Cyclo[8]pyrrole: An androgynous expanded porphyrin that acts as both an electron donor and acceptor in anion-bound supramolecular electron donor-acceptor complexes

Journal of Physical Chemistry C

Volumn 118, Issue 32, 2014, Pages 18436-18444

  Ohkubo, Kei ^a   Mase, Kentaro ^a   Karnas, Elizabeth ^b   Sessler, Jonathan L ^b   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CARBOXYLATION; CHARGE TRANSFER; ELECTRON TRANSITIONS; EXCITED STATES; FREE RADICAL REACTIONS; HYDROGEN BONDS; NEGATIVE IONS; PHOTOEXCITATION; PORPHYRINS; SUPRAMOLECULAR CHEMISTRY; ZINC COMPOUNDS;

ASSOCIATION CONSTANT; CHARGE-SEPARATED STATE; ELECTRON DONOR ACCEPTORS; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOINDUCED CHARGE SEPARATION; SINGLET EXCITED STATE; SUPRAMOLECULAR COMPLEXES; TRANSIENT ABSORPTION;

SEPARATION;

EID: 84906249005     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp505750e     Document Type: Article

References (54)

1. Fukuzumi, S. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 1999; Vol. 8, pp 115-151.
2. Harvey, P. D.; Stern, C.; Guilard, R. Bio-inspired Molecular Devices Based on Systems Found in Photosynthetic Bacteria. In Handbook of Porphyrin Science; Kadish, K. M., Smith, K. M., Guilard, R., Ed.; World Scientific Publishing Co. Ltd.: Singapore, 2011; Vol. 11, pp 1-179.
3. Fukuzumi, S. Artificial Photosynthetic Systems Composed of Porphyrins and Phthalocyanines. In Handbook of Porphyrin Science; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; World Scientific Publishing Co. Ltd.: Singapore, 2010, Vol. 10; pp 183-243.
4. Gust, D.; Moore, T. A.; Moore, A. L. Covalently Linked Systems Containing Porphyrin Units. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3, pp 272-336.
5. Langford, S. J.; Latter, M. J.; Woodward, C. P. Progress in Charge Transfer Systems Utilizing Porphyrin Donors and Simple Aromatic Diimide Acceptor Units Photochem. Photobiol. 2006, 82, 1530-1540
6. Fukuzumi, S. Bioinspired Electron-Transfer Systems and Applications Bull. Chem. Soc. Jpn. 2006, 79, 177-195
7. Gust, D.; Moore, T. A.; Moore, A. L. Solar Fuels via Artificial Photosynthesis Acc. Chem. Res. 2009, 42, 1890-1898
8. Fukuzumi, S. Development of Bioinspired Artificial Photosynthetic Systems Phys. Chem. Chem. Phys. 2008, 10, 2283-2297
9. Wasielewski, M. R. Self-Assembly Strategies for Integrating Light Harvesting and Charge Separation in Artificial Photosynthetic Systems Acc. Chem. Res. 2009, 42, 1910-1921
10. Wrobel, D.; Graja, A. Photoinduced Electron Transfer Processes in Fullerene-Organic Chromophore Systems Coord. Chem. Rev. 2011, 255, 2555-2577
11. Fukuzumi, S.; Honda, T.; Ohkubo, K.; Kojima, T. Charge Separation in Metallomacrocycle Complexes Linked with Electron Acceptors by Axial Coordination Dalton Trans. 2009, 3880-3889
12. Griffith, M. J.; Sunahara, K.; Wagner, P.; Wagner, K.; Wallace, G. G.; Officer, D. L.; Furube, A.; Katoh, R.; Mori, S.; Mozer, A. J. Porphyrins for Dye-Sensitized Solar Cells: New Insights into Efficiency-Determining Electron Transfer Steps Chem. Commun. 2012, 48, 4145-4162
13. Fukuzumi, S.; Ohkubo, K. Assemblies of Artificial Photosynthetic Reaction Centers J. Mater. Chem. 2012, 22, 4575-4587
14. de la Torre, G.; Bottari, G.; Sekita, M.; Hausmann, A.; Guldi, D. M.; Torres, T. A Voyage into the Synthesis and Photophysics of Homo- and Heterobinuclear Ensembles of Phthalocyanines and Porphyrins Chem. Soc. Rev. 2013, 42, 8049-8105
