Monoisomeric phthalocyanines and phthalocyanine-fullerene dyads with polar side chains: Synthesis, modeling, and photovoltage

Journal of Physical Chemistry C

Volumn 118, Issue 5, 2014, Pages 2754-2765

  Ranta, Jenni ^a   Kaunisto, Kimmo ^a   Niskanen, Mika ^a   Efimov, Alexander ^a   Hukka, Terttu I ^a   Lemmetyinen, Helge ^a  

^a TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SUBPHASE; DISPLACEMENT CHARGE; ELECTRON ACCEPTOR; ELECTRON TRANSFER; MUTUAL ORIENTATION; PHOTOVOLTAGE RESPONSE; POLAR SIDE CHAINS; SPATIAL ARRANGEMENTS;

ELECTRON TRANSITIONS; FULLERENES; MOLECULAR MODELING; MONOLAYERS;

NITROGEN COMPOUNDS;

EID: 84893834897     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp4096002     Document Type: Article

References (71)

1. Martínez-Díaz, M. V.; de la Torre, G.; Torres, T. Lightning Porphyrins and Phthalocyanines for Molecular Photovoltaics Chem. Commun. 2010, 46, 7090-7108
2. de la Torre, G.; Claessens, C. G.; Torres, T. Phthalocyanines: The Need for Selective Synthetic Approaches Eur. J. Org. Chem. 2000, 2821-2830
3. Görlach, B.; Dachtler, M.; Glaser, T.; Albert, K.; Hanack, M. Synthesis and Separation of Structural Isomers of 2(3),9(10), 16(17),23(24)-Tetrasubstituted Phthalocyanines Chem.-Eur. J. 2001, 7, 2459-2465 (Pubitemid 33028916)
4. de la Torre, G.; Claessens, C. G.; Torres, T. Phthalocyanines: Old Dyes, New Materials. Putting Color in Nanotechnology Chem. Commun. 2007, 2000-2015 (Pubitemid 46964320)
5. Mack, J.; Kobayashi, N. Low Symmetry Phthlocyanines and Their Analogues Chem. Rev. 2011, 111, 281-321
6. Martínez-Díaz, M. V.; Ince, M.; Torres, T. Phthalocyanines: Colorful Macroheterocyclic Sensitizers for Dye-Sensitized Solar Cells Monatsh. Chem. 2011, 142, 699-707
7. Kobayashi, N.; Ogata, H.; Nonaka, N.; Luḱyanets, E. A. Effect of Perpheral Substitution on the Electronic Absorption and Fluorescence Spectra of Metal-Free and Zinc Phthalocyanines Chem.-Eur. J. 2003, 9, 5123-5134
8. Prato, M. [60]Fullerene Chemistry for Materials Science Applications J. Mater. Chem. 1997, 7, 1097-1109 (Pubitemid 127731260)
9. Lehtivuori, H.; Kumpulainen, T.; Efimov, A.; Lemmetyinen, H.; Kira, A.; Imahori, H.; Tkachenko, N. V. Photoinduced Electron Transfer in Langmuir-Blodgett Monolayers of Double-Linked Phthalocyanine-Fullerene Dyads J. Phys. Chem. C 2008, 112, 9896-9902
10. Guldi, D. M.; Gouloumis, A.; Vázquez, P.; Torres, T. Charge-Transfer States in Strongly Coupled Phthalocyanine fullerene ensembles Chem. Commun. 2002, 2056-2057 (Pubitemid 35221338)
11. Ince, M.; Martínez-Díaz, M. V.; Barberá, J.; Torres, T. Liquid Crystalline Phthalocyanine-Fullerene Dyads J. Mater. Chem. 2011, 21, 1531-1536
12. Bottari, G.; Trukhina, O.; Torres, T. Towards Artificial Photosynthesis: Supramolecular, Donor-Acceptor, Porphyrin- and Phthalocyanine/Carbon Nanostructure Ensembles Coord. Chem. Rev. 2012, 256, 2453-2477
