Enhancing excited state intramolecular proton transfer in 2-(2′-hydroxyphenyl)benzimidazole and its nitrogen-substituted analogues by β-cyclodextrin: The effect of nitrogen substitution

Journal of Physical Chemistry A

Volumn 117, Issue 20, 2013, Pages 4084-4095

  Chipem, Francis A S ^a   Behera, Santosh Kumar ^a   Krishnamoorthy, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLES; BINDING CONSTANT; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; GUEST MOLECULES; INTRAMOLECULAR CHARGE TRANSFERS; MONOANIONIC FORMS; NMR EXPERIMENTS; NONRADIATIVE DECAYS;

EXCITED STATES; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSFER; PYRIDINE; STOICHIOMETRY;

NITROGEN;

BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; DIMETHYL(3,3,3 TRIFLUOROPROPYL)SILYLDIETHYLAMINE; DIMETHYL(3,3,3-TRIFLUOROPROPYL)SILYLDIETHYLAMINE; ETHYLAMINE; NITROGEN; PROTON; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMISTRY; QUANTUM THEORY;

BETA-CYCLODEXTRINS; ETHYLAMINES; NITROGEN; PROTONS; QUANTUM THEORY; TRIMETHYLSILYL COMPOUNDS;

EID: 84878207513     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp311438s     Document Type: Article

References (80)