15. Li, L.-L.; Diau, W.-G. E. Porphyrin-Sensitized Solar Cells Chem. Soc. Rev. 2013, 42, 291-304
16. El-Khouly, M. E.; Fukuzumi, S.; D'Souza, F. Photosynthetic Antenna-Reaction Center Mimicry by Using Boron Dipyrromethene Sensitizer ChemPhysChem 2014, 15, 30-47
17. Fukuzumi, S.; Ohkubo, K.; Suenobu, T. Long-Lived Charge Separation and Applications in Artificial Photosynthesis Acc. Chem. Res. 2014, 47, 1455-1464
18. Kadish, K. M.; Morrison, M. M. Solvent and Substituent Effects on the Redox Reactions of Para-Substituted Tetraphenylporphyrin J. Am. Chem. Soc. 1976, 98, 3326-3328
19. Terazono, Y.; Dolphin, D. Synthesis and Characterization of β-Trifluoromethyl- meso -Tetraphenylporphyrins J. Org. Chem. 2003, 68, 1892-1900
20. Gould, S. L.; Kodis, G.; Palacios, R. E.; de la Garza, L.; Brune, A.; Gust, D.; Moore, T. A.; Moore, A. L. Artificial Photosynthetic Reaction Centers with Porphyrins as Primary Electron Acceptors J. Phys. Chem. B 2004, 108, 10566-10580
21. II Complexes: The Effect of Metalation and Structural Variation Chem.-Eur. J. 2013, 19, 338-349
22. Fukuzumi, S.; Honda, T.; Kojima, T. Structures and Electron-Transfer Properties of Protonated Complexes of Porphyrins and Metallophthalocyanines Coord. Chem. Rev. 2012, 256, 2488-2502
23. Kojima, T.; Honda, T.; Ohkubo, K.; Shiro, M.; Kusukawa, T.; Fukuda, T.; Nagao, K.; Fukuzumi, S. A Discrete Supramolecular Conglomerate Composed of Two Saddle-Distorted Zinc(II)-Phthalocyanine Complexes and a Doubly Protonated Porphyrin with Saddle-Distortion Undergoing Efficient Photoinduced Electron Transfer Angew. Chem., Int. Ed. 2008, 47, 6712-6716
24. Honda, T.; Nakanishi, T.; Ohkubo, K.; Kojima, T.; Fukuzumi, S. Structure and Photoinduced Electron Transfer Dynamics of a Series of Hydrogen-Bonded Supramolecular Complexes Composed of Electron Donors and a Saddle-Distorted Diprotonated Porphyrin J. Am. Chem. Soc. 2010, 132, 10155-10163
25. D'Souza, F.; Ito, O. Photoinduced Electron Transfer in Supramolecular Systems of Fullerenes Functionalized with Ligands Capable of Binding to Zinc Porphyrins and Zinc Phthalocyanines Coord. Chem. Rev. 2005, 249, 1410-1422
26. Kojima, T.; Nakanishi, T.; Honda, T.; Fukuzumi, S. Photoinduced Electron Transfer in Supramolecular Assemblies Involving Saddle-Distorted Porphyrins and Phthalocyanines J. Porphyrins Phthalocyanines 2009, 13, 14-21
27. Fukuzumi, S.; Ohkubo, K. Long-Lived Photoinduced Charge Separation for Solar Cell Applications in Supramolecular Complexes of Multi-Metalloporphyrins and Fullerenes Dalton Trans. 2013, 42, 15846-15858
28. Chitta, R.; D'Souza, F. Self-Assembled Tetrapyrrole-Fullerene and Tetrapyrrole-Carbon Nanotube Donor-Acceptor Hybrids for Light Induced Electron Transfer Applications J. Mater. Chem. 2008, 18, 1440-1471
29. D'Souza, F.; Ito, O. Supramolecular Donor-Acceptor Hybrids of Porphyrins/ Phthalocyanines with Fullerenes/Carbon Nanotubes: Electron Transfer, Sensing, Switching, and Catalytic Applications Chem. Commun. 2009, 4913-4928
30. Fukuzumi, S.; Ohkubo, K.; D'Souza, F.; Sessler, J. L. Supramolecular Electron Transfer by Anion Binding Chem. Commun. 2012, 48, 9801-9815
31. Poddutoori, P. K.; Zarrabi, N.; Moiseev, A. G.; Gumbau-Brisa, R.; Vassiliev, S.; van der Est, A. Long-Lived Charge Separation in Novel Axial Donor-Porphyrin-Acceptor Triads Based on Tetrathiafulvalene, Aluminum (III) Porphyrin, and Naphthalenediimide Chem.-Eur. J. 2013, 19, 3148-3161