13. Claessens, C. G.; Hahn, U.; Torres, T. Phthalocyanines: From Outstanding Electronic Properties to Emerging Applications Chem. Rec. 2008, 8, 75-97
14. Gouloumis, A.; Liu, S.-G.; Sastre, á.; Vázquez, P.; Echegoyen, L.; Torres, T. Synthesis and Electrochemical Properties of Phthalocyanine-Fullerene Hybrids Chem.-Eur. J. 2000, 6, 3600-3607
15. Niemi, M.; Tkachenko, N. V.; Efimov, A.; Lehtivuori, H.; Ohkubo, K.; Fukuzumi, S.; Lemmetyinen, H. Exciplex Mediated Photoinduced Electron Transfer Reactions of Phthalocyanine-Fullerene Dyads J. Phys. Chem. A 2008, 112, 6884-6892
16. Rodríguez-Morgade, M. S.; Plonska-Brzezinska, M. A.; Athans, A. J.; Carbonell, E.; de Miguel, G.; Guldi, D. M.; Echegoyen, L.; Torres, T. Synthesis, Characterization, and Photoinduced Electron Transfer Processes of Orthogonal Ruthenium Phthalocyanine-Fullerene Assemblies J. Am. Chem. Soc. 2009, 131, 10484-10496
17. de la Escosura, A.; Martínez-Díaz, V.; Guldi, D. M.; Torres, T. Stabilization of Charge-Separated States in Phthalocyanine-Fullerene Ensembles Through Supramolecular Donor-Acceptor Interactions J. Am. Chem. Soc. 2006, 128, 4112-4118
18. Pereira, A. M. V. M; Hausmann, A.; Tomé, J. P. C.; Trukhina, O.; Urbani, M.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S.; Guldi, D. M.; Torres, T. Chem.-Eur. J. 2012, 18, 3210-3219
19. D́Souza, F.; Maligaspe, E.; Sandanayaka, A. S. D.; Subbaiyan, N. K.; Karr, P. A.; Hasobe, T.; Ito, O. Photochemical Charge Separation in Supramolecular Phthalocyanine-Multifullerene Conjugares Assembled by Crown Ether-Alkyl Ammonium Cation Interactions J. Phys. Chem. A 2010, 114, 10951-10959
20. Hayashi, H.; Nihashi, W.; Umeyama, T.; Matano, Y.; Seki, S.; Shimizu, Y.; Imahori, H. Segregated Donor-Acceptor Columns in Liquid Crystal That Exhibit Highly Efficient Ambipolar Charge Transport J. Am. Chem. Soc. 2011, 133, 10736-10739
21. Imahori, H.; Umeyama, T.; Kurotobi, K.; Takano, Y. Self-Assembling Porphyrins and Phthalocyanines for Photoinduced Charge Separation and Charge Transport Chem. Commun. 2012, 48, 4032-4045
22. Bottari, G.; de la Torre, G.; Guldi, D. M.; Torres, T. Covalent and Noncovalent Phthalocyanine-Carbon Nanostructure Systems: Synthesis, Photoinduced Electron Transfer, and Application to Molecular Photovoltaics Chem. Rev. 2010, 110, 6768-6816
23. Lehtivuori, H.; Kumpulainen, T.; Hietala, M.; Efimov, A.; Lemmetyinen, H.; Kira, A.; Imahori, H.; Tkachenko, N. V. Photodynamics of Charge Separation and Recombination in Solid Alternating Films of Phthalocyanine or Phthalocyanine-Fullerene Dyad and Perylene Dicarboximide J. Phys. Chem. C 2009, 113, 1984-1992
24. Bikram, C. K. C.; Subbaiyan, N. K.; D́Souza, F. Supramolecular Donor-Acceptor Assembly Derived from Tetracarbazole-Zinc Phthalocyanine Coordinated to Fullerene: Design, Synthesis, Photochemical, and Photoelectrochemical Studies J. Phys. Chem. C 2012, 116, 11964-11972