1. Rekharsky, M. V.; Inoue, Y. Complexation Thermodynamics of Cyclodextrins Chem. Rev. 1998, 98, 1875-1918
2. Villalonga, R.; Cao, R.; Fragoso, A. Supramolecular Chemistry of Cyclodextrins in Enzyme Technology Chem. Rev. 2007, 107, 3088-3116
3. Ukeama, K.; Hirayama, F.; Irie, T. Cyclodextrin Drug Carrier Systems Chem. Rev. 1998, 98, 2045-2076
4. Breslow, R.; Dong, S. D. Biomimetic Reactions Catalyzed by Cyclodextrins and Their Derivatives Chem. Rev. 1998, 98, 1997-2011
5. Harada, A. Cyclodextrin-Based Molecular Machines Acc. Chem. Res. 2001, 34, 456-464
6. Hashimoto, S.; Thomas, J. K. Fluorescence Study of Pyrene and Naphthalene in Cyclodextrin-Amphiphile Complex Systems J. Am. Chem. Soc. 1985, 107, 4655-4662
7. Blyshak, L. A.; Rossi, T. M.; Patonay, G.; Warner, I. M. Cyclodextrin-Modified Solvent Extraction for Polynuclear Aromatic Hydrocarbons Anal. Chem. 1988, 60, 2127-2131
8. Iglesias, E. Inclusion Complexation of Novocaine by in Aqueous Solutions J. Org. Chem. 2006, 71, 4383-4392
9. Banerjee, A.; Basu, K.; Sengupta, P. K. Effect of β-Cyclodextrin Nanocavity Confinement on the Photophysics of Robinetin J. Photochem. Photobiol., B 2007, 89, 88-97
10. Sanz, M.; Organero, J. A.; Douhal, A. Proton and Charge Transfer Reactions Dynamics of a Hydroxyflavone Derivative in a Polar Solvent and in a Cyclodextrin Nanocavity Chem. Phys. 2007, 338, 135-142
11. Dash, N.; Chipem, F. A. S.; Krishnamoorthy, G. Encapsulation of 2-(4′- N, N -Dimethylamino)phenylimidazo[4,5- b ]pyridine in β-Cyclodextrin: Effect on H-Bond-induced Intramolecular Charge Transfer Emission Photochem. Photobiol. Sci. 2009, 8, 1708-1715
12. Das, P.; Chakrabarty, A.; Haldar, B.; Mallick, A.; Chattopadhyay, N. Effect of Cyclodextrin Nanocavity Confinement on the Photophysics of a β-Carboline Analogue: A Spectroscopic Study J. Phys. Chem. B 2007, 111, 7401-7408
13. Matsushita, Y.; Suzuki, T.; Ichimura, T.; Hikida, T. Cavity Size Effect on the Excited State Dynamics of Methyl 4-(Dimethylamino)benzoate-Cyclodextrin Complexes J. Phys. Chem. A 2004, 108, 7490-7496
14. Ralkshit, S.; Vasudevan, S. Resonance Energy Transfer from β-Cyclodextrin-Capped ZnO:MgO Nanocrystals to Included Nile Red Guest Molecules in Aqueous Media ACS Nano 2008, 2, 1473-1479
15. Faiz, J. A.; Kyllonen, L. E. P.; Contreras-Carballada, P.; Williams, R. M.; De Cola, L.; Pikramenou, Z. Photoinduced Energy Transfer Across Non-Covalent Bonds in the Nanoscale: Cyclodextrin Hosts with Enhanced Luminescent Properties for Guest Communication Dalton Trans. 2009, 3980-3987
16. Douhal, A. Ultrafast Guest Dynamics in Cyclodextrin Nanocavities Chem. Rev. 2004, 104, 1955-1976
17. Martín, C.; Gil, M.; Cohen, B.; Douhal, A. Ultrafast Photodynamics of Drugs in Nanocavities: Cyclodextrins and Human Serum Albumin Protein Langmuir 2012, 28, 6746-6759
18. D'Souza, R. N.; Pischel, U.; Nau, W. M. Fluorescent Dyes and Their Supramolecular Host/Guest Complexes with Macrocycles in Aqueous Solution Chem. Rev. 2011, 111, 7941-7980
19. Wagner, B. D. Hydrogen Bonding of Excited States in Supramolecular Host-Guest Inclusion Complexes Phys. Chem. Chem. Phys. 2012, 14, 8825-8835
20. Roberts, E. L.; Chou, P. T.; Alexander, T. A.; Agbaris, R. A.; Warner, I. M. Effects of Organized Media on the Excited-State Intramolecular Proton Transfer of 1O-Hydroxybenzo[ h ]quinoline J. Phys. Chem. 1995, 99, 5431-5437
21. Roberts, E. L.; Dey, J.; Warner, I. M. Excited-State Intramolecular Proton Transfer of 2-(2′-Hydroxyphenyl)benzimidazole in Cyclodextrins and Binary Solvent Mixtures J. Phys. Chem. A 1997, 101, 5296-5301
22. Paul, B. K.; Samanta, A.; Guchhait, N. Modulation of Excited-State Intramolecular Proton Transfer Reaction of 1-Hydroxy-2-naphthaldehyde in Different Supramolecular Assemblies Langmuir 2010, 26, 3214-3224
23. Roberts, E. L.; Dey, J.; Warner, I. M. Ground- and Excited-State Structural Orientation of 2-(2′-Hydroxyphenyl)benzazoles in Cyclodextrins J. Phys. Chem. 1996, 100, 19681-19686
