Revisit of 4,4′-diaminodiphenyl sulfone photophysics in different solvents

Industrial and Engineering Chemistry Research

Volumn 51, Issue 6, 2012, Pages 2505-2514

  Bhattacharya, Prosenjit ^a   Sahoo, Dibakar ^a   Chakravorti, Sankar ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACCEPTOR MOIETIES; DIAMINODIPHENYL SULFONES; DIFFERENT SOLVENTS; DUAL EMISSIONS; DUAL FLUORESCENCE; EMISSION QUANTUM YIELD; EMISSION SPECTRUMS; GASEOUS PHASE; INTRAMOLECULAR CHARGE TRANSFERS; LOW-ENERGY BAND; NON-RADIATIVE DEACTIVATION; OPTIMIZED GEOMETRIES; PHOTOPHYSICS; PLAUSIBLE MODEL; POLAR SOLVENTS; ROTATIONAL RELAXATIONS; SPECTRAL SHIFT; STEADY STATE; TIME-RESOLVED; TIME-RESOLVED EMISSION SPECTRA; TIME-RESOLVED EMISSION SPECTROSCOPY;

CHARGE TRANSFER; EMISSION SPECTROSCOPY; EXCITED STATES; QUANTUM YIELD;

SOLVENTS;

EID: 84857097185     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie201113b     Document Type: Article

References (64)

1. Closs, G. L.; Miller, J. R. Intramolecular Long-Distance Electron Transfer in Organic Molecules Science 1988, 240, 440-447
2. Sedghi, G.; Sawada, K.; Esdaile, L. J.; Hoffmann, M.; Anderson, H. L.; Bethell, D.; Haiss, W. S.; Higgins, J.; Nichols, R. J. Single Molecule Conductance of Porphyrin Wires with Ultralow Attenuation J. Am. Chem. Soc. 2008, 130, 8582-8583 (Pubitemid 351962478)
3. Castellón, E.; Zayat, M.; Levy, D. Molecular configuration transitions of a nematic liquid crystal encapsulated in organically modified silicas Phys. Chem. Chem. Phys. 2009, 11, 6234-6241
4. Zhao, G. J.; Liu, J. Y.; Zhou, L. C.; Han, K. L. Site-Selective Photoinduced Electron Transfer from Alcoholic Solvents to the Chromophore Facilitated by Hydrogen Bonding: A New Fluorescence Quenching Mechanism J. Phys. Chem. B 2007, 111, 8940-8945
5. Bulheller, B. M.; Miles, A. J.; Wallace, B. A.; Hirst, J. D. Charge-Transfer Transitions in the Vacuum-Ultraviolet of Protein Circular Dichroism Spectra J. Phys. Chem. B 2008, 112, 1866-1874 (Pubitemid 351316392)
6. Osawa, M.; Hoshino, M.; Wada, T.; Araki, Y.; Ito, O. Phosphorous atom induced intramolecular charge transfer fluorescence in 9- diphenylphosphinophenanthrene Chem. Phys. Lett. 2006, 427, 338-342 (Pubitemid 44189336)
7. Meric, B.; Kerman, K.; Ozkan, D.; Kara, P.; Erdem, A.; Kucukoglu, O.; Erciyas, E.; Ozsoz, M. Electrochemical biosensor for the interaction of DNA with the alkylating agent 4,4′-dihydroxy chalcone based on guanine and adenine signals J. Pharm. Biomed. Anal. 2002, 30, 1339-1346 (Pubitemid 35284342)
8. Shaoo, D.; Chakravorti, S. Orientational dynamics of a charge transfer complex in cyclodextrin cavity as receptor Phys. Chem. Chem. Phys. 2008, 10, 5890-5897
9. Shaoo, D.; Chakravorti, S. Dye-Surfactant Interaction: Modulation of Photophysics of an Ionic Styryl Dye Photochem. Photobiol. 2009, 85, 1103-1109
10. 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
11. Grabowski, Z. R. Electron transfer and the structural changes in the excited state Pure Appl. Chem. 1992, 64, 1249-1255
12. Zhao, G.-J.; Han, K.-L. pH-Controlled twisted intramolecular charge transfer (TICT) excited state via changing the charge transfer direction Phys. Chem. Chem. Phys. 2011, 12, 8914-891
13. Zhang, C.; Feng, L.; Chen, Z. Photophysical processes of some carbazole derivatives and benzimidazole derivatives Chem. Phys. Lett. 2006, 420, 330-335 (Pubitemid 43332848)
14. Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Principles of Molecular Photochemistry: An Introduction; University Science Books: CA, 2009; p 258.
15. Pal, S. K.; Peon, J.; Zewail, A. H. Biological water at the protein surface: Dynamical solvation probed directly with femtosecond resolution Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 1763-1768 (Pubitemid 34168964)
16. Wandelt, B.; Turkewitsch, P.; Stranix, B. R.; Darling, G. D. Effect of temperature and viscosity on intramolecular charge-transfer fluorescence of a 4- p -dimethylamino-styrylpyridinium salt in protic solvents J. Chem. Soc., Faraday Trans. 1995, 91, 4199-4205
17. Sahoo, D.; Bhattacharya, P.; Chakravorti, S. Quest for Mode of Binding of 2-(4- (Dimethylamino)styryl)-1-methylpyridinium Iodide with Calf Thymus DNA J. Phys. Chem. B 2010, 114, 2044-2050
18. Sahoo, D.; Bhattacharya, P.; Chakravorti, S. On the Spectral Behavior of an Ionic Styryl Dye: Effect of Micelle-Polyethylene- block -polyethylene Glycol Diblock Copolymer Assembly J. Phys. Chem. B 2009, 113, 13560-13565
19. Sahoo, D.; Bhattacharya, P.; Chakravorti, S. Reverse Micelle Induced Flipping of Binding Site and Efficiency of Albumin Protein with an Ionic Styryl Dye J. Phys. Chem. B 2010, 114, 10442-10450
20. Sahoo, D.; Chakravorti, S. Spectra and dynamics of an ionic styryl dye in reverse micelles J. Photochem. Photobiol., A 2009, 205, 129-138
21. Zgierski, M. Z.; Fujiwara, T.; Lim, E. C. Conical intersections and ultrafast intramolecular excited-state dynamics in nucleic acid bases and electron donor-acceptor molecules Chem. Phys. Lett. 2008, 463, 289-299
22. Gomes, R.; Laia, C. A. T.; Pina, F. On the Mechanism of Photochromism of 4′- N, N Dimethylamino-7-hydroxyflavylium in Pluronic F127 J. Phys. Chem. B 2009, 113, 11134-11146
23. Seddon, K. R. Ionic Liquids for Clean Technology J. Chem. Technol. Biotechnol. 1997, 68, 351-357
24. Sheldon, R. Catalytic reactions in ionic liquids Chem. Commun. 2001, 2399-2407 (Pubitemid 33124059)
25. Lakowicz, J. R. Principle of Fluorescence Spectroscopy, 3 rd ed.; Springer: New York, 2006; Chapters 1-3.
26. Dickinson, C.; Stewart, J. M.; Ammon, H. L. The X -ray crystal structure of the antimalarial and antileprotic drug 4,4 -diaminodiphenyl Sulphone J. Chem. Soc. D 1970, 920-921
27. Rettig, W.; Chandross, E. A. Dual fluorescence of 4,4′- dimethylamino- and 4,4′- diaminophenyl sulfone. Consequences of d-orbital participation in the intramolecular charge separation process J. Am. Chem. Soc. 1985, 107, 5617-5624
28. Rajendiran, N.; Swaminathan, M. Solvatochromism and prototropism of diaminodiphenyl sulphones and 2-aminodiphenyl Sulphone: a comparative study by electronic spectra J. Photochem. Photobiol., A 1995, 90, 109-116
29. Enoch, I. V. M. V.; Swaminathan, M. Unusual twisted intramolecular charge transfer processes of 4,4′-diamino-diphenylsulfone in β-cyclodextrin: a study by electronic spectra J. Chem. Res. 2006, 8, 523-526 (Pubitemid 44421859)
30. Su, S.; Simon, J. D. Solvent dynamics and twisted intramolecular charge transfer in bis(4-aminophenyl) sulfone J. Phys. Chem. 1986, 90, 6475-6479
31. Su, S.; Simon, J. D. The importance of hydrogen bonded clusters in the stabilization of the intramolecular charge transfer state of 4,4′-diaminophenyl Sulphone in alcohols and alcohol:acetonitrile mixtures Chem. Phys. Lett. 1986, 132, 345-350
32. Simon, J. D.; Su, S. Dynamic solvent effects on intramolecular electron-transfer reactions: fluctuation time scales and population decays J. Phys. Chem. 1988, 92, 2395-2397
33. Bhattacharya, P.; Sahoo, D.; Chakravorti, S. Photophysics and Structure of Inclusion Complex of 4,4-diaminodiphenyl Sulfone with Cyclodextrin Nano-Cavities Ind. Eng. Chem. Res. 2011, 50, 7815-7823
34. Berlman, I. B. Hand Book of Fluorescence Spectra of Atomic Molecules; Academic Press: New York, 1995; p 114.
35. Shaw, A. K.; Pal, S. K. Fluorescence Relaxation Dynamics of Acridine Orange in Nanosized Micellar Systems and DNA J. Phys. Chem. B 2007, 111, 4189-4199 (Pubitemid 46732969)
36. Sahoo, D.; Chakravorti, S. Influence of surfactants on the excited state photophysics of 4-nitro-1-hydroxy-2-naphthoic acid Photochem. Photobiol. Sci. 2010, 9, 1094-1100
37. Maciejewski, A.; Kubicki, J.; Dobek, K. The Origin of Time-Resolved Emission Spectra (TRES) Changes of 4-Aminophthalimide (4-AP) in SDS Micelles. The Role of the Hydrogen Bond between 4-AP and Water Present in Micelles J. Phys. Chem. B 2003, 107, 13986-13999
38. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
39. Mennucci, B.; Cancès, E.; Tomasi, J. Evaluation of Solvent Effects in Isotropic and Anisotropic Dielectrics and in Ionic Solutions with a Unified Integral Equation Method: Theoretical Bases, Computational Implementation, and Numerical Applications J. Phys. Chem. B 1997, 101, 10506-10517 (Pubitemid 127587741)
40. Klosterman, J. K.; Baldridge, K. K.; Siegel, J. S. Photophysics of manisyl-substituted 2- pyridin-2-yl-1,10-phenanthrolines. Dual emission dependent on structure and solvent Phys. Chem. Chem. Phys. 2009, 11, 5408-5415
41. Lippert, E.; Luder, W.; Moll, F.; Nagele, W.; Boos, H.; Prigge, H.; Seibold, B. I. Umwandlung von Elektronenanregungsenergi Angew. Chem. 1961, 73, 695-706
42. Cornelissen-Gude, C.; Rettig, W. Dual Fluorescence and Multiple Charge Transfer Nature in Derivatives of N -Pyrrolobenzonitrile J. Phys. Chem. A 1998, 102, 7754-7760 (Pubitemid 128611525)
43. Rettig, W.; Marschner, F. Population of excited charge-transfer states and molecularconformation in N-phenylpyrroles Nouv. J. Chim. 1983, 7, 425-431
44. Ito, F.; Nagai, T.; Ono, Y.; Yamaguchi, K.; Furuta, H.; Nagamura, T. Photophysical properties of 2-picolinoylpyrrole boron complex in solutions Chem. Phys. Lett. 2007, 435, 283-288 (Pubitemid 46178501)
45. Mataga, N.; Chosrowja, H.; Taniguchi, S. Ultrafast charge transfer in excited electronic states and investigations into fundamental problems of exciplex chemistry: Our early studies and recent developments J. Photochem. Photobiol., C 2005, 6, 37-79 (Pubitemid 40534479)
46. West, R. C. C. R C. Hand book of Chemistry and Physics, 68 th ed.; CRC Press Inc.: FL, 1987; p 88.
47. Kamlet, M. J.; Abboud, J. L. M.; Abraham, M. H.; Taft, R. W. Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, pi, alpha, and beta, and some methods for simplifying the generalized solvatochromic equation J. Org. Chem. 1983, 48, 2877-2887
48. Zhao, G.-J.; Han, K.-L. Hydrogen Bonding in the Electronic Excited State Acc. Chem. Res. DOI: 10.1021/ar200135h
49. Zhou, P.; Song, P.; Liu, J.; Han, K. L; He, G. Experimental and theoretical study of the rotational reorientation dynamics of 7-animocoumarin derivatives in polar solvents: hydrogen-bonding effects Phys. Chem. Chem. Phys. 2009, 11, 9440-9449
50. Zhao, G.-J.; Han, K.-L. Effects of Hydrogen Bonding on Tuning Photochemistry: Concerted Hydrogen-Bond Strengthening and Weakening ChemPhysChem 2008, 9, 1842-1846
51. Mennucci, B.; Caricato, M.; Ingrosso, F.; Cappelli, C.; Cammi, R.; Tomasi, J.; Scalmani, G.; Frisch, M. J. How the Environment Controls Absorption and Fluorescence Spectra of PRODAN: A Quantum-Mechanical Study in Homogeneous and Heterogeneous Media J. Phys. Chem. B 2008, 112, 414-423 (Pubitemid 351184615)
52. Sedon, K. R.; Stark, A.; Torres, M. J. In Clean Solvents: Alternative Media for Chemical Reactions and Processing; Abraham, M. M. L., Ed.; ACS Symposium Series 819, Washington, DC, 2002.
53. Karmakar, R.; Samanta, A. Solvation Dynamics of Coumarin-153 in a Room- Temperature Ionic Liquid J. Phys. Chem. A 2002, 106, 4447-4452 (Pubitemid 35290032)
54. Bangal, P. R.; Panja, S.; Chakravorti, S. Excited state photodynamics of 4- N, N -dimethylamino cinnamaldehyde: A solvent dependent competition of TICT and intermolecular hydrogen bonding J. Photochem. Photobiol., A 2001, 139, 5-16 (Pubitemid 33618396)
55. Bublitz, G. U.; Boxer, S. G. Effective Polarity of Frozen Solvent Glasses in the Vicinity of Dipolar Solutes J. Am. Chem. Soc. 1998, 120, 3988-3992 (Pubitemid 28300164)
56. Sahoo, D.; Bhattacharya, P.; Chakravorti, S. Spectral Signature of 2-[4-(Dimethylamino)styryl]-1- methylquinolinium Iodide: A Case of Negative Solvatochromism in Water J. Phys. Chem. B 2011, 115, 10983-10989
57. Bojarski, P.; Grajek, H.; śurkowska, G.; Kukliński, B.; Smyk, B.; Drabent, R. Excitation Energy Transport in a Concentrated System of Flavomononucleotide in Polyvinyl Alcohol Films J. Fluoresc. 1990, 9, 391-396
58. Rettig, W.; Koutecký, V. B. On a possible mechanism of the multiple fluorescence of p-N, N-dimethylaminobenzonitrile and related compounds Chem. Phys. Lett. 1979, 62, 115-120
59. Lippert, E.; Ayuk, A. A.; Rettig, W.; Wermuth, G. Adiabatic photoreactions in dilute solutions of p -substituted N, N -dialkylanilines and related donor-acceptor compounds J. Photochem. 1981, 17, 237-241
60. Maroncelli, M.; Fleming, G. R. Picosecond solvation dynamics of coumarin 153: The importance of molecular aspects of solvation J. Chem. Phys. 1987, 86, 6221-6239
61. Koti, A. S. R.; Krishna, M. M. G.; Periasamy, N. Time-Resolved Area-Normalized Emission Spectroscopy (TRANES): A Novel Method for Confirming Emission from Two Excited States J. Phys. Chem. A 2001, 105, 1767-1771
62. Maciejewski, A.; Kubicki, J.; Dobek, K. The Origin of Time-Resolved Emission Spectra (TRES) Changes of 4-Aminophthalimide (4-AP) in SDS Micelles. The Role of the Hydrogen Bond between 4-AP and Water Present in Micelles J. Phys. Chem. B 2003, 107, 13986-13999
63. Schanschule, R.; Parusel, A.; Koher, G. Theoretical investigations of the ground-state properties of stereoselectively substituted aminobenzonitriles J. Mol. Struct. (Theochem) 1997, 419, 161-167 (Pubitemid 127437833)
64. Frisch, M. J. Gaussian 03, revision D. 01; Gaussian, Inc.: Wallingford, CT, 2004.