Temperature effect on dual fluorescence of 2-(2′-hydroxyphenyl) benzimidazole and its nitrogen substituted analogues

Journal of Physical Chemistry B

Volumn 117, Issue 45, 2013, Pages 14079-14088

  Chipem, Francis A S ^a   Krishnamoorthy, Govindarajan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; ETHYLENE GLYCOL; FLUORESCENCE; HYDROGEN BONDS; NITROGEN; PYRIDINE;

DENSITY FUNCTIONALS; DUAL FLUORESCENCE; EFFECTS OF TEMPERATURE; NONRADIATIVE DECAYS; POPULATION RATIO; THEORETICAL CALCULATIONS; TIME-RESOLVED EMISSIONS; VAN'T HOFF EQUATION;

TEMPERATURE;

2 (2' HYDROXYPHENYL) 3H IMIDAZO(4,5 B)PYRIDINE; 2-(2'-HYDROXYPHENYL)-3H-IMIDAZO(4,5-B)PYRIDINE; BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; ETHYLENE GLYCOL; FLUORESCENT DYE; IMIDAZOLE DERIVATIVE; METHANOL; NITROGEN; PYRIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; HYDROGEN BOND; ISOMERISM; TEMPERATURE; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY;

BENZIMIDAZOLES; ETHYLENE GLYCOL; FLUORESCENT DYES; HYDROGEN BONDING; IMIDAZOLES; ISOMERISM; METHANOL; NITROGEN; PYRIDINES; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE; THERMODYNAMICS;

EID: 84887906969     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp405804c     Document Type: Article

References (55)