25. Martín-Gomis, L.; Ohkubo, K.; Fernández-Lázaro, F.; Fukuzumi, S.; Sastre-Santos, á. Multistep Electron Transfer Systems Based on Silicon Phthalocyanine, [60]Fullerene and Trinitrofluorenone Chem. Commun. 2010, 46, 3944-3946
26. Liu, J.-Y.; Lo, P.-C.; Ng, D. K. P. Phthalocyanine-Containing Supramolecular Arrays Struct. Bonding (Berlin) 2010, 135, 169-210
27. Guldi, D. M.; Ramey, J.; Martínez-Díaz, V.; de la Escosura, A.; Torres, T.; Da Ros, T.; Prato, M. Reversible Zinc Phthalocyanine Fullerene Ensembles Chem. Commun. 2002, 2774-2775 (Pubitemid 35375674)
28. Neugebauer, H.; Loi, M. A.; Winder, C.; Sariciftci, N. S.; Cerullo, G.; Gouloumis, A.; Vázquez, P.; Torres, T. Photophysics and Photovoltaic Device Properties of Phthalocyanine-Fullerene Dyad: Conjugated Polymer Mixtures Sol. Energy Mater. Sol. Cells 2004, 83, 201-209
29. Guldi, D. M.; Zilbermann, I.; Gouloumis, A.; Vázquez, P.; Torres, T. Metallophthalocyanines: Versatile Electron-Donating Building Blocks for Fullerene Dyads J. Phys. Chem. B 2004, 108, 18485-18494
30. Ohkubo, K.; Fukuzumi, S. Long-Lived Charge-Separated States of Simple Electron Donor-Acceptor Dyads Using Porphyrins and Phthalocyanines J. Porphyrins Phthalocyanines 2008, 12, 993-1004
31. 80 (M = Y, Sc) Based Dyads: Synthesis, and Electrochemical, Theoretical and Photophysical Studies Chem.-Eur. J. 2009, 15, 864-877
32. Loi, M. A. Long-Lived Photoinduced Charge Separation for Solar Cell Applications in Phthalocyanine-Fulleropyrrolidine Dyad Thin Films J. Mater. Chem. 2003, 13, 700-704
33. Isosomppi, M.; Tkachenko, N. V.; Efimov, A.; Vahasalo, H.; Jukola, J.; Vainiotalo, P.; Lemmetyinen, H. Photoinduced Electron Transfer of Double-Bridged Phthalocyanine-Fullerene Dyads Chem. Phys. Lett. 2006, 430, 36-40 (Pubitemid 44465868)
34. Kc, C. B.; Ohkubo, K.; Karr, P. A.; Fukuzumi, S.; D́Souza, F. áTwo-Point́ Bound Zinc Porphyrin-Zinc Phthalocyanine-Fullerene Supramolecular Triad for Sequential Energy and Electron Transfer Chem. Commun. 2013, 49, 7614-7616
35. Lemmetyinen, H.; Kumpulainen, T.; Niemi, M.; Efimov, A.; Ranta, J.; Stranius, K.; Tkachenko, N. V. Independence and Inverted Dependence on Temperature of Rates of Photoinduced Electron Transfer in Double-Linked Phthalocyanine-Fullerene Dyads Photochem. Photobiol. Sci. 2010, 9, 949-959
36. 59N-Phthalocyanine Dyad: Synthesis, Characterisation and Photoinduced Electron Transfer ChemPhysChem 2012, 13, 1246-1254
37. 60 Supramolecular Dyad Tetrahedron 2006, 62, 2097-2101 (Pubitemid 43185986)
38. 70) J. Phys. Chem. A 1997, 101, 7943-7947 (Pubitemid 127609147)
39. Doyle, J. J.; Ballesteros, B.; de la Torre, G.; McGovern, D. A.; Kelly, J. M.; Torres, T.; Blau, W. J. Combination of Phthalocyanine and Fullerene Moieties for Optical Limiting Chem. Phys. Lett. 2006, 428, 307-311 (Pubitemid 44313888)
