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Volumn 61, Issue 15, 1996, Pages 5055-5062

Photoinduced electron transfer to C60 across extended 3- and 11-bond hydrocarbon bridges: Creation of a long-lived charge-separated state

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EID: 3743143974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960678q     Document Type: Article
Times cited : (203)

References (48)
  • 8
    • 0001515746 scopus 로고
    • (b) For a review of the photophysical properties of the fullerenes, see: Foote, C. S. In Top. Curr. Chem. 1994, 169, 347.
    • (1994) Top. Curr. Chem. , vol.169 , pp. 347
    • Foote, C.S.1
  • 11
    • 0342677835 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1994) J. Am. Chem. Soc. , vol.115 , pp. 9798
    • Maggini, M.1    Scorrano, G.2    Prato, M.3
  • 12
    • 0000405497 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4919
    • Kahn, S.I.1    Oliver, A.M.2    Paddon-Row, M.N.3    Rubin, Y.4
  • 13
    • 0000157792 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1993) Adv. Mater. , vol.5 , pp. 854
    • Belik, P.1    Gügel, A.2    Kraus, A.3    Spickermann, J.4    Enkelmann, V.5    Frank, G.6    Müllen, K.7
  • 14
    • 37049069092 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 589
    • Maggini, M.1    Karlsson, A.2    Scorrano, G.3    Sandonà, G.4    Farnia, G.5    Prato, M.6
  • 15
    • 33748233849 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1087
    • Beer, E.1    Feuerer, M.2    Knorr, A.3    Mirlach, A.4    Daub, J.5
  • 16
    • 37049083678 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1929
    • Iyoda, M.1    Sultana, F.2    Sasaki, S.3    Yoshida, M.4
  • 17
    • 37049079557 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 781
    • Diederich, F.1    Dietrich-Buchecker, C.2    Nierengarten, J.-F.3    Sauvage, J.-P.4
  • 18
    • 0002187517 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 845
    • Maggini, M.1    Donnò, A.2    Scorrano, G.3    Prato, M.4
  • 19
    • 37049076383 scopus 로고
    • Donor-Acceptor systems containing fullerenes: (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1994, 115, 9798. (b) Kahn, S. I.; Oliver, A. M.; Paddon-Row, M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919. (c) Belik, P.; Gügel, A.; Kraus, A.; Spickermann, J.; Enkelmann, V.; Frank, G.; Müllen, K. Adv. Mater. 1993, 5, 854. (d) Maggini, M.; Karlsson, A.; Scorrano, G.; Sandonà, G.; Farnia, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1994, 589. (e) Beer, E.; Feuerer, M.; Knorr, A.; Mirlach, A.; Daub, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1087. (f) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929. (g) Diederich, F.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; J. Chem. Soc., Chem. Commun. 1995, 781. (h) Maggini, M.; Donnò, A.; Scorrano, G.; Prato, M. J. Chem. Soc., Chem. Commun. 1995, 845. (i) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 103
    • Linssen, T.G.1    Dürr, K.2    Hanack, M.3    Hirsch, A.4
  • 22
    • 3743097229 scopus 로고    scopus 로고
    • note
    • The length of the bridge is taken to be the number of saturated bonds connecting the π-systems of the two chromophores. Thus, one of the saturated bonds of the fullerene cage is also included in the count. In the accompanying paper, only the length of the actual norbornylogous bridge was counted.
  • 29
    • 85030364705 scopus 로고    scopus 로고
    • Wavefunction Inc.; 18401 Von Karman Ave, Suite 370, Irvine, CA 92715
    • SPARTAN version 4.0.1; Wavefunction Inc.; 18401 Von Karman Ave, Suite 370, Irvine, CA 92715.
    • SPARTAN Version 4.0.1
  • 31
    • 85088622044 scopus 로고
    • private communication
    • -1 was observed; private communication from A. H. A. Clayton and K. P. Ghiggino, 1995.
    • (1995)
    • Clayton, A.H.A.1    Ghiggino, K.P.2
  • 34
    • 3743105006 scopus 로고    scopus 로고
    • note
    • The conformation shown in Figure 5 is the lowest energy conformation; however another conformation is possible, which is slightly higher in energy, see accompanying paper in this issue.
  • 36
    • 0347462845 scopus 로고
    • It should be noted that the occurrence of charge separation in 1,4-dioxane once more testifies the high micropolarity of this quadrupolar solvent, see: Suppan, P. J. Photochem. Photobiol. A 1990, 50, 293.
    • (1990) J. Photochem. Photobiol. A , vol.50 , pp. 293
    • Suppan, P.1
  • 37
    • 85088620735 scopus 로고    scopus 로고
    • note
    • -1.


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