24. Sarkar, N.; Das, K.; Das, S.; Datta, A.; Nath, D.; Bhattacharyya, K. Excited-State Intramolecular Proton Transfer of 2-(2′-Hydroxyphenyl) benzimidazole in Micelles J. Phys. Chem. 1995, 99, 17711-17714
25. Sinha, H. K.; Dogra, S. K. Ground and Excited State Prototropic Reactions in 2-(o -Hydroxyphyenyl)benzimidazole Chem. Phys. 1986, 102, 337-347
26. Penedo, J. C.; Mosquera, M.; Rodríguez-Prieto, F. Role of Hydrogen-Bonded Adducts in Excited-State Proton-Transfer Processes J. Phys. Chem. A 2000, 104, 7429-7441
27. Mosquera, M.; Penedo, J. C.; Rodríguez, M. C. R.; Rodríguez-Prieto, F. Photoinduced Inter- and Intramolecular Proton Transfer in Aqueous and Ethanolic Solutions of 2-(2′-Hydroxyphenyl) benzimidazole: Evidence for Tautomeric and Conformational Equilibria in the Ground State J. Phys. Chem. 1996, 100, 5398-5407
28. Douhal, A.; Amat-Guerri, F.; Lillo, M. P.; Acuña, A. U. Proton Transfer Spectroscopy of 2-(2′-Hydroxyphenyl)imidazole and 2-(2′-Hydroxyphenyl)benzimidazole Dyes J. Photochem. Photobiol., A 1994, 78, 127-138
29. Das, K.; Sarkar, N.; Majumdar, D.; Bhattacharyya, K. Excited-State Intramolecular Proton Transfer and Rotamerism of 2-(2′-Hydroxyphenyl) benzimidazole Chem. Phys. Lett. 1992, 198, 443-448
30. Das, K.; Sarkar, N.; Ghosh, A. K.; Majumdar, D.; Nath, D. N.; Bhattacharyya, K. Excited-State Intramolecular Proton Transfer in 2-(2-Hydroxyphenyl)benzimidazole and -benzoxazole: Effect of Rotamerism and Hydrogen Bonding J. Phys. Chem. 1994, 98, 9126-9132
31. Ríos, M. A.; Ríos, M. C. Ab Initio Study of the Hydrogen Bond and Proton Transfer in 2-(2′-Hydroxyphenyl)benzothiazole and 2-(2′-Hydroxyphenyl)benzimidazole J. Phys. Chem. A 1998, 102, 1560-1567
32. Williams, D. L.; Heller, A. Intramolecular Proton Transfer Reactions in Excited Fluorescent Compounds J. Phys. Chem. 1970, 74, 4473-4480
33. Purkayastha, P.; Chattopadhyay, N. Role of Rotamerisation and Excited State Intramolecular Proton Transfer in the Photophysics of 2-(2′- Hydroxyphenyl)benzoxazole, 2-(2′-Hydroxyphenyl)benzimidazole and 2-(2′-Hydroxyphenyl)benzothiazole: A Theoretical Study Phys. Chem. Chem. Phys. 2000, 2, 203-210
34. Vázquez, S. R.; Rodríguez, C. R.; Mosquera, M.; Rodríguez-Prieto, F. Excited-State Intramolecular Proton Transfer in 2-(3′-Hydroxy-2′-pyridyl)benzoxazole. Evidence of Coupled Proton and Charge Transfer in the Excited State of Some o -Hydroxyarylbenzazoles J. Phys. Chem. A 2007, 111, 1814-1826
35. Krishnamoorthy, G.; Dogra, S. K. Excited State Intramolecular Proton Transfer in 2-(2′-Hydroxyphenyl)-3 H -imidazo[4,5- b ]pyridine: Effect of Solvents J. Lumin. 2001, 92, 91-102
36. Krishnamoorthy, G.; Dogra, S. K. Prototropic Reactions of 2-(2′-Hydroxyphenyl)-3 H -imidazo[4,5- b ]pyridine in Aqueous and Organic Solvents J. Lumin. 2001, 92, 103-114
37. Balamurali, M. M.; Dogra, S. K. Excited State Intramolecular Proton Transfer in 2-(2′-Hydroxyphenyl)-1 H -imidazo[4,5- c ]pyridine: Effects of Solvents J. Photochem. Photobiol., A 2002, 154, 81-92
38. Rodríguez-Prieto, F.; Rodríguez, M. C. R.; González, M. M.; Fernández, M. A. R. Ground- and Excited-State Tautomerism in 2-(3′-Hydroxy-2′-pyridyl)benzimidazole J. Phys. Chem. 1994, 98, 8666-8672
39. Brenlla, A.; Veiga, M.; Rodríguez, M. C. R.; Mosquera, M.; Rodríguez-Prieto, F. Fluorescence of Methylated Derivatives of Hydroxyphenylimidazopyridine. Resolution of Strongly Overlapping Spectra and a New ESIPT Dye Showing Very Efficient Radiationless Deactivation Photochem. Photobiol. Sci. 2011, 10, 1622-1636
40. Dogra, S. K. Spectral Characteristics of 2-(2′-Hydroxy-3′- pyridyl)benzimidazole: Effects of Solvents and Acid or Base Concentrations J. Mol. Struct. 2005, 734, 51-60