1. Efremov, R. G.; Baradaran, R.; Sazanov, L. A. The Architecture of Respiratory Complex I Nature 2010, 465, 441-445
2. Ohnishi, T. Structural Biology: Piston Drives a Proton Pump Nature 2010, 465, 428-429
3. Formosinho, S. J.; Arnaut, L. G. Excited-State Proton Transfer Reactions II. Intramolecular Reactions J. Photochem. Photobiol., A 1993, 75, 21-48
4. Kwon, J. E.; Park, S. Y. Advanced Organic Optoelectronic Materials: Harnessing Excited-State Intramolecular Proton Transfer (ESIPT) Process Adv. Mater. 2011, 23, 3615-3642
5. Chipem, F. A. S.; Mishra, A.; Krishnamoorthy, G. The Role of Hydrogen Bonding in Excited State Intramolecular Charge Transfer Phys. Chem. Chem. Phys. 2012, 14, 8775-8790
6. 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
7. Barbara, P. F.; Walsh, P. K. Picosecond Kinetic and Vibrationally Resolved Spectroscopic Studies of Intramolecular Excited-State Hydrogen Atom Transfer J. Phys. Chem. 1989, 93, 29-34
8. Irie, M. Diarylethenes for Memories and Switches Chem. Rev. 2000, 100, 1685-1716
9. Chou, P.-T.; Huang, C.-H.; Pu, S.-C.; Cheng, Y.-M.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Tuning Excited-State Charge/Proton Transfer Coupled Reaction via the Dipolar Functionality J. Phys. Chem. A 2004, 108, 6452-6454
10. Celej, M. S.; Caarls, W.; Demchenko, A. P.; Jovin, T. M. A Triple-Emission Fluorescent Probe Reveals Distinctive Amyloid Fibrillar Polymorphism of Wild-Type α-Synuclein and Its Familial Parkinson's Disease Mutants Biochemistry 2009, 48, 7465-7472
11. Chen, W.-H.; Xing, Y.; Pang, Y. A Highly Selective Pyrophosphate Sensor Based on ESIPT Turn-On in Water Org. Lett. 2011, 13, 1362-1365
12. Zhang, G.; Wang, H.; Yu, Y.; Xiong, F.; Tang, G.; Chen, W. Optical Switching of 2-(2′-Hydroxyphenyl)benzoxazole in Different Solvents Appl. Phys. B: Lasers and Opt. 2003, 76, 677-681
13. Paterson, M. J.; Robb, M. A.; Blancafort, L.; DeBellis, A. D. Mechanism of an Exceptional Class of Photostabilizers: A Seam of Conical Intersection Parallel to Excited State Intramolecular Proton Transfer (ESIPT) in o -Hydroxyphenyl-(1,3,5)-triazine J. Phys. Chem. A 2005, 109, 7527-7537
14. Tang, K.-C.; Chang, M.-J.; Lin, T.-Y.; Pan, H.-A.; Fang, T.-C.; Chen, K.-Y.; Hung, W.-Y.; Hsu, Y.-H.; Chou, P.-T. Fine Tuning the Energetics of Excited-State Intramolecular Proton Transfer (ESIPT): White Light Generation in A Single ESIPT System J. Am. Chem. Soc. 2011, 133, 17738-17745
15. Lim, S.-J.; Seo, J.; Park, S. Y. Photochromic Switching of Excited-State Intramolecular Proton-Transfer (ESIPT) Fluorescence: A Unique Route to High-Contrast Memory Switching and Nondestructive Readout J. Am. Chem. Soc. 2006, 128, 14542-14547
16. 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
17. 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
18. Vázquez, S. R.; Rodríguez, M. C. R.; Rodríguez- Prieto, M. M. 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
19. Sinha, H. K.; Dogra, S. K. Ground and Excited State Prototropic Reactions in 2-(o -Hydroxyphenyl)benzimidazole Chem. Phys. 1986, 102, 337-347
20. 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
21. del Valle, J. C.; Claramunt, R. M.; Catalán, J. Fluorescence Spectroscopy and Amplified Spontaneous Emission (ASE) of Phenylimidazoles: Predicted Vibronic Coupling Along the Excited-State Intramolecular Proton Transfer in 2-(2′-Hydroxyphenyl)imidazoles J. Phys. Chem. A 2008, 112, 5555-5565
22. Henary, M. M.; Wu, Y.; Cody, J.; Sumalekshmy, S.; Li, J.; Mandal, S.; Fahrni, C. J. Excited-State Intramolecular Proton Transfer in 2-(2′-Arylsulfonamidophenyl)benzimidazole Derivatives: The Effect of Donor and Acceptor Substituents J. Org. Chem. 2007, 72, 4784-4797
23. Cheng, Y.-M.; Pu, S.-C.; Hsu, C.-J.; Lai, C.-H.; Chou, P.-T. Femtosecond Dynamics on 2-(2′-Hydroxy-4′-diethylaminophenyl)benzothiazole: Solvent Polarity in the Excited-State Proton Transfer ChemPhysChem 2006, 7, 1372-1381
24. Kim, Y. H.; Roh, S.-G.; Jung, S.-D.; Chung, M.-A.; Kim, H. K.; Cho, D. W. Excited-State Intramolecular Proton Transfer on 2-(2′-Hydroxy-4′-R- phenyl)benzothiazole Nanoparticles and Fluorescence Wavelength Depending on Substituent and Temperature Photochem. Photobiol. Sci. 2010, 9, 722-729
25. Mordziński, A.; Grabowska, A. Intramolecular Proton Transfer in Excited Benzoxazoles Chem. Phys. Lett. 1982, 90, 122-127
