Large face to face tetraphenylporphyrin/fullerene nanoaggregates. A DFT study

Organic Electronics

Volumn 14, Issue 10, 2013, Pages 2617-2627

  Castillo, Ulises Jiménez ^a   Guadarrama, Patricia ^a   Fomine, Serguei ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

DFT; Dispersion correction; Fullerene; Porphyrin; Reorganization energy

Indexed keywords

CHARGE TRANSFER; DISPERSIONS; ELECTRON TRANSPORT PROPERTIES; ENERGY GAP; FULLERENES; IONIZATION POTENTIAL; POLARONS; PORPHYRINS; ZINC;

DISPERSION CONTRIBUTION; DISPERSION CORRECTION; DISPERSION INTERACTION; ELECTRON TRANSPORT; ELECTRONIC EXCITATION; LOW-ENERGY EXCITATIONS; REORGANIZATION ENERGIES; TETRAPHENYL PORPHYRINS;

BINDING ENERGY;

EID: 84885481662     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2013.05.032     Document Type: Article

References (27)

1. C.J. Brabec (Ed.), Organic Photovoltaics: Concepts and Realization, Springer, Berlin, 2003.
2. C.J. Brabec, V. Dyakonov, U. Scherf (Eds.), Organic Photovoltaics: Materials, Device Physics, and Manufacturing Technologies, Wiley VCH, Weinheim, 2008.
3. N.R. Armstrong, W.N. Wang, D.M. Alloway, D. Placencia, E. Ratcliff, M. Brumbach, Organic/organic heterojunctions: organic light emitting diodes and organic photovoltaic devices, Macromol. Rapid Commun. 30 (2009) 717-731.
4. A. de la Escosura, M.V. Martinez-Diaz, T. Torres, R.H. Grubbs, D.M. Guldi, H. Neugebauer, C. Winder, M. Drees, N.S. Sariciftci, New donor-acceptor materials based on random polynorbornenes bearing pendant phthalocyanine and fullerene units, Asian J. Chem. 1 (2006) 148-154. (Pubitemid 44389174)
5. G. Bottari, G. de la Torre, D.M. Guldi, T. Torres, Covalent and noncovalent phthalocyanine-carbon nanostructure systems: synthesis, photoinduced electron transfer, and application to molecular photovoltaics, Chem. Rev. 110 (2010) 6768-6816.
6. S. Gunes, H. Neugebauer, N.S. Sariciftci, Conjugated polymer-based organic solar cells, Chem. Rev. 107 (2007) 1324-1338. (Pubitemid 46736541)
7. P.D.W. Boyd, M.C. Hodgson, L. Chaker, C.E.F. Rickard, A.G. Oliver, P.J. Brothers, R. Bolskar, F.S. Tham, C.A. Reed, Selective supramolecular fullerene porphyrin interactions, J. Am. Chem. Soc. 121 (1999) 10487-10495. (Pubitemid 129551069)
8. J.L. Segura, N. Martin, Fullerene dimers, Chem. Soc. Rev. 29 (2000) 13-25.
9. M.D. Meijer, G.P.M. van Klink, G. van Koten, Metal-chelating capacities attached to fullerenes, Coord. Chem. Rev. 230 (2002) 141-163.
10. D.M. Guldi, Fullerene-porphyrin architectures; photosynthetic antenna and reaction center models, Chem. Soc. Rev. 31 (2002) 22-36.
11. A. Satake, Y. Kobuke, Dynamic supramolecular porphyrin systems, Tetrahedron 61 (2005) 13-41. (Pubitemid 39573400)
12. T. Konishi, A. Ikeda, S. Shinkai, Supramolecular design of photocurrent-generating devices using fullerenes aimed at modelling artificial photosynthesis, Tetrahedron 61 (2005) 4881- 4899. (Pubitemid 40614938)
13. G. Kodis, Y. Terazono, P.A. Liddell, J. Andreasson, V. Garg, M. Hambourger, T.A. Moore, A.L. Moore, D. Gust, Energy and photoinduced electron transfer in a wheel-shaped artificial photosynthetic antenna-reaction center complex, J. Am. Chem. Soc. 128 (2006) 1818-1827. (Pubitemid 43277320)
14. D.I. Schuster, P.D. Jarowski, A.N. Kirschner, S.R. Wilson, Molecular modelling of fullerene-porphyrin dyads, Mater. Chem. 12 (2002) 2041-2047.
15. D. Gust, T.A. Moore, A.L. Moore, S.J. Lee, E. Bittersmann, D.K. Luttrull, A.A. Rehms, J.M. DeGraziano, X.C. Ma, Efficient multistep photoinitiated electron transfer in a molecular pentad, Science 248 (1990) 199-201. (Pubitemid 120031447)
16. F. D'Souza, E. Maligaspe, P. Karr, A.L. Schumacher, M. El Ojaimi, C.P. Gros, J.M. Barbe, K. Ohkubo, S. Fukuzumi, Face-to-face pacman-type porphyrin-fullerene dyads: design, synthesis, charge-transfer interactions, and photophysical studies, Chem. Eur. J. 14 (2008) 674-681.
17. S.A. Vail, P.J. Krawczuk, D.M. Guldi, A. Palkar, L. Echegoyen, C.J.P. Tome, M.A. Fazio, D.I. Schuster, Energy and electron transfer in polyacetylene-linked zinc-porphyrin- [60]fullerene molecular wires, Chem. Eur. J. 11 (2005) 3375-3388. (Pubitemid 40750995)
18. S.A. Vail, D.I. Schuster, D.M. Guldi, M. Isosomppi, N. Tkachenko, H. Lemmetyinen, A. Palkar, L. Echegoyen, X. Chen, J.Z.H. Zhang, Energy and electron transfer in b-alkynyl-linked porphyrin- [60]fullerene dyads, J. Phys. Chem. B 110 (2006) 14155-14166. (Pubitemid 44187974)
19. S. MacMahon, R. Fong II, P.S. Baran, I. Safonov, S.R. Wilson, D.I. Schuster, Synthetic approaches to a variety of covalently linked porphyrin-fullerene hybrids, J. Org. Chem. 66 (2001) 5449- 5455. (Pubitemid 32878898)
20. N. Armaroli, G. Marconi, L. Echegoyen, J.P. Bourgeois, F. Diederich, Charge-transfer interactions in face-to-face porphyrin-fullerene systems: solvent-dependent luminescence in the infrared spectral region, Chem. Eur. J. 6 (2000) 1629-1645.
21. C. Luo, D.M. Guldi, H. Imahori, K. Tamaki, Y. Sakata, Sequential energy and electron transfer in an artificial reaction center: formation of a long-lived charge-separated state, J. Am. Chem. Soc. 122 (2000) 6535-6551. (Pubitemid 30489971)
22. H. Imahori, K. Tamaki, D.M. Guldi, C. Luo, M. Fujitsuka, O. Ito, Y. Sakata, S. Fukuzumi, Modulating charge separation and charge recombination dynamics in porphyrin-fullerene linked dyads and triads: marcus-normal versus inverted region, Am. Chem. Soc. 123 (2001) 2607-2617. (Pubitemid 32888562)
23. H.J. Kim, K.M. Park, T.K. Ahn, S.K. Kim, K.S. Kim, D. Kim, H.J. Kim, Novel fullerene-porphyrin-fullerene triad linked by metal axial coordination: Synthesis, X-ray crystal structure, and spectroscopic characterizations of trans-bis( [60]fullerenoacetato)tin(IV) porphyrin, Chem. Commun. (2004) 2594-2595. (Pubitemid 39593335)
24. A.S.D. Sandanayaka, K. Ikeshita, Y. Araki, N. Kihara, Y. Furusho, T. Takata, O. Ito, Photoinduced electron- and energy-transfer processes of [60]fullerene covalently bonded with one and two zinc porphyrin(s): effects of coordination of pyridine and diazabicyclooctane to Zn atom, J. Mater. Chem. 15 (2005) 2276- 2287. (Pubitemid 40891941)
25. D.M. Guldi, C.P. Luo, M. Prato, A. Troisi, F. Zerbetto, M. Scheloske, E. Dietel, W. Bauer, A. Hirsch, 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, J. Am. Chem. Soc. 123 (2001) 9166-9167. (Pubitemid 32884740)
26. H. Xu, J. Zheng, Face-to-face alignment of porphyrin/fullerene nanowires linked by axial metal coordination macromol, Chem. Phys 211 (2010) 2125-2131.
27. M.J. Shephard, M.N. Paddon-Row, The porphyrin-C60 non-bonded interaction: An ab initio MO and DFT study, J. Porphyrins Phthalocyanines 6 (2002) 783-794.