32. Stranius, K.; Iashin, V.; Nikkonen, T.; Muuronen, M.; Helaja, J.; Tkachenko, N. Effect of Mutual Position of Electron Donor and Acceptor on Photoinduced Electron Transfer in Supramolecular Chlorophyll-Fullerene Dyads J. Phys. Chem. A 2014, 118, 1420-1429
33. Sessler, J. L.; Seidel, D. Synthetic Expanded Porphyrin Chemistry Angew. Chem. 2003, 115, 5292-5333
34. Angew. Chem., Int. Ed. 2003, 42, 5134-5175.
35. Seidel, D.; Lynch, V.; Sessler, J. L. Cyclo[8]pyrrole: A Simple-to-Make Expanded Porphyrin with No Meso Bridges Angew. Chem., Int. Ed. 2002, 41, 1422-1425
36. Kohler, T.; Seidel, D.; Lynch, V.; Arp, F. O.; Ou, Z.; Kadish, K. M.; Sessler, J. L. Formation and Properties of Cyclo[6]pyrrole and Cyclo[7]pyrrole J. Am. Chem. Soc. 2003, 125, 6872-6873
37. Karnas, E.; Kim, S. K.; Johnson, K. A.; Sessler, J. L.; Ohkubo, K.; Fukuzumi, S. Stopped-Flow Kinetic Analysis of the Interaction of Cyclo[8]pyrrole with Anions J. Am. Chem. Soc. 2010, 132, 16617-16622
38. Sessler, J. L.; Karnas, E.; Kim, S. K.; Ou, Z.; Zhang, M.; Kadish, K. M.; Ohkubo, K.; Fukuzumi, S. "Umpolung" Photoinduced Charge Separation in an Anion-Bound Supramolecular Complex J. Am. Chem. Soc. 2008, 130, 15256-15257
39. Matile, S.; Berova, N.; Nakanishi, K. Porphyrins: Powerful Chromophores for Structural Studies by Exciton-Coupled Circular Dichroism J. Am. Chem. Soc. 1995, 117, 7021-7022
40. Mann, C. K.; Barnes, K. K. In Electrochemical Reactions in Non-Aqueous Systems; Mercel Dekker: New York, 1970.
41. Frisch, M. J.; Gaussian 09, revision A.03; Gaussian, Inc., Wallingford CT, 2009, (full author list is given in the Supporting Information).
42. Becke, A. D. A Multicenter Numerical Integration Scheme for Polyatomic Molecules J. Chem. Phys. 1988, 88, 2547-2553
43. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
44. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior Phys. Rev. A 1988, 38, 3098-3100
45. Dennington, R., II; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. GaussView; Semichem: Shawnee Mission, KS, 2003.
46. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. An Efficient Implementation of Time-Dependent Density-Functional Theory for the Calculation of Excitation Energies of Large Molecules J. Chem. Phys. 1998, 109, 8218-8224
47. 60 with NADH and NAD Dimer Analogues via Photoinduced Electron Transfer J. Am. Chem. Soc. 1998, 120, 8060-8068
48. 60 J. Am. Chem. Soc. 2011, 133, 15938-15941
49. Davis, C. M.; Kawashima, Y.; Ohkubo, K.; Lim, J. M.; Kim, D.; Fukuzumi, S.; Sessler, J. L. Photoinduced Electron Transfer from a Tetrathiafulvalene- Calix[4]pyrrole to a Porphyrin Carboxylate within a Supramolecular Ensemble J. Phys. Chem. C 2014, 118, 13503-13513
50. 60 with Sulfonated meso -Tetraphenylporphyrins and Long-Lived Photoinduced Charge Separation Chem. Commun. 2012, 48, 4314-4316
51. Park, J. S.; Karnas, E.; Ohkubo, K.; Chen, P.; Kadish, K. M.; Fukuzumi, S.; Bielawski, C. W.; Hudnall, T. W.; Lynch, V. M.; Sessler, J. L. Ion-Mediated Electron Transfer in a Supramolecular Donor-Acceptor Ensemble Science 2010, 329, 1324-1327
52. 60 Affording the Long-Lived Charge-Separated State J. Phys. Chem. C 2013, 117, 21166-21177
53. 60 Dyad Produced by One-Step Photoinduced Electron Transfer Angew. Chem., Int. Ed. 2004, 43, 853-856
54. Marcus, R. A.; Sutin, N. Electron Transfers in Chemistry and Biology Biochim. Biophys. Acta 1985, 811, 265-322