Modulating electronic interactions between closely spaced complementary p surfaces with different outcomes: Regio- and diastereomerically pure subphthalocyanine-C60 tris adducts

Angewandte Chemie - International Edition

Volumn 48, Issue 43, 2009, Pages 8032-8036

  Gonzalez Rodriguez, David ^b   Carbonell, Esther ^a   Guldi, Dirk M ^a   Torres, Tomas ^b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

interactions; Electron transfer; Energy transfer; Fullerenes; Subphthalocyanines

Indexed keywords

DIFFERENT MECHANISMS; ELECTRON TRANSFER; ELECTRONIC INTERACTIONS; SPACE-FILLING; SUBPHTHALOCYANINES; TIGHTLY-COUPLED; TRIS-ADDUCTS;

ELECTRON TRANSITIONS; FULLERENES; ISOMERS; PHOTOEXCITATION;

ENERGY TRANSFER;

FULLERENE DERIVATIVE; INDOLE DERIVATIVE; PHTHALOCYANINE;

ARTICLE; CHEMISTRY; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ELECTRON TRANSPORT; FULLERENES; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 70349976463     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902767     Document Type: Article

References (49)

1. Handbook of Organic Electronics and Photonics (Ed.: H. S. Nalwa), American Scientific Publishers, New York, 2008.
2. S. Guenes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324-1338.
3. Molecular Mechanisms of Photosynthesis (Ed.: R. E. Blanken-ship), Blackwell, Oxford, 2002.
4. H. Imahori, H. Yamada, D. M. Guldi, Y. Endo, A. Shimomura, S. Kundu, K. Yamada, T. Okada, Y. Sakata, S. Fukuzumi, Angew. Chem. 2002, 114, 2450-2453;
5. Angew.Chem.Int.Ed. 2002, 41, 2344-2347.
6. Y. Araki, O. Ito, J. Photochem. Photobiol. C 2008, 9, 93-110.
7. D. M. Guldi, A. Hirsch, M. Scheloske, E. Dietel, A. Troisi, F. Zerbetto, M. Prato, Chem. Eur. J. 2003, 9, 4968-4979.
8. B. Albinsson, M. P. Eng, K. Pettersson, M. U. Winters, Phys. Chem. Chem. Phys. 2007, 9, 5847-5864.
9. A. Harriman, Angew. Chem. 2004, 116, 5093-5095;
10. Angew. Chem. Int. Ed. 2004, 43, 4985-4987.
11. G. Feher, J. P. Allen, M. Y. Okamura, D. C. Rees, Nature 1989, 339, 111-114.
12. a) D. Veldman, S. M. A. Chopin, S. C. J. Meskers, M. M. Groe-neveld, R. M. Williams, R. A. J. Janssen, J. Phys. Chem. A 2008, 112, 5846-5857;
13. b) J. M. Giaimo, J. V. Lockard, L. E. Sinks, A. M. Scott, T. M. Wilson, M. R. Wasielewski, J. Phys. Chem. A 2008, 112, 2322-2330.
14. a) C. G. Claessens, D. Gonzalez-RodriguezT. Torres, Chem. Rev. 2002, 102, 835-853;
15. b) T. Torres, Angew. Chem. 2006, 118, 2900-2903
16. Angew. Chem. Int. Ed. 2006, 45, 2834-2837.
17. SubPcs have been employed as energy donors, [12abd] electron donors, [12ad] and electron acceptors:[12bc] a) D. Gonzalez-Rodri-guez, T. Torres, D. M. Guldi, J. Rivera, M. A. Herranz, L. Echegoyen, J. Am. Chem. Soc. 2004, 126, 6301-6313;
18. b) D. Gonzalez-Rodriguez, C. G. Claessens, T. Torres, S.-G. Liu, L. Echegoyen, N. Vila, S. Nonell, Chem. Eur. J. 2005, 11, 3881-3893;
19. c) D. Gonzalez-Rodriguez, T. Torres, M. M. Olmstead, J. Rivera, M. A. Herranz, L. Echegoyen, C. Atienza-CastellanosD. M. Guldi, J. Am. Chem. Soc. 2006, 128, 10680-10681;
20. d) D. Gonzalez-Rodriguez, T. Torres, M. A. Herranz, L. Echegoyen, E. Carbonell, D. M. Guldi, Chem. Eur. J. 2008, 14, 7670-7679.
21. CG. Claessens, T. Torres, Chem. Commun. 2004, 1298-1299.
22. For recent reviews on multiple additions to fullerenes, see : a) C. Thilgen, S. Sergeyev, F. Diederich, Top. Curr. Chem. 2004, 248, 1-61;
23. b) A. Hirsch, Chem. Rec. 2005, 5, 196-208;