40. D'Souza, F.; Maligaspe, E.; Ohkubo, K.; Zandler, M. E.; Subbaiyan, N. K.; Fukuzumi, S. Photosynthetic Reaction Center Mimicry: Low Reorganization Energy Driven Charge Stabilization in Self-Assembled Cofacial Zinc Phthalocyanine Dimer-Fullerene Conjugate J. Am. Chem. Soc. 2009, 131, 8787-8797
41. Diacon, A.; Rusen, E.; Boscornea, C.; Pandele, A. M.; Cincu, C. New Phthalocyanine-Fullerene Dyads for Solar Cells U. P. B. Sci. Bull., Ser. B 2011, 73, 87-98
42. Shimizu, S.; Miura, A.; Kobayashi, N. Highly Deformed Phthalocyanine as a Suitable Scaffold for Pristine Fullerenes CrystEngComm 2013, 15, 3759-3762
43. 60)-Phthalocyanine Triad Org. Lett. 2006, 8, 5187-5190 (Pubitemid 44867306)
44. 60 Triad Org. Lett. 2007, 9, 3441-3444
45. El-Khouly, M. E.; Kim, J. H.; Kay, K.-Y.; Choi, C. S.; Ito, O.; Fukuzumi, S. Synthesis and Photoinduced Intramolecular Processes of Light-Harversting Silicon Phthalocyanine-Naphtalenediimide-Fullerene Connected Systems Chem.-Eur. J. 2009, 15, 4528-4533
46. de la Torre, G.; Bottari, G.; Hahn, U.; Torres, T. Functional Phthalocyanines: Synthesis, Nanosructuration, and Electro-Optical Applications Struct. Bonding (Berlin) 2010, 135, 1-44
47. Wenzel, J.; Dreuw, A.; Burqhardt, I. Charge and Energy Transfer in a Bithiophene Perylenediimide Based Donor-Acceptor-Donor System for Use in Organic Photovoltaics Phys. Chem. Chem. Phys. 2013, 15, 11704-11716
48. Lewandowska, K.; Barszcz, B.; Graja, A.; Bursa, B.; Biadasz, A.; Wróbel, D.; Bednarski, W.; Waplak, S.; Grzybowski, M.; Gryko, D. T. Absorption and Emission Properties of the Corrole-Fullerene Dyad Synth. Met. 2013, 166, 70-76
49. Cramariuc, O.; Hukka, T. I.; Rantala, T. T.; Lemmetyinen, H. Ab Initio Description of Photoabsorption and Electron Transfer in a Doubly-Linked Porphyrin-Fullerene Dyad J. Comput. Chem. 2009, 30, 1194-1201
50. Körzdöfer, T.; Tretiak, S.; Kümmel, S. Fluorescence Quenching in an Organic Donor-Acceptor Dyad: A First Principles Study J. Chem. Phys. 2009, 131, 034310:1-9
51. Tolkki, A.; Kaunisto, K.; Efimov, A.; Kivistö, H.; Storbacka, L.; Savikoski, R.; Huttunen, K.; Lehtimäki, S.; Lemmetyinen, H. Directed Electron Transfer in Langmuir-Schäfer Layers of Porphyrin-Fullerene and Phthalocyanine-Fullerene Dyads in Inverted Organic Solar Cells Phys. Chem. Chem. Phys. 2012, 14, 3498-3504
52. Vivo, P.; Ojala, M.; Chukharev, V.; Efimov, A.; Lemmetyinen, H. Role of a Phthalocyanine-Fullerene Dyad in Multilayered Organic Solar Cells J. Photochem. Photobiol., A 2009, 203, 125-130
53. Alekseev, A. S.; Efimov, A. V.; Chukharev, V. I.; Lemmetyinen, H. Directed Photocurrent in Langmuir-Schaefer Organic Molecular Films Bull. Lebedev Phys. Inst. 2010, 37, 136-140