41. Xiao, D.; Zhang, G.; Wang, H.; Tang, G.; Chen, W. Investigation on Nonlinear Transmission Property of Excited State Proton Transfer Molecule 2-(2′-Hydroxyphenyl)benzoxazole J. Nonlinear Opt. Phys. Mater. 2000, 9, 309-314
42. Hillebrand, S.; Segala, M.; Buckup, T.; Correia, R. R. B.; Horowitz, F.; Stefani, V. First Hyperpolarizability in Proton-Transfer Benzoxazoles: Computer-Aided Design, Synthesis and Study of a New Model Compound Chem. Phys. 2001, 273, 1-10
43. Sakai, K.-I.; Tsuzuki, T.; Itoh, Y.; Ichikawa, M.; Taniguchi, Y. Using Proton-Transfer Laser Dyes for Organic Laser Diodes Appl. Phys. Lett. 2005, 86, 081103
44. Kasha, M. Proton-Transfer Spectroscopy. Perturbation of the Tautomerization Potential J. Chem. Soc., Faraday Trans. 2 1986, 82, 2379-2392
45. Formosinho, S. J.; Arnaut, L. G. Excited-State Proton Transfer Reactions II. Intramolecular Reactions J. Photochem. Photobiol., A 1993, 75, 21-48
46. Waluk, J. Conformational Aspects of Intra- and Intermolecular Excited-State Proton Transfer. In Conformational Analysis of Molecules in Excited States; Waluk, J., Ed.; Wiley-VCH: New York, 2000; Chapter 2, pp 57-112.
47. Zhao, J.; Ji, S.; Chen, Y.; Guo, H.; Yang, P. Excited State Intramolecular Proton Transfer (ESIPT): From Principal Photophysics to the Development of New Chromophores and Applications in Fluorescent Molecular Probes and Luminescent Materials Phys. Chem. Chem. Phys. 2012, 14, 8803-8817
48. Kwon, J. E.; Park, S. Y. Advanced Organic Optoelectronic Materials: Harnessing Excited-State Intramolecular Proton Transfer (ESIPT) Process Adv. Mater. 2011, 23, 3615-3642
49. Hsieh, C.-C.; Jiang, C.-M.; Chou, P.-T. Recent Experimental Advances on Excited-State Intramolecular Proton Coupled Electron Transfer Reaction Acc. Chem. Res. 2010, 43, 1364-1374
50. Sarkar, N.; Datta, A.; Das, S.; Das, K.; Bhattacharyya, K. Dual Emission of 2-(2′-Hydroxyphenyl)-benzimidazole in Reverse Micelle J. Photochem. Photobiol., A 1997, 109, 259-265
51. Das, S. K.; Bansal, A.; Dogra, S. K. Excited State Intramolecular Proton Transfer Reactions in 2-(2-Hydroxyphenyl)benzimidazole in Micellar Solutions Bull. Chem. Soc. Jpn. 1997, 70, 307-313
52. Chattopadhyay, N. Effect of Cyclodextrin Complexation on Excited State Proton Transfer Reactions J. Photochem. Photobiol., A 1991, 58, 31-36
53. Chipem, F. A. S.; Krishnamoorthy, G. Comparative Theoretical Study of Rotamerism and Excited State Intramolecular Proton Transfer of 2-(2′-Hydroxyphenyl)benzimidazole, 2-(2′-Hydroxyphenyl)imidazo[4,5- b ]pyridine, 2-(2′-Hydroxyphenyl)imidazo[4,5- c ]pyridine and 8-(2′-Hydroxyphenyl)purine J. Phys. Chem. A. 2009, 113, 12063-12070
54. Chipem, F. A. S.; Nihar, D.; Krishnamoorthy, G. Role of Nitrogen Substitution in Phenyl Ring on Excited State Intramolecular Proton Transfer and Rotamerism of 2-(2′-Hydroxyphenyl)benzimidazole: A Theoretical Study J. Chem. Phys. 2011, 134, 104308
55. Mosquera, M.; Rodríguez, M. C. R.; Rodríguez-Prieto, F. Competition between Protonation and Deprotonation in the First Excited Singlet State of 2-(3′-Hydroxy-2′-pyridyl)benzimidazole in Acidic Solutions J. Phys. Chem. A 1997, 101, 2766-2772
56. Rodríguez, M. C. R.; Mosquera, M.; Rodríguez-Prieto, F. Ground- and Excited-State Tautomerism in Anionic 2-(6′-Hydroxy-2′- pyridyl)benzimidazole: Role of Solvent and Temperature J. Phys. Chem. A 2001, 105, 10249-10260
57. Chou, P. T.; Cooper, W. C.; Clements, J. H.; Studer, S. L.; Cheng, C. P. A Comparative Study. The Photophysics of 2-Phenylbenzoxazoles and 2-Phenylbenzothiazoles Chem. Phys. Lett. 1993, 216, 300-304
58. LeGourriérec, D.; Kharlanov, V.; Brown, R. G.; Rettig, W. Excited-State Intramolecular Proton Transfer (ESIPT) in 2-(2′- Hydroxyphenyl)-oxazole and -Thiazole J. Photochem. Photobiol., A 2000, 130, 101-111
59. Kharlanov, V. A.; Rettig, W.; Knyazhansky, M. I.; Makaraova, N. Multiple Emission of N-(1-Anthryl)-pyridinium J. Photochem. Photobiol., A 1997, 103, 45-50