24. c) Z. Zhou, S. R. Wilson, Curr. Org. Chem. 2005, 9, 789-811.
25. Porphyrin-C60 systems connected through a double tether have been studied. See reference [6] and a) N. Armaroli, G Marconi, L. Echegoyen, J.-P. Bourgeois, F Diederich, Chem. Eur. J. 2000, 6, 1629-1645;
26. b) D. M. Guldi, C. Luo, M. Prato, A. Troisi, F Zerbetto, M. Scheloske, E. Dietel, W Bauer, A. Hirsch, J. Am. Chem. Soc. 2001, 123, 9166-9167.
27. Phthalocyanine-C60 systems connected through a double tether have also been studied: M. Niemi, N. V. Tkachenko, A. Efimov, H. K. Ohkubo, S. Fukuzumi, H. Lemmetyinen, J. Phys. Chem. A 2008, 112, 6884-6892.
28. a) G Rapenne, J. Crassous, A. Collet, L. Echegoyen, F Diederich, Chem. Commun. 1999, 1121-1122;
29. b) U. Reuther, T. Brandmüller, W Donaubauer, F. Hampel, A. Hirsch, Chem. Eur. J. 2002, 8, 2261-2273;
30. c) N. Chronakis, A. Hirsch, Chem. Commun. 2005, 3709-3711.
31. See Supporting Information for further details.
32. For the sake of simplicity and clarity, we use the terminology : c for cis, e for equatorial, and t for trans : L. Pasimeni, A. Hirsch, I. Lamparth, M. Maggini, M. Prato, J. Am. Chem. Soc. 1997, 119, 12902-12905.
33. The formation of the t4, t4, t4 tris-adition pattern is, moreover, highly electronically unfavorable: S-C Chuang, S. I. Khan, Y. Rubin, Org. Lett. 2006, 8, 6075-6078.
34. A t3, t3, t4 regioisomer can impose a different conformation on one of the biphenyl moieties in which a carbonyl group of the malonate moiety is close to the a proton of one of the isoindole units, which would explain the unusual downfield shift (> 0.5 ppm) of the proton signal around 9.4 ppm (see Figure 1 and Supporting Information).
35. The benzene dimer in its parallel-displaced configuration is held at a distance of 3.6 Â. See, for instance: T. Sato, T. Tsuneda, K. J. Hirao, J. Chem. Phys. 2005, 123, 104307.
36. Distances as short as 3.1-3.4 A have been observed in fullerene host-guest complexes: a) A. Sygula, F R. Fronczek, R. Sygula, P. W. Rabideau, M. M. Olmstead, J. Am. Chem. Soc. 2007, 129, 3842-3843;
37. b) E. M. Perez, M. Sierra, L. Sanchez, M. R. Torres, R. Viruela, P. M. Viruela, E. Orti, N. Martin, Angew. Chem. 2007, 119, 1879-1883;
38. Angew. Chem. Int. Ed. 2007, 46, 1847-1851;
39. c) G Fernandez, E. M. Perez, L. Sanchez, N. Martin, Angew. Chem. 2008, 120, 1110-1113;
40. Angew. Chem. Int. Ed. 2008, 47, 1094-1097;
41. d) E. M. Perez, A. L. Capodilupo, G. Fernandez, L. Sanchez, P. M. Viruela, R. Viruela, E. Orti, M. Bietti, N. Martin, Chem. Commun. 2008, 4567-4569;
42. e) E. M. Perez, N. Martin, Chem. Soc. Rev. 2008, 37, 1512-1519;
43. f) S. Gayathri, M. Wielopolski, E. M. Perez, G. Fernandez, L. Sanchez, R. Viruela, E. Orti, D M. Guldi, N. Martin, Angew. Chem. 2009, 121, 829-834;
44. Angew. Chem. Int. Ed. 2009, 48, 815-819.
45. The corresponding rate constants of SubPc singlet excited-state deactivation are 9.5x1010s~1 (1Ca) and 6.7x1010s-1 (1O) in THF
46. In fluorescence lifetime measurements a lifetime of 1.7 ns was registered for C60 fluorescence.
47. D M. Guldi, M. Prato, Acc. Chem. Res. 2000, 33, 695-703.
48. In fact, DFT calculations localize the phenoxyl HOMO very close in energy to the SubPc HOMO (see Figure S15, Supporting Information).
49. Calculated as the sum of the absolute values of the first oxidation potentials of the SubPc and the first reduction potentials of C60 (see Table 1).