Steady-State and Time-Resolved Fluorescence Studies of Anthrylacrylic Ester

Abstract

The photophysical properties of Anthrylacrylic ester were investigated in various solvents using steady-state and time-resolved fluorescence techniques. The dual fluorescence was observed in various solvents of different polarity functions. The emission bands observed are around 400 nm (band I) and 480 nm (band II) for 350 nm and 390 nm excitation at low concentrations (10–5 mol·dm–3) but at higher concentrations (10–3 mol·dm–3) only the emission (band II) at 480 nm alone was observed. The emission band observed around 400 nm shifts from 390 nm to 420 nm (shift 30 nm) when the excitation wavelength was varied from 300 nm to 380 nm and the emission band at 480 nm shifts from 430 nm to 510 nm (shift 80 nm) for the change of excitation wavelength from 380 nm to 400 nm. However, both emissions were observed for 380 nm excitation at lower concentrations. Solvatochromic shifts of electronic absorption and fluorescence emissions (band I & II) as a function of polarity functions were analyzed and the changes in dipole moment of the molecule was estimated (Δμ = 3.36 D & 5.98 D). Fluorescence decays monitored over each emission maxima showed bi-exponential behavior, and yielded two lifetime components respectively in the range 0.97 - 7.1 ns (at λem = 400 nm) and 0.34 - 7.23 ns (at λem = 480 nm). Based on the steady-state and time-resolved emission measurements emission band I (400 nm) and emission band II (480 nm) are respectively assigned as due to locally excited state (Trans-forms) and due to isomers (Cis-form).

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A. B. Naik, L. R. Naik, V. Jayathirtha Rao and H. Pal, "Steady-State and Time-Resolved Fluorescence Studies of Anthrylacrylic Ester," Open Journal of Physical Chemistry, Vol. 2 No. 4, 2012, pp. 212-220. doi: 10.4236/ojpc.2012.24029.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] E. Lippert, W. Ludar and H. Boss., “Advances in Molecular Spectroscopy,” Pergamon Press, Oxford, 1962.
[2] S. K. Saha, P. Purkayastha, A. B. Das and S. Dhara, “Excited State Isomerization and Effect of Viscosity and Temperature-Dependent Torsional Relaxation on TICT Fluorescence of Trans-2-[4-(Dimethylamino)Styryl] Benzothiazole,” Journal of Photochemistry and Photobiology A: Chemistry, Vol. 199, No. 2-3, 2008, pp. 179-187
[3] A. Chakraborty, S. Kar and N. Guchhait, “Photophysical Properties of Trans-3-(4-Monomethylamino-Phenyl)-Acrylonitrile: Evidence of Twisted Intramolecular Charge Transfer (TICT) Process,” Chemical Physics, Vol. 324, No. 2-3, 2006, pp. 733-774. doi:10.1016/j.chemphys.2005.12.032
[4] R. B. Singh, S. Mahanta, S. Kar and N. Guchhait, “Spectroscopic and Theoretical Evidence for the Photoinduced Twisted Intramolecular Charge Transfer State Formation in N,N-Dimethylaminonaphthyl-(Acrylo)-Nitrile,” Journal of Luminescence, Vol. 128, No. 9, 2008 pp. 1421-1430. doi:10.1016/j.jlumin.2008.01.015
[5] Z. R. Grabowski, K. Rotkiewicz and A. Siemiarezak, “Dual Fluorescence of Donor-Acceptor Molecules and the Twisted Intramolecular Charge Transfer (TICT) States,” Journal of Luminescence, Vol. 18-19, 1979, pp. 420-424. doi:10.1016/0022-2313(79)90153-4
[6] J. Catalan, C. Diaz, V. lopez, P. Perez and R. M. Claramunt, “The TICT Mechanism in 9,9’-Biaryl Compounds: Solvatochromism of 9,9’-Bianthryl, N-(9-Anthryl) Carbazole, and N,N’-Bicarbazyl,” The Journal of Physical Chemistry, Vol. 100, No. 47, 1996, pp. 183-192.
[7] C. Rulliere, Z. R. Grabowski and J. Dobkowski, “Picosecond Absorption Spectra of Carbonyl Derivatives of Dimethylaniline: The Nature of the Tict Excited States,” Chemical Physics Letters, Vol. 137, No. 5, 1987, pp. 408-413. doi:10.1016/0009-2614(87)80224-5
[8] K. A. Zachariasse, ‘‘Comment on Pseudo-Jahn-Teller and TICT-Models: A Photophysical Comparison of Meta-and Para-DMABN Derivatives: The PICT Model for Dual Fluorescence of Aminobenzonitriles,’’ Chemical Physics Letters, Vol. 320, No. 1-2, 2000, pp. 8-13. doi:10.1016/S0009-2614(00)00230-X
[9] A. Sobolewski and W. Domcke, ‘‘Charge Transfer in Aminobenzonitriles: Do They Twist,” Chemical Physics Letters, 250, No. 3-4, 1996, pp. 428-436. doi:10.1016/0009-2614(96)00014-0
[10] L. R. Naik, A. B. Naik and H. Pal, ‘‘Steady-State and Time-Resolved Emission Studies of Thioflavin-T,” Journal of Photochemistry and Photobiology A: Chemistry, Vol. 204, No. 2-3, 2009, pp. 161-167. doi:10.1016/j.jphotochem.2009.03.016
[11] V. R. Gopal., M. Reddy and V. J. Rao, ‘‘Wavelength Dependent Trans to Cis and Quantum Chain Isomerizations of Anthrylethylene Derivatives,” The Journal of Organic Chemistry, Vol. 60, No. 24, 1995, pp. 7966-7973. doi:10.1021/jo00129a043
[12] L. R. Naik and N. N. Math, “Photo Physical Properties of 8-Hydroxy Quinoline,” Indian Journal of Pure & Applied Physics, Vol. 43, 2005, pp. 743-749.
[13] M. Kumbhakar, S. Nath, T. Mukherjee and H. Pal, “Effect of Temperature on the Dynamics of Electron Transfer in Heterogeneous Medium: Evidence for Apparent Marcus Inversion,” Journal of Photochemistry and Photobiology A: Chemistry, Vol. 182, No. 1, 2006, pp. 7-12. doi:10.1016/j.jphotochem.2006.01.005
[14] S. A. Rani, J. Sobhanadri and T. A. P. Rao, “Solvent and Concentration Effects on the Steady State Fluorescence of Fluorenone,” Journal of Photochemistry and Photobiology A: Chemistry, Vol. 94, No. 1, 1996, pp. 1-5. doi:10.1016/1010-6030(95)04114-1
[15] M. Ravi, A. Samanta, and T. P. Radhakrishnan, “Excited State Dipole Moments from an Efficient Analysis of Solvatochromic Stokes Shift Data,” The Journal of Physical Chemistry, Vol. 98, No. 37, 1994, pp. 9133-9136. doi:10.1021/j100088a007
[16] C. Antonious, M. S. Aaron, J. J. Buna, M. Tine, A and L. Cisse, “Determination of the First Excited Singlet State Dipole Moments of Coumarins by the Solvatochromic Method,” Spectroscopy Letters, Vol. 27, No. 4, 1994, pp. 439-449.
[17] B. Acemioglu, M. Arik, H. Efeoglu and Y. Onganer, “Solvent Effect on the Ground and Excited State Dipole Moments of Fluorescein,” Journal of Molecular Structure: Theochem, Vol. 548, No. 1-3, 2001, pp. 165-171. doi:10.1016/S0166-1280(01)00513-9
[18] M. P. Haas and J. M. Warman, “Photon-Induced Molecular Charge Separation Studied by Nanosecond Time-Resolved Microwave Conductivity,” Chemical Physics, Vol. 73, No. 1-2, 1982, pp. 35-53. doi:10.1016/0301-0104(82)85148-3
[19] A. Kawaski, ‘‘On the Estimation of Excited-State Dipole Moments from Solvatochromic Shifts of Absorption and Fluorescence Spectra,” Z. Naturforsch, Vol. 57A, 2002, pp. 255-262.
[20] L. R. Naik, and N. N. Math, “Estimation of Ground and Excited State Dipole Moments of Coumarin 450 by Solvatochromic Shift Method,” Journal of Photosceince, Vol. 12, No. 2, 2005, pp. 57-61.
[21] R. C. Weast “Hand book of Chemistry,” 68th Edition, CRC Press, Boca Raton, 1987.
[22] P. Suppan, “Excited-State Dipole Moments from Absorption/Fluorescence Solvatochromic Ratios,” Chemical Physics Letters, Vol. 94, No. 3, 1983, pp. 272-275. doi:10.1016/0009-2614(83)87086-9
[23] S. Kumar, V. C. Raoand and R. C. Rastogi, “Excited-State Dipole Moments of Some Hydroxycoumarin Dyes Using an Efficient Solvatochromic Method Based on the Solvent Polarity Parameter, ETN,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 57, No. 1, 2001, pp. 41-47. doi:10.1016/S1386-1425(00)00330-9
[24] M. Ravi, T. Soujanya, A. Samantha and T. P. Radhakrishna, “Excited-State Dipole Moments of Some Coumarin dyes from a Solvatochromic Method Using the Solvent Polarity Parameter, ETN,” Journal of the Chemical Society, Faraday Transactions, Vol. 91, 1995, pp. 2739-2742. doi:10.1039/ft9959102739
[25] R. Giri, S. S. Rathi, M. K. Machwe and V. V. S. Murti, “Solvent and Substituent Effects: Depolarization of Fluorescence of Solutions of 4-Phenyl-6,7-Dimethoxy Coumarin,” Indian Journal of Pure & Applied Physics, Vol. 28, No. 6, 1988, pp. 445-448.
[26] L. R. Naik, H. M. Suresh Kumar, S. R. Inamdar and N. N. Math, “Steady-state and time-resolved emission studies of 6-methoxy quinoline,” Spectroscopy Letters, Vol. 38, No. 4-5, 2005, pp. 645-659. doi:10.1081/SL-200062818
[27] A. B. Naik, L. R. Naik, J. S. Kadadevarmath, P. Haridas and V. J. Rao, “Fluorescence Quenching of Anthrylvinyl Acetate by Carbon Tetrachloride,” Journal of Photochemistry and Photobiology A: Chemistry, Vol. 214, No. 2-3, 2010, pp. 145-151.

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