60. Chen, W.; Chang, C.-E.; Gilson, M. K. Calculation of Cyclodextrin Binding Affinities: Energy, Entropy, and Implications for Drug Design Biophys. J. 2004, 87, 3035-3049
61. Krishnamoorthy, G.; Dogra, S. K. Twisted Intramolecular Charge Transfer of 2-(4′- N, N -Dimethylaminophenyl)pyrido[3,4- d ]imdazole in Cyclodextrins: Effect of pH J. Phys. Chem. A 2000, 104, 2542-2551
62. Crosby, G. A.; Demas, J. N. Measurement of Photoluminescence Quantum Yields. Review J. Phys. Chem. 1971, 75, 991-1024
63. Jiang, Y.-B. Effect of Cyclodextrin Inclusion Complex Formation on the Twisted Intramolecular Charge Transfer (TICT) of the Included Compound: The p -Dimethylaminobenzoic Acid-β-Cyclodextrin System J. Photochem. Photobiol., A 1995, 88, 109-116
64. Panja, S.; Chowdhury, P.; Chakravorti, S. Modulation of Complexation of 4(1H-Pyrrole-1-yl)benzoic Acid with β-Cyclodextrin in Aqueous and Non-Aqueous Environments Chem. Phys. Lett. 2004, 393, 409-415
65. Critchfield, F. E.; Gibson, J. A., Jr.; Hall, J. L. Dielectric Constant for the Dioxane-Water System from 20 to 35 J. Am. Chem. Soc. 1953, 75, 1991-1992
66. Nigam, S.; Durocher, G. Spectral and Photophysical Studies of Inclusion Complexes of Some Neutral 3 H -Indoles and Their Cations and Anions with β-Cyclodextrin J. Phys. Chem. 1996, 100, 7135-7142
67. Brenlla, A.; Veiga, M.; Lustres, J. L. P.; Rodríguez, M. C. R.; Rodríguez-Prieto, F.; Mosquera, M. Photoinduced Proton and Charge Transfer in 2-(2′-Hydroxyphenyl)imidazo[4,5-b]pyridine J. Phys. Chem. B 2013, 117, 884-896
68. Konoshima, H.; Nagao, S.; Kiyota, I.; Amimoto, K.; Yamamoto, N.; Sekine, M.; Nakata, M.; Furukawa, K.; Sekiya, H. Excited-State Intramolecular Proton Transfer and Charge Transfer in 2-(2′-Hydroxyphenyl)benzimidazole Crystals Studied by Polymorphs-Selected Electronic Spectroscopy Phys. Chem. Chem. Phys. 2012, 14, 16448-16457
69. Douhal, A.; Fiebig, T.; Chachisvilis, M.; Zewail, A. H. Femtochemistry in Nanocavities: Reactions in Cyclodextrins J. Phys. Chem. A 1998, 102, 1657-1660
70. Dash, N.; Chipem, F. A. S.; Swaminathan, R.; Krishnamoorthy, G. Hydrogen Bond Induced Twisted Intramolecular Charge Transfer in 2-(4′- Dimethylaminophenyl)imidazo[4,5- b ]pyridine Chem. Phys. Lett. 2008, 460, 119-124
71. Krishnamoorhy, G. Hydrogen Bonding Effects On Intramolecular Charge Transfer. In Hydrogen Bonding and Transfer in the Excited State; Han, K.-L.; Zhao, G. J., Eds.; John Wiley & Sons Ltd.: New York, 2011; Vol. 1, pp 313-327.
72. Chipem, F. A. S.; Mishra, A.; Krishnamoorthy, G. Role of Hydrogen Bonding in Excited State Intramolecular Charge Transfer Phys. Chem. Chem. Phys. 2012, 14, 8775-8790
73. Benesi, M. L.; Hildebrand, J. H. A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons J. Am. Chem. Soc. 1949, 71, 2703-2707
74. Singh, M. K.; Pal, H.; Koti, A. S. R.; Sapre, A. V. Photophysical Properties and Rotational Relaxation Dynamics of Neutral Red Bound to β-Cyclodextrin J. Phys. Chem. A 2004, 108, 1465-1474
75. Voinov, M. A.; Kirilyuk, I. A.; Smirnov, A. I. Spin-Labeled pH-Sensitive Phospholipids for Interfacial pKa Determination: Synthesis and Characterization in Aqueous and Micellar Solutions J. Phys. Chem. B 2009, 113, 3453-3460
76. Szejtli, J. Cyclodextrins and Their Inclusion Complexes; Akademiai Kiado: Budapest, 1982.
77. Li, S.; Purdy, W. C. Cyciodextrins and Their Applications in Analytical Chemistry Chem. Rev. 1992, 92, 1457-1490
78. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision E.01, Gaussian, Inc.: Wallingford, CT, 2004.
79. Krishnamoorthy, G.; Dogra, S. K. Dual Fluorescence of 2-(4′- N, N -Dimethylaminophenyl)benzimidazole: Effect of β-Cyclodextrin and pH J. Photochem. Photobiol., A 1999, 123, 109-119
80. El-Kemary, M.; Organero, J. A.; Santos, L.; Douhal, A. Effect of Cyclodextrin Nanocavity Confinement on the Photorelaxation of the Cardiotonic Drug Milrinone J. Phys. Chem. B 2006, 110, 14128-14134