26. Barbara, P. F.; Brus, L. E.; Rentzepis, P. M. Intramolecular Proton Transfer and Excited-State Relaxation in 2-(2-Hydroxyphenyl)benzothiazole J. Am. Chem. Soc. 1980, 102, 5631-5635
27. Al-Soufi, W.; Grellmann, K. H.; Nickel, B. Triplet State Formation and cis → trans Isomerization in the Excited Singlet State of the Keto Tautomer of 2-(2′-Hydroxyphenyl)benzothiazole Chem. Phys. Lett. 1990, 174, 609-616
28. Brewer, W. E.; Martinez, M. L.; Chou, P.-T. Mechanism of the Ground-State Reverse Proton Transfer of 2-(2-Hydroxyphenyl)benzothiazole J. Phys. Chem. 1990, 94, 1915-1918
29. Stephan, J. S.; Grellmann, K. H. Photoisomerization of 2-(2′-Hydroxyphenyl)benzoxazole. Formation and Decay of the Trans-Keto Tautomer in Dry and in Water-Containing 3-Methylpentane J. Phys. Chem. 1995, 99, 10066-10068
30. Nagaoka, S.; Itoh, A.; Mukai, K.; Nagashima, U. Investigation of Triplet States of 2- (2′-Hydroxyphenyl)benzothiazole and 2-(2′- Hydroxypbenyl)benzoxazole by Transient Absorption Spectroscopy and ab Initio Calculations J. Phys. Chem. 1993, 97, 11385-11392
31. 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, 12063-12703
32. Chipem, F. A. S.; Dash, N.; 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, 104308-1-104308-9
33. 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
34. 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
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. Rettig, W. Charge Separation in Excited States of Decoupled Systems-TICT Compounds and Implications Regarding the Development of New Laser Dyes and the Primary Process of Vision and Photosynthesis Angew. Chem., Int. Ed. Engl. 1986, 25, 971-988
39. Kawski, A.; Kukliński, B.; Bojarski, P. Temperature Influence on Dual Fluorescence of 4-(Dimethylamino)benzaldehyde in 1,2-Dichloroethane and Ethyl Acetate Chem. Phys. Lett. 2008, 455, 52-54
40. Wohlfarth, C. Permittivity (Dielectric Constant) of Liquids. In CRC Handbook of Chemistry and Physics, 91 st ed.; Haynes, W. M., Ed.; CRC Press, Taylor & Francis Group, New York, 2010; Section 6, pp 186-207.
41. Refractive Indices of Pure Liquids and Binary Liquids Mixtures (Supplement to III/38); Book Series: Landolt-Börnstein-Group III Condensed Matter; Springer: Berlin, Heidelberg, 2008; Vol. 47, DOI: 10.1007/978-3-540- 75291-2.
42. Miertuš, S.; Scrocco, E.; Tomasi, J. Electrostatic Interaction of A Solute With A Continuum. A Direct Utilization of Ab Initio Molecular Potentials for the Prevision of Solvent Effects Chem. Phys. 1981, 55, 117-129
43. Cancès, E.; Mennucci, B.; Tomasi, J. A New Integral Equation Formalism for the Polarizable Continuum Model: Theoretical Background and Applications to Isotropic and Anisotropic Dielectrics J. Chem. Phys. 1997, 107, 3032-3041
44. Hohenberg, P.; Kohn, W. Inhomogeneous Electron Gas Phys. Rev. B 1964, 136, 864-871
45. Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects Phys. Rev. A 1965, 140, 1133-1138
46. Becke, A. D. Density Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
47. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula Into A Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
48. 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.; Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
49. 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
50. Dupradeau, F. Y.; Case, D. A.; Yu, C. Z.; Jimenez, R.; Romesberg, F. E. Differential Solvation and Tautomer Stability of a Model Base Pair within the Minor and Major Grooves of DNA J. Am. Chem. Soc. 2005, 127, 15612-15617
51. 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
52. Kim, Y.; Yoon, M.; Kim, D. Excited-State Intramolecular Proton Transfer Coupled-Charge Transfer of p-N, N -Dimethylaminosalicylic Acid in Aqueous β-Cyclodextrin Solutions J. Photochem. Photobiol., A 2001, 138, 167-175
53. James, D. R.; Ware, W. R. A Fallacy in the Interpretation of Fluorescence Decay Parameters Chem. Phys. Lett. 1985, 120, 455-459
54. Santra, S.; Dogra, S. K. Excited-State Intramolecular Proton Transfer in 2-(2′-Aminophenyl)benzimidazole Chem. Phys. 1998, 226, 285-296
55. Krishnamoorthy, G.; Dogra, S. K. Dual Fluorescence of 2-(4′- N, N -Dimethylaminophenyl)pyrido[3,4- d ]imidazole: Effect of Solvents Spectrochim. Acta, Part A 1999, 55, 2647-2658 Technology