ordered organization of porphyrins and fullerenes has also been achieved using step-by-step self-assembly of porphyrin and fullerene units by association with gold nanoparticles or dendrimers on tin oxide electrodes, which exhibit high power-conversion efficiency of up to 1.5%. These results will provide valuable information on the design of donor–acceptor type molecular assemblies that can be tailored to construct highly efficient organic solar cells.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Abbreviations
- CR:
-
charge recombination
- CS:
-
charge separation
- Fc:
-
ferrocene
- FF:
-
fill factor
- IPCE:
-
incident photon-to-photocurrent efficiency
- ITO:
-
indium tin oxide
- MV2+ :
-
methyl viologen
- P:
-
porphyrin
- SAM:
-
self-assembled monolayer
- SnO2 :
-
tin oxide
References
CJ Brabec, NS Sariciftci and JC Hummelen, Plastic solar cells. Adv Funct Mater 11 (2001) 15
DM Guldi and KD Asumus, Electron transfer from C76 (C 2νȁ9) and C78 (D 2) to radical cations of various arenes: evidence for the Marcus inverted region. J Am Chem Soc 119 (1997) 5744
DM Guldi and M Prato, Electrostatic interactions by design.Versatile methodology towards multifunctional assemblies/nanostructured electrodes. Chem Comm 2004 (2004) 2517
T Hasobe, H Imahori, S Fukuzumi and PV Kamat, Quaternary self-organization of porphyrin and fullerene units by clusterization with gold nanoparticles on SnO2 electrodes for organic solar cells. J Am Chem Soc 125 (2003) 1496
T Hasobe, H Imahori, PV Kamat, TK Ahn, SK Kim, D Kim, A Fujimoto, T Hirakawa and S Fukuzumi, Photovoltaic cells using composite nanoclusters of porphyrins and fullerenes with gold nanoparticles. J Am Chem Soc 127 (2005) 1216
T Hasobe, PV Kamat, MA Absalom, Y Kashiwagi, J Sly, MJ Crossley, K Hosomizu, H Imahori and S Fukuzumi, Supramolecular photovoltaic cells based on composite molecular nanoclusters: dendritic porphyrin and C60, porphyrin dimer and C60, and porphyrin-C60 dyad. J Phys Chem B 108 (2004) 1286
H Imahori, M Arimura, T Hanada, Y Nishimura, I Yamazaki, Y Sakata and S Fukuzumi, Photoactive three-dimensinal monolayers: porphyrin alkanethiolate-stabilized gold clusters. J Am Chem Soc 123 (2001c) 335
H Imahori, S Cardoso, D Tatman, S Lin, L Noss, GR Seely, L Sereno, JC Silber, TA Moore, AL Moore and D Gust, Photoinduced electron transfer in a carotenobuckminsterfullerene dyad. Photochem Photobiol 62 (1995a) 1009
H Imahori, K Hagiwara, T Akiyama, M Aoki, S Taniguchi, T Okada, M Shirakawa and Y Sakata, The small reorganization energy of C60 in electron transfer. Chem Phys Lett 263 (1996) 545
H Imahori, K Hagiwara, T Akiyama, S Taniguchi, T Okada and Y Sakata, Synthesis and photophysical property of porphyrin-linked fullerene. Chem Lett 1995 (1995b) 256
H Imahori, H Norieda, Y Nishimura, I Yamazaki, K Higuchi, N Kato, T Motohiro, H Yamada, K Tamaki, M Arimura and Y Sakata, Chain length effect on the structure and photoelectrochemical properties of self-assembled monolayers of porphyrins on gold electrodes. J Phys Chem B 104 (2000b) 1253
H Imahori, H Norieda, H Yamada, Y Nishimura, I Yamazaki, Y Sakata and S Fukuzumi, Light-harvesting and photocurrent generation by gold electrodes modified with mixed self-assembled monolayers of boron dipyrrin and ferrocene-porphyrin-fullerene triad. J Am Chem Soc 123 (2001b) 100
H Imahori, K Tamaki, DM Guldi, C Luo, M Fujitsuka, O Ito, Y Sakata and S Fukuzumi, Modulating charge separation and charge recombination dynamics in porphyrin-fullerene linked dyad and triads; Marcus-normal versus inverted region. J Am Chem Soc 123 (2001a) 2607
H Imahori, H Yamada, Y Nishimura, I Yamazaki and Y Sakata, Vectorial multistep electron transfer at the gold electrodes modified with self-assembled monolayers of ferrocene-porphyrin-fullerene triads. J Phys Chem B 104 (2000a) 2099
H Imahori, H Yamada, S Ozawa, K Ushida and Y Sakata, Synthesis and photoelectrochemical properties of a self-assembled monolayer of a ferrocene-porphyrin-fullerene triad on a gold electrode. Chem Commun 1999 (1999) 1165
PV Kamat, S Barazzouk, S Hotchandani and KG Thomas, Nanostructured thin films of C60−aniline dyad clusters: electrodeposition, charge separation, and photoelectrochemistry. Chem Eur J 6 (2000) 3914
G McDermott, SM Prince, AA Freer, AM Hawthornthwaite-Lawless, MZ Papiz, RJ Cogdell and NW Isaacs, Crystal structure of an integral membrane light-harvesting complex from photosynthetic bacteria. Nature 374 (1995) 517
AM Oijen, M Ketelaars, J Köhler, TJ Aartsma and J Schmidt, Unraveling the electronic structure of individual photosynthetic pigment-protein complexes. Science 285 (1999) 400
DA Tomalia, AM Naylor and WAIII Goddard, Starburst dendrimers: control of size, shape, surface chemistry, topology and flexibility in the conversion of atoms to macroscopic materials. Angew Chem Int Ed Engl 29 (1990) 138
A Ulman, Formation and structure of self-assembled monolayers. Chem Rev 96 (1996) 1533
EKL Yeow, KP Ghiggino, J NH Reek, MJ Crossley, AW Bosman, APHJ Schenning and EW Meijer, The dynamics of electronic energy transfer in novel multiporphyrin functionalized dendrimers: a time-resolved fluorescence anisotropy study. J Phys Chem B 104 (2000) 2596
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Umeyama, T., Imahori, H. Self-Organization of Porphyrins and Fullerenes for Molecular Photoelectrochemical Devices. Photosynth Res 87, 63–71 (2006). https://doi.org/10.1007/s11120-005-4632-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11120-005-4632-z