European Journal of Chemistry

Determination of excited singlet-state dipole moments of hydroxy and methoxy coumarins using solvatochromic method



Main Article Content

Mohd Mudassir Husain
Rajeev Sindhu
Harmesh Chander Tandon

Abstract

The effects of solvents of various polarity on the electronic absorption and fluorescence spectra of 7-hydroxy-4-trifluoromethyl coumarin; 6,7-dihydroxy-4-trifluoromethyl coumarin and 7-methoxy-4-trifluoromethyl coumarin have been investigated. The singlet-state excited dipole moments (μe) and ground state dipole moments (μg) are estimated from Bakshiev and Kawski-Chamma-Viallet equations by using the variation of Stokes’ shift with the solvent’s dielectric constant (ε) and refractive index (n). The observed singlet-state excited dipole moments are found to be larger than the ground-state ones. In addition, the geometry and other electronic properties are computed using ab-initio method with correlation functions at 6-31G basis set.

3_1_75_80_800


icon graph This Abstract was viewed 2126 times | icon graph Article PDF downloaded 884 times

How to Cite
(1)
Husain, M. M.; Sindhu, R.; Tandon, H. C. Determination of Excited Singlet-State Dipole Moments of Hydroxy and Methoxy Coumarins Using Solvatochromic Method. Eur. J. Chem. 2012, 3, 75-80.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Fletcher, A. N.; Bliss, D. E. Appl. Phys. 1978, 16, 289-295.
http://dx.doi.org/10.1007/BF00885124

[2]. Halstead, J. A.; Reeves, R. R. Opt. Commun. 1978, 27, 273-276.
http://dx.doi.org/10.1016/0030-4018(78)90379-6

[3]. Gardecki, J. A.; Maroncelli, M. J. Phys. Chem. 1999, 103, 1187-1197.

[4]. Levinger, N. E. Curr. Opin. Colloid Interf. Sci. 2000, 5, 118-124.
http://dx.doi.org/10.1016/S1359-0294(00)00044-3

[5]. Castner, J. E. W.; Kennedy, D.; Cave, R. J. J. Phys. Chem. A 2000, 104, 2869-2885.
http://dx.doi.org/10.1021/jp9936852

[6]. Morandeira, A.; Fulrstenberg, A.; Vauthey, E. J. Phys. Chem. A 2004, 108, 8190-8200.
http://dx.doi.org/10.1021/jp048048c

[7]. Kumbhakar, M.; Nath, S.; Mukherjee, T.; Pal, H. J. Chem. Phys 2004, 121, 6026-6033.

[8]. Wattenburg, L. W.; Lam, L. K.; Fladmore, A. V. Cancer Res. 1999, 39, 1651-1654.

[9]. Cassady, J. M.; Ojima, N.; Chang, C. J.; Mcloughlin, J. L. J. Nat. Prod. 1979, 42, 274-278.
http://dx.doi.org/10.1021/np50003a005
PMid:490172

[10]. Finnegan, R. A.; Merkel, K. E.; Back, N. J. Pharm. Sci. 1972, 61, 1599-1603.
http://dx.doi.org/10.1002/jps.2600611011
PMid:4672389

[11]. Giri, R.; Rathi, S. S.; Machwe, M. K. Spectrochim. Acta A 1992, 48, 843-848.
http://dx.doi.org/10.1016/0584-8539(92)80080-G

[12]. Moriya, T. Bull. Chem. Soc. Jpn. 1984, 57, 1723-1730.
http://dx.doi.org/10.1246/bcsj.57.1723

[13]. EI-Ansary, A. L.; Ebeid, E. M.; Omar, M. M. Spectrochim. Acta A 1987, 43, 709-710.

[14]. Schulman, S. G. (Ed.), Molecular Luminescence Spectroscopy, Methods and Applications, Wiley, New York, 1985.

[15]. Kumar, S.; Rao, V. C.; Rastogi, R. C. Spectrochim. Acta Part A 2001, 57, 41-47.
http://dx.doi.org/10.1016/S1386-1425(00)00330-9

[16]. Sharma, V. K.; Saharo, P. D.; Rastogi, R. C. Spectrochim. Acta A 2003, 59, 1161-1170.
http://dx.doi.org/10.1016/S1386-1425(02)00296-2

[17]. Murray, R. D. H. Natl. Prod. Rep. 1989, 6, 591-624.
http://dx.doi.org/10.1039/np9890600591
PMid:2699016

[18]. Ravi, M.; Soujanya, T.; Samanta, A.; Radhakrishnan, T. P. J. Chem. Soc. Faraday Trans. 1995, 91, 2739-2742.
http://dx.doi.org/10.1039/ft9959102739

[19]. Mannekutla, J. R.; Mulimani, B. G.; Inamdar, S. R. Spectochim. Acta A 2008, 69, 419-426.
http://dx.doi.org/10.1016/j.saa.2007.04.016
PMid:17540614

[20]. Aaron, J. J.; Buna, M.; Parkanyi, C.; Antonious, M. S.; Tine, A. J. Fluoresc. 1995, 5, 337-348.
http://dx.doi.org/10.1007/BF01152560

[21]. Onager, L. J. Am. Chem. Soc. 1936, 58, 1482-1486.
http://dx.doi.org/10.1021/ja01299a049

[22]. Kirkwood, J. G. J. Chem. Phys. 1939, 7, 911-919.

[23]. Nadaf, Y. D.; Deshpande, D. K.; Karaguppikar, A. M.; Inamdar, S. R. J. Photosci. 2002, 9, 29-35.

