Photoinduced Electron Transfer between Mono-6-p-nitrobenzoyl-β-cyclodextrin and Adamantanamine-C n-porphyrins

Journal of Physical Chemistry B

Volumn 107, Issue 50, 2003, Pages 14087-14093

  Wang, Yong Hui ^a   Zhu, Man Zhou ^a   Ding, Xiao Yuan ^a   Ye, Jian Ping ^b   Liu, Lei ^a,d   Guo, Qing Xiang ^a,c  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c LANZHOU UNIVERSITY   (China)

^d Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ELECTROCHEMISTRY; ELECTRON TRANSPORT PROPERTIES; FLUORESCENCE; HYDROGEN BONDS; METHANOL; QUANTUM THEORY; QUENCHING; SUPRAMOLECULAR CHEMISTRY;

ELECTROCHEMICAL MEASUREMENTS; PHOTOINDUCED ELECTRON TRANSFER;

BENZENE;

EID: 0347567531     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0347419     Document Type: Article

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24. For recent examples, see: (a) Tsue, H.; Imahori, H.; Kaneda, T.; Tanaka, Y.; Okada, T.; Tamaki, K.; Sakata, Y. J. Am. Chem. Soc. 2000, 122, 2279, (b) Sun, J.; Liu, Y.; Cheng, D.-W.; Zhang, Q.-Y.; Li, F.-Y.; Li, Y.-L.i Zhu, D.-B.; Gan, L.-B.; Huang, C.-H. Acta Chim. Sin. 2000, 58, 786. (c) Jiang, H.; Xu, H. J. Chin. Chem. Lett. 2000, 11, 767. (d) Rajesh, C. S.; Capitosti, G. J.; Cramer, S. J.; Modarelli, D. A. J. Phys. Chem. B 2001, 105, 10175. (e) Lor, M.; Thielemans, J.; Viaene, L.; Collet, M.; Hofkens, J.; Weil, T.; Hampel, C.; Mullen, K.; Verhoeven, J. W.; Van der Auweraer, M.; De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918. (f) Ballardini, R.; Balzani, V.; Clemente-Leon, M.; Credi, A.; Gandolfi, M. T.; Elena, P. J.; Stoddart, J. F.; Tseng, H.-R. J. Am. Chem. Soc. 2002, 124, 12786. (g) Fukuzumi, S.; Okamoto, J.; Yoshida, Y.; Imahori, H.; Araki, Y.; Ito, O. J. Am. Chem. Soc. 2003, 125, 1007. (h) Zhang, H.-P.; Zhou, Y.-L.; Zhang, M.-H.; Shen, T.; Li, Y.-L.; Zhu, D.-B. Gaodeng Xuexiao Huaxue Xuebao 2003, 24, 492.
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28. For recent examples, see: (a) Williamson, D. A.; Bowler, B. E. J. Am. Chem. Soc. 1998, 120, 10902. (b) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143. (c) Smitha, M. A.; Prasad, E.; Gopidas, K. R. J. Am. Chem. Soc. 2001, 123, 1159. (d) Schenning, A. P. H. J.; van Herrikhuyzen, J.; Jonkheijm, P.; Chen, Z.; Wuerthner, F.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 10252.
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33. For recent examples, see: (a) Arkin, M. R.; Stemp, E. D. A.; Turro, C.; Turro, N. J.; Barton, J. K. J. Am. Chem. Soc. 1996, 118, 2267. (b) Kropf, M.; Joselevich, E.; Dürr, H.; Willner, I. J. Am. Chem. Soc. 1996, 118, 655. (c) Avid, E.; Born, R.; Kaganer, E.; Joselevich, E.; DÜrr, H.; Willner, I. J. Am. Chem. Soc. 1997, 119, 7778. (d) Kang, Y. K.; Rubtsov, I. V.; Iovine, P. M.; Chen, J.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 8275.
34. For recent examples, see: (a) Arkin, M. R.; Stemp, E. D. A.; Turro, C.; Turro, N. J.; Barton, J. K. J. Am. Chem. Soc. 1996, 118, 2267. (b) Kropf, M.; Joselevich, E.; Dürr, H.; Willner, I. J. Am. Chem. Soc. 1996, 118, 655. (c) Avid, E.; Born, R.; Kaganer, E.; Joselevich, E.; DÜrr, H.; Willner, I. J. Am. Chem. Soc. 1997, 119, 7778. (d) Kang, Y. K.; Rubtsov, I. V.; Iovine, P. M.; Chen, J.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 8275.
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36. For recent examples, see: (a) Bodenant, B.; Pages, F. J. Am. Chem. Soc. 1998, 120, 7511. (b) Willner, I.; Kaganer, E.; Joselevich, E.; Dürr, H.; David, E.; Günter, M. J.; Johnston, M. R. Coord. Chem. Rev. 1998, 171, 261. (c) Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem., Int. Ed. 1998, 37, 354. (d) Kropf, M.; van Loyen, D.; Schwarz, O.; Dürr, H. J. Phys. Chem. A 1998, 102, 5499. (e) König, B.; Pelka, M.; Zieg, H.; Ritter, T.; Bouas-Laurent, H.; Bonneau, R.; Desvergne, J.-P. J. Am. Chem. Soc. 1999, 121, 1681. (f) Xie, P.-H.; Zhang, L.-Q.; Hou, Y.-J.; Zhang, B.-W.; Cao, Y.; Wu, F.; Tian, W.-J.; Shen, J.-C. Chin. J. Chem. 2000, 78, 152. (g) Li, J.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.-J.; Tung, C.-H. Chin. J. Chem. 2001, 79, 960. (h) Bruseghini, I.; Fabbrizzi, L. Licchelli, M.; Taglietti, A. Chem. Commun. 2002, 1348. (i) Kercher, M.; Koenig, B.; Zieg, H.; De Cola, L. J. Am. Chem. Soc. 2002, 124, 11541.
37. For recent examples, see: (a) Bodenant, B.; Pages, F. J. Am. Chem. Soc. 1998, 120, 7511. (b) Willner, I.; Kaganer, E.; Joselevich, E.; Dürr, H.; David, E.; Günter, M. J.; Johnston, M. R. Coord. Chem. Rev. 1998, 171, 261. (c) Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem., Int. Ed. 1998, 37, 354. (d) Kropf, M.; van Loyen, D.; Schwarz, O.; Dürr, H. J. Phys. Chem. A 1998, 102, 5499. (e) König, B.; Pelka, M.; Zieg, H.; Ritter, T.; Bouas-Laurent, H.; Bonneau, R.; Desvergne, J.-P. J. Am. Chem. Soc. 1999, 121, 1681. (f) Xie, P.-H.; Zhang, L.-Q.; Hou, Y.-J.; Zhang, B.-W.; Cao, Y.; Wu, F.; Tian, W.-J.; Shen, J.-C. Chin. J. Chem. 2000, 78, 152. (g) Li, J.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.-J.; Tung, C.-H. Chin. J. Chem. 2001, 79, 960. (h) Bruseghini, I.; Fabbrizzi, L. Licchelli, M.; Taglietti, A. Chem. Commun. 2002, 1348. (i) Kercher, M.; Koenig, B.; Zieg, H.; De Cola, L. J. Am. Chem. Soc. 2002, 124, 11541.
38. For recent examples, see: (a) Bodenant, B.; Pages, F. J. Am. Chem. Soc. 1998, 120, 7511. (b) Willner, I.; Kaganer, E.; Joselevich, E.; Dürr, H.; David, E.; Günter, M. J.; Johnston, M. R. Coord. Chem. Rev. 1998, 171, 261. (c) Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem., Int. Ed. 1998, 37, 354. (d) Kropf, M.; van Loyen, D.; Schwarz, O.; Dürr, H. J. Phys. Chem. A 1998, 102, 5499. (e) König, B.; Pelka, M.; Zieg, H.; Ritter, T.; Bouas-Laurent, H.; Bonneau, R.; Desvergne, J.-P. J. Am. Chem. Soc. 1999, 121, 1681. (f) Xie, P.-H.; Zhang, L.-Q.; Hou, Y.-J.; Zhang, B.-W.; Cao, Y.; Wu, F.; Tian, W.-J.; Shen, J.-C. Chin. J. Chem. 2000, 78, 152. (g) Li, J.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.-J.; Tung, C.-H. Chin. J. Chem. 2001, 79, 960. (h) Bruseghini, I.; Fabbrizzi, L. Licchelli, M.; Taglietti, A. Chem. Commun. 2002, 1348. (i) Kercher, M.; Koenig, B.; Zieg, H.; De Cola, L. J. Am. Chem. Soc. 2002, 124, 11541.
39. For recent examples, see: (a) Bodenant, B.; Pages, F. J. Am. Chem. Soc. 1998, 120, 7511. (b) Willner, I.; Kaganer, E.; Joselevich, E.; Dürr, H.; David, E.; Günter, M. J.; Johnston, M. R. Coord. Chem. Rev. 1998, 171, 261. (c) Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem., Int. Ed. 1998, 37, 354. (d) Kropf, M.; van Loyen, D.; Schwarz, O.; Dürr, H. J. Phys. Chem. A 1998, 102, 5499. (e) König, B.; Pelka, M.; Zieg, H.; Ritter, T.; Bouas-Laurent, H.; Bonneau, R.; Desvergne, J.-P. J. Am. Chem. Soc. 1999, 121, 1681. (f) Xie, P.-H.; Zhang, L.-Q.; Hou, Y.-J.; Zhang, B.-W.; Cao, Y.; Wu, F.; Tian, W.-J.; Shen, J.-C. Chin. J. Chem. 2000, 78, 152. (g) Li, J.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.-J.; Tung, C.-H. Chin. J. Chem. 2001, 79, 960. (h) Bruseghini, I.; Fabbrizzi, L. Licchelli, M.; Taglietti, A. Chem. Commun. 2002, 1348. (i) Kercher, M.; Koenig, B.; Zieg, H.; De Cola, L. J. Am. Chem. Soc. 2002, 124, 11541.
40. For recent examples, see: (a) Bodenant, B.; Pages, F. J. Am. Chem. Soc. 1998, 120, 7511. (b) Willner, I.; Kaganer, E.; Joselevich, E.; Dürr, H.; David, E.; Günter, M. J.; Johnston, M. R. Coord. Chem. Rev. 1998, 171, 261. (c) Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem., Int. Ed. 1998, 37, 354. (d) Kropf, M.; van Loyen, D.; Schwarz, O.; Dürr, H. J. Phys. Chem. A 1998, 102, 5499. (e) König, B.; Pelka, M.; Zieg, H.; Ritter, T.; Bouas-Laurent, H.; Bonneau, R.; Desvergne, J.-P. J. Am. Chem. Soc. 1999, 121, 1681. (f) Xie, P.-H.; Zhang, L.-Q.; Hou, Y.-J.; Zhang, B.-W.; Cao, Y.; Wu, F.; Tian, W.-J.; Shen, J.-C. Chin. J. Chem. 2000, 78, 152. (g) Li, J.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.-J.; Tung, C.-H. Chin. J. Chem. 2001, 79, 960. (h) Bruseghini, I.; Fabbrizzi, L. Licchelli, M.; Taglietti, A. Chem. Commun. 2002, 1348. (i) Kercher, M.; Koenig, B.; Zieg, H.; De Cola, L. J. Am. Chem. Soc. 2002, 124, 11541.
41. For recent examples, see: (a) Bodenant, B.; Pages, F. J. Am. Chem. Soc. 1998, 120, 7511. (b) Willner, I.; Kaganer, E.; Joselevich, E.; Dürr, H.; David, E.; Günter, M. J.; Johnston, M. R. Coord. Chem. Rev. 1998, 171, 261. (c) Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem., Int. Ed. 1998, 37, 354. (d) Kropf, M.; van Loyen, D.; Schwarz, O.; Dürr, H. J. Phys. Chem. A 1998, 102, 5499. (e) König, B.; Pelka, M.; Zieg, H.; Ritter, T.; Bouas-Laurent, H.; Bonneau, R.; Desvergne, J.-P. J. Am. Chem. Soc. 1999, 121, 1681. (f) Xie, P.-H.; Zhang, L.-Q.; Hou, Y.-J.; Zhang, B.-W.; Cao, Y.; Wu, F.; Tian, W.-J.; Shen, J.-C. Chin. J. Chem. 2000, 78, 152. (g) Li, J.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.-J.; Tung, C.-H. Chin. J. Chem. 2001, 79, 960. (h) Bruseghini, I.; Fabbrizzi, L. Licchelli, M.; Taglietti, A. Chem. Commun. 2002, 1348. (i) Kercher, M.; Koenig, B.; Zieg, H.; De Cola, L. J. Am. Chem. Soc. 2002, 124, 11541.
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84. On the basis of a theoretical study, we concluded that NBCD should adopt a rim-covering conformation in aqueous solution. (Feng, Y.; Zhang, H.-M.; Liu, L.; Wang, Y.-H.; Liang, Z.-X.; Guo, Q.-X. Chin. Chem. Lett. 2001, 12, 637.) The p-nitrobenzoyl moiety cannot enter the CD cavity because of the geometry of the ester bond. Therefore, the CD cavity of NBCD is open for the guest compound in the solution.
85. For more details about the mechanism and application of the SternVolmer equation, please see: (a) Zeng, H. P. Chin. Chem. Lett. 2002, 13, 1231. (b) Zeng, H.-P. Chin. J. Chem. 2002, 20, 1546. (c) Zeng, H. P. Chin. J. Chem. 2002, 20, 1025. (d) Zeng, H. P. Chin. J. Chem. 2002, 20, 1007. (e) Zeng, H. P. Acta Chim. Sin. 2002, 60, 1543. (f) Zeng, H.-P. Chin. J. Org. Chem. 2003, 25, 447.
86. For more details about the mechanism and application of the SternVolmer equation, please see: (a) Zeng, H. P. Chin. Chem. Lett. 2002, 13, 1231. (b) Zeng, H.-P. Chin. J. Chem. 2002, 20, 1546. (c) Zeng, H. P. Chin. J. Chem. 2002, 20, 1025. (d) Zeng, H. P. Chin. J. Chem. 2002, 20, 1007. (e) Zeng, H. P. Acta Chim. Sin. 2002, 60, 1543. (f) Zeng, H.-P. Chin. J. Org. Chem. 2003, 25, 447.
87. For more details about the mechanism and application of the SternVolmer equation, please see: (a) Zeng, H. P. Chin. Chem. Lett. 2002, 13, 1231. (b) Zeng, H.-P. Chin. J. Chem. 2002, 20, 1546. (c) Zeng, H. P. Chin. J. Chem. 2002, 20, 1025. (d) Zeng, H. P. Chin. J. Chem. 2002, 20, 1007. (e) Zeng, H. P. Acta Chim. Sin. 2002, 60, 1543. (f) Zeng, H.-P. Chin. J. Org. Chem. 2003, 25, 447.
88. For more details about the mechanism and application of the SternVolmer equation, please see: (a) Zeng, H. P. Chin. Chem. Lett. 2002, 13, 1231. (b) Zeng, H.-P. Chin. J. Chem. 2002, 20, 1546. (c) Zeng, H. P. Chin. J. Chem. 2002, 20, 1025. (d) Zeng, H. P. Chin. J. Chem. 2002, 20, 1007. (e) Zeng, H. P. Acta Chim. Sin. 2002, 60, 1543. (f) Zeng, H.-P. Chin. J. Org. Chem. 2003, 25, 447.
89. For more details about the mechanism and application of the SternVolmer equation, please see: (a) Zeng, H. P. Chin. Chem. Lett. 2002, 13, 1231. (b) Zeng, H.-P. Chin. J. Chem. 2002, 20, 1546. (c) Zeng, H. P. Chin. J. Chem. 2002, 20, 1025. (d) Zeng, H. P. Chin. J. Chem. 2002, 20, 1007. (e) Zeng, H. P. Acta Chim. Sin. 2002, 60, 1543. (f) Zeng, H.-P. Chin. J. Org. Chem. 2003, 25, 447.
90. For more details about the mechanism and application of the SternVolmer equation, please see: (a) Zeng, H. P. Chin. Chem. Lett. 2002, 13, 1231. (b) Zeng, H.-P. Chin. J. Chem. 2002, 20, 1546. (c) Zeng, H. P. Chin. J. Chem. 2002, 20, 1025. (d) Zeng, H. P. Chin. J. Chem. 2002, 20, 1007. (e) Zeng, H. P. Acta Chim. Sin. 2002, 60, 1543. (f) Zeng, H.-P. Chin. J. Org. Chem. 2003, 25, 447.
91. -2 μM. This means that less than 1% of ZnTPPMO is included in the NBCD cavity. As a result, the quenching of ZnTPPMO fluorescence by NBCD should predominantly be bimolecular dynamic quenching.
92. Rudiger, V.; Eliseev, A.; Simova, S.; Schneider, H.-J.; Blandamer, M. J. ; Cullis, P. M.; Meyer, A. J. J. Chem. Soc., Perkin Trans. 2 1996, 2119.
93. 4A. This decrease clearly is caused by the dynamic quenching between uncomplexed ZnPC4A and NBCD.
94. i) terms. The internal term should also be roughly the same for different n. Therefore, the difference in the observed electron transfer rate should rely on the solvent reorganization energy, which is dependent on the donor-acceptor distance and donor-acceptor orientation.