54. Tkachenko, N. V.; Efimov, A.; Lemmetyinen, H. Covalent Phthalocyanine-Fullerene Dyads: Synthesis, Electron Transfer in Solutions and Molecular Films J. Porphyrins Phthalocyanines 2011, 15, 780-790
55. Imaoka, T.; Ueda, H.; Yamamoto, K. Enhancing the Photoelectric Effect with a Potential-Programmed Molecular Rectifier J. Am. Chem. Soc. 2012, 134, 8412-8415
56. 2) Phthalocyanine-Fullerene Dyads J. Org. Chem. 2010, 75, 5178-5194
57. Roberts, G. Langmuir-Blodgett Films; Plenum Press: New York, 1990.
58. Tkachenko, N. V.; Vuorimaa, E.; Kesti, T.; Alekseev, A. S.; Tauber, A. Y.; Hynninen, P. H.; Lemmetyinen, H. Vectorial Photoinduced Electron Transfer in Phytochlorin-[60]Fullerene Langmuir-Blodgett Films J. Phys. Chem. B 2000, 104, 6371-6379
59. Tkachenko, N. V.; Tauber, A. Y.; Hynninen, P. H.; Sharonov, A. Y.; Lemmetyinen, H. Light-Induced Electron Transfer in Pyropheophytin-Antraquinone Dyads: Vectorial Charge Transfer in Langmuir-Blodgett Films J. Phys. Chem. A 1999, 103, 3657-3665 (Pubitemid 129570869)
60. Vuorinen, T.; Kaunisto, K.; Tkachenko, N. V.; Efimov, A.; Lemmeyinen, H.; Alekseev, A. S.; Hosomizu, K.; Imahori, H. Photoinduced Electron Transfer in Langmuir-Blodgett Monolayers of Porphyrin-Fullerene Dyads Langmuir 2005, 21, 5383-5390 (Pubitemid 40850624)
61. Frisch, G. M. J.; Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2010.
62. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
63. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
64. Vosko, S. H.; Wilk, L.; Nusair, M. Accurate Spin-Dependent Electron Liquid Correlations for Local Spin Density Calculations: a Critical Analysis Can. J. Phys. 1980, 58, 1200-1211
65. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
66. 60 and Di(ethoxycarbonyl)methylene Angew. Chem., Int. Ed. Engl. 1994, 33 (No. 4) 437-438 (Pubitemid 24987369)
67. Zhurko, G. A. Chemcraft Version 1.60, available at www.chemcraftprog.com.
68. Kaunisto, K.; Chukharev, V.; Tkachenko, N. V.; Lemmetyinen, H. Long-Lived Charge Separated State in Molecular Films Containing Porphyrin-Fullerene Dyad Chem. Phys. Lett. 2008, 460, 241-244
69. Kaunisto, K.; Chukharev, V.; Tkachenko, N. V.; Efimov, A.; Lemmetyinen, H. Energy and Electron Transfer in Multilayer Films Containing Porphyrin-Fullerene Dyad J. Phys. Chem. C 2009, 113, 3819-3825
70. Kaunisto, K.; Vuorinen, T.; Vahasalo, H.; Chukharev, V.; Tkachenko, N. V.; Efimov, A.; Tolkki, A.; Lehtivuori, H.; Lemmetyinen, H. Photoinduced Electron Transfer and Photocurrent in Multicomponent Organic Molecular Films Containing Oriented Pophyrin-Fullerene Dyad J. Phys. Chem. C 2008, 112, 10256-10265
71. Kaunisto, K.; Vahasalo, H.; Chukharev, V.; Tkachenko, N. V.; Vivo, P.; Niemi, M.; Tolkki, A.; Efimov, A.; Lemmetyinen, H. Photoinduced Charge Transfer Through Films Containing Poly(hexylthiophene), Phthalocyanine, and Porphyrin-Fullerene Layers Thin Solid Films 2009, 517, 2988-2993