[24]. Kawski, A. Z. Natureforsch. 2002, 57A, 255-262.

[25]. Evale, B. G.; Hanagodimath, S. M.; Khan, I. A.; Kulkarni, M. V. Spectochim. Acta A 2009, 73, 694-700.
http://dx.doi.org/10.1016/j.saa.2009.03.016
PMid:19410501

[26]. Thipperudrappa, J.; Biradar, D. S.; Manohara, S. R.; Hangodimath, S. M.; S. R. Inamdar, S. R Spectrochim. Acta A 2008, 69, 991-997.
http://dx.doi.org/10.1016/j.saa.2007.06.002
PMid:17714982

[27]. Siddlingeshwar, B.; Hanagodimath, S. M. Spectrochim. Acta A 2009, 72, 490-495.
http://dx.doi.org/10.1016/j.saa.2008.10.020
PMid:19056310

[28]. Raikar, U. S.; Renuka, C. G.; Nadaf, Y. F.; Mulimani, B. G.; Karguppikar, A. M.; Soudagar, M. K. Spectrochim. Acta A 2006, 65, 673-677.
http://dx.doi.org/10.1016/j.saa.2005.12.028
PMid:16524762

[29]. Kumar, S.; Jain, S. K.; Rastogi, R. C Spectrochim. Acta A 2001, 57, 291-298.
http://dx.doi.org/10.1016/S1386-1425(00)00372-3

[30]. Cisse, L.; Djande, A.; Capo-Chichi, M.; Aaron, J. J. Spectrochim. Acta A 2011, 79, 428-436.
http://dx.doi.org/10.1016/j.saa.2011.02.053
PMid:21511517

[31]. Zakerhamidi, M. S.; Ghanadzadeh, A.; Moghadam, M. Spectrochim. Acta A 2011, 78, 961-966.
http://dx.doi.org/10.1016/j.saa.2010.12.002
PMid:21227741

[32]. Inamdar, S. R.; Nadaf, Y. F.; Mulimani, B. G. J. Mol. Struct. 2003, 624, 47-51.

[33]. Zakerhamidi, M. S.; Ghanadzadeh, A.; Moghadam, M.; Tajalli, H. Spectrochim. Acta A 2010, 77, 767-772.
http://dx.doi.org/10.1016/j.saa.2010.07.013
PMid:20702133

[34]. Siddlingeshwar, B.; Hanagodimath, S. M.; Kirilova, E. M. J. Quant. Spectrosc. Radiat. Trans. 2011, 112, 448-456.
http://dx.doi.org/10.1016/j.jqsrt.2010.09.001

[35]. Jozefowicz, M.; Milart, P.; Heldt, J. R. Spectrochim. Acta A 2009, 74, 959-963.
http://dx.doi.org/10.1016/j.saa.2009.08.050
PMid:19782635

[36]. Sundstrom, V.; Gilbro, T. Chem. Phys. Lett. 1984, 109, 538-543.
http://dx.doi.org/10.1016/0009-2614(84)85420-2

[37]. HYPERCHEM 7. 52, Hypercube Inc., Florida, 2003.

[38]. Lippert, E. Z. Naturforch, Part A 1955, 10, 541-545.

[39]. Lippert, E. Elektrochem, Ber. Bunsenges. Phys. Chem. 1957, 61, 962-975.

[40]. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-470.
http://dx.doi.org/10.1246/bcsj.29.465

[41]. Mataga, N.; Kubota, T. Molecular Interactions and Electronic Spectra, Dekker, New York, 1970.

[42]. Bakshiev, N. G. Opt. Spektosk. (USSR) 1964, 16, 821-832.

[43]. Chamma, A.; Viallet, P. C. R. Acad. Sci. Paris, Ser. C 1970, 270, 1901-1904.

[44]. Suppan, P. Chem. Phys. Lett. 1983, 94, 272-275.
http://dx.doi.org/10.1016/0009-2614(83)87086-9

[45]. Ghazy, R.; Azim, S. A,; Shaheen, M. F. El-Mekawey Spectrochim. Acta A 2004, 60, 187-191.
http://dx.doi.org/10.1016/S1386-1425(03)00205-1

[46]. Zachariasse, K. Private communication, 6th International Conference on Solar Energy and Applied Photochemistry, “Solar’01”, 3-8 April 2001, Cairo.

[47]. Lide, D. R. CRC Handbook of Chemistry and Physics, 79th Edn. CRC.

[48]. Mitnik, D. J. Mol. Struct. (Theochem) 2009, 911, 105-108.
http://dx.doi.org/10.1016/j.theochem.2009.07.006

[49]. Fukui, K.; Yonezawa, T.; Shingu, H. J. Chem. Phys. 1952, 20, 722-725.

[50]. Pearson, R. G. J. Org. Chem. 1989, 54, 1423-1430.
http://dx.doi.org/10.1021/jo00267a034

[51]. Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1990, 112, 5720-5724.
http://dx.doi.org/10.1021/ja00171a007

[52]. Faust, W. L. Science 1989, 245, 37-42.
http://dx.doi.org/10.1126/science.245.4913.37
PMid:17787990

[53]. Rafie, H.; Bahget Ali, H. Can. J. Chem. 1985, 63, 1173-1179.
http://dx.doi.org/10.1139/v85-200

[54]. Agmon, N. J. Phys. Chem. A 2005, 109, 13-35.
PMid:16839085

Supporting Agencies

Department of Applied Sciences and Humanities, Faculty of Engineering and Technology, Jamia Millia Islamia, New Delhi, India
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).