European Journal of Chemistry 2012, 3(1), 75-80. doi:10.5155/eurjchem.3.1.75-80.498

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

Mohd Mudassir Husain (1,*) , Rajeev Sindhu (2) , Harmesh Chander Tandon (3)

(1) Physics Section, Department of Applied Sciences and Humanities, Faculty of Engineering and Technology, Jamia Millia Islamia, a Central University, New Delhi-110025, India
(2) New Green Field College of Engineering and Technology, Palwal, Haryana-121102, India
(3) Department of Chemistry, Sri Venketswara College, Delhi University, New Delhi-110021, India
(*) Corresponding Author

Received: 02 Aug 2011, Accepted: 12 Aug 2011, Published: 31 Mar 2012


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.



Coumarins; Absorption; Stokes’ shift; Fluorescence; Dipole moment; Solvatochromic

Full Text:

PDF /    /

DOI: 10.5155/eurjchem.3.1.75-80.498

Article Metrics

This Abstract was viewed 986 times | PDF Article downloaded 332 times



[1]. Abeer N. Al-romaizan, Mahmoud A. Hussein
A New Candidate Laser Dye Based 1,4-Bis[β-(2-Naphthothiazolyle)Vinyl]Benzene. Spectroscopic Behavior, Laser Parameters and Excitation Energy Transfer
Journal of Fluorescence  28(3), 743, 2018
DOI: 10.1007/s10895-018-2236-1

[2]. Jana Basavaraja, S.R. Inamdar, H.M. Suresh Kumar
Solvents effect on the absorption and fluorescence spectra of 7-diethylamino-3-thenoylcoumarin: Evaluation and correlation between solvatochromism and solvent polarity parameters
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy  137, 527, 2015
DOI: 10.1016/j.saa.2014.08.118

[3]. Beena Varghese, Saleh N. Al-Busafi, FakhrEldin O. Suliman, Salma M. Z. Al-Kindy
3(2H)-Furanone as a promising scaffold for the synthesis of novel fluorescent organic dyes: an experimental and theoretical investigation
New Journal of Chemistry  39(8), 6667, 2015
DOI: 10.1039/C5NJ00842E

[4]. Tamara Bezrodna, Anatoliy Negryiko, Volodymyr Bezrodnyi, Lyudmyla Kosyanchuk
Dipole moments of phenalenone dyes determined in liquid and polymer polar media
Journal of Molecular Liquids  267, 89, 2018
DOI: 10.1016/j.molliq.2018.02.071

[5]. Vladimíra Tomečková, Beáta Veliká, Sanjay Malhotra, Miroslava Revická, Pál Perjési
Determination of Excited Singlet-State Dipole Moments of Methoxy and Dimethylamino Substituted Benzylidenebenzosuberones Using Solvatochromic Method
Spectroscopy Letters  48(5), 317, 2015
DOI: 10.1080/00387010.2014.881378

[6]. Volodymyr Bezrodnyi, Мarina Stratilat, Lyudmyla Kosyanchuk, Аnatoly Negriyko, Georgiy Klishevych, Тamara Todosiichuk
Solvation effects on spectral and photophysical properties of phenalenone dyes in polyurethane polymers
Journal of Polymer Research  23(6), , 2016
DOI: 10.1007/s10965-016-0987-4

[7]. Jana Basavaraja, H.M. Suresh Kumar, S.R. Inamdar, M.N. Wari
Estimation of ground and excited state dipole moment of laser dyes C504T and C521T using solvatochromic shifts of absorption and fluorescence spectra
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy  154, 177, 2016
DOI: 10.1016/j.saa.2015.10.020

[8]. R. M. Johann
Indicating pressure and environmental effects by means of the spectral shift with rhodamine B and fluorescein
AIP Advances  5(7), 077175, 2015
DOI: 10.1063/1.4927687

[9]. L.F. Kosyanchuk, M.S. Stratilat, N.V. Kