Modulation of excited-state proton transfer of 2-(2'-hydroxyphenyl) benzimidazole in a macrocyclic cucurbit[7]uril host cavity: Dual emission behavior and pKa shift

Chemistry - A European Journal

Volumn 15, Issue 45, 2009, Pages 12362-12370

  Shaikh, Mhejabeen ^a   Dutta Choudhury, Sharmistha D ^a   Mohanty, Jyotirmayee ^a   Bhasikuttan, Achikanath C ^a   Nau, Werner M ^b   Pal, Haridas ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

^b JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

Cucurbituril; Fluorescence; Host guest systems; Macrocycles; Proton transfer

Indexed keywords

AQUEOUS SOLUTIONS; BENZIMIDAZOLES; BINDING CONSTANT; BLUE EMISSION BANDS; CATIONIC FORMS; CUCURBIT[7]URIL; CUCURBITURIL; CUCURBITURILS; DEPROTONATION PROCESS; DUAL EMISSIONS; EXCITED-STATE PROTON TRANSFER; GROUND STATE ABSORPTION; HOST-GUEST SYSTEM; INCLUSION COMPLEX; INTRAMOLECULAR PROTON-TRANSFER; MACROCYCLES; MACROCYCLICS; PH-DEPENDENT; PHOTOPHYSICAL PROPERTIES; STATE MODELS; TIME-RESOLVED FLUORESCENCE MEASUREMENTS;

DYES; EQUILIBRIUM CONSTANTS; EXCITED STATES; FLUORESCENCE; OPTICAL DEVICES; POSITIVE IONS;

PROTON TRANSFER;

EID: 70849134918     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900390     Document Type: Article

References (39)

1. M. Mosquera, J. C. Penedo, M. C. R. Rodriguez, F. RodriguezPrieto, J. Phys. Chem. 1996, 100, 5398-5407.
2. R. de Vivie-Riedle, V. D. Waele, L. Kurtz, E. Riedle, J. Phys. Chem. A 2003, 107, 10591-10599.
3. C. Hsieh, Y. Cheng, C. Hsu, K. Chen, P. Chou, J. Phys. Chem. A 2008, 112, 8323-8332.
4. S. Lochbrunner, A. J. Wurzer, E. Riedle, J. Phys. Chem. A 2003, 107, 10580-10590.
5. H. Xu, Z.-F. Xu, Z.-Y. Yue, P.-F. Yan, B. Wang, L.-W. Jia, G.-M. Li, W.-B. Sun, J.-W. Zhang, J. Phys. Chem. C. 2008, 112, 15517-15525.
6. S. Ríos Vázquez, M. C. R. Rodriguez, M. Mosquera, F. Rodriguez-Prieto, J. Phys. Chem. A 2007, 111, 1814-1826.
7. J. Catalan, F. Fabero, R. M. Claramunt, M. D. S. Maria, M. C. Foces-Foces, F. H. Cano, M. Martinez-Ripoll, J. Elguero, R. Sastre, J. Am. Chem. Soc. 1992, 114, 5039-5048.
8. J. Catalan, F. Fabero, M.S. Guijarro, R. M. Claramunt, M. D. S. Maria, M. C. Foces-Foces, F. H. Cano, J. Elguero, R. Sastre, J. Am. Chem. Soc. 1990, 112, 747-759.
9. F. Rodríguez-Prieto, J. C. Penedo, M. Mosquera, J. Chem. Soc. Faraday Trans 1998, 94, 2775-2782.
10. H. K. Sinha, S. K. Dogra, J. Photochem. 1987, 36, 149-161.
11. K. Das, N. Sarkar, A. K. Ghosh, D. Majumdar, D. N. Nath, K. Bhattacharyya, J. Phys. Chem. 1994, 98, 9126-9132.
12. J. W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, K. Kim, Acc. Chem. Res. 2003, 36, 621-630.
13. J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, Angew. Chem. 2005, 117, 4922-4949;
14. Angew. Chem. Int. Ed. 2005, 44, 48444870.
15. H.-J. Kim, W. S. Jeon, Y. H. Ko, K. Kim, Proc. Natl. Acad. Sci. USA 2002, 99, 5007-5011.
16. S. Sun, R. Zhang, S. Andersson, J. Pan, D. Zou, B. Åkermark, L. Sun, J. Phys. Chem. B 2007, 111, 13357-13363.
17. J. Mohanty, A. C. Bhasikuttan, S. Dutta Choudhury, H. Pal, J. Phys. Chem. B 2008, 112, 10782-10785.
18. N. Saleh, A. L. Koner, W. M. Nau, Angew. Chem. 2008, 120, 5478-5481;
19. Angew. Chem. Int. Ed. 2008, 47, 5398-5401.
20. P. Montes-Navajas, A. Corma, H. Garcia, J. Mol. Catal. A 2008, 279, 165-169.
21. L. Liu, N. Zhao, O. A. Scherman, Chem. Commun. 2008, 1070-1072.
22. J. Mohanty, W. M. Nau, Angew. Chem. 2005, 117, 3816-3820;
23. Angew. Chem. Int. Ed. 2005, 44, 3750-3754.
24. A. C. Bhasikuttan, J. Mohanty, W. M. Nau, H. Pal, Angew. Chem. 2007, 119, 4198-4200;
25. Angew. Chem. Int. Ed. 2007, 46, 4120-4122.
26. W. M. Nau, J. Mohanty, Int. J. Photoenergy 2005, 7, 133-141.
27. J. Mohanty, A. C. Bhasikuttan, W. M. Nau, H. Pal, J. Phys. Chem. B 2006, 110, 5132-5138.
28. R. Wang, D. H. Macartney, Org. Biomol. Chem. 2008, 6, 1955-1960.
29. M. D. Pluth, R. G. Bergman, K. N. Raymond, Science 2007, 316, 85-88.
30. R. Wang, L. Yuan, D.H. Macartney, Chem. Commun. 2005, 5867-5869.
31. M. Shaikh, J. Mohanty, A. C. Bhasikuttan, V. D. Uzunova, W. M. Nau, H. Pal, Chem. Commun. 2008, 3681-3683.
32. A. M. M. Rawashdeh, A. Thangavel, C. Sotiriou-Leventis, N. Leventis, Org. Lett. 2008, 10, 1131-1134.
33. H. K. Sinha, S. K. Dogra, Chem. Phys. 1986, 102, 337-347.
34. K. K. Rohatgi-Mukherjee, Fundamentals of Photochemistry, New Age International Limited, New Delhi, 1986.
35. M. Shaikh, J. Mohanty, P. K. Singh, W. M. Nau, H. Pal, Photochem. Photobiol. Sci. 2008, 7, 408-414.
36. H. Bakirci, A. L. Koner, T. Schwarzlose, Chem. Eur. J. 2006, 12, 4799-4807.
37. E. L. Roberts, J. Dey, I. M. Warner, J. Phys. Chem. 1996, 100, 19681-19686.
38. C. Marquez, F. Huang, W. M. Nau, IEEF. Trans. Nanobiosci. 2004, 3, 39-45.
39. Gaussian 92, Revision E.l, M.J. Frisch, G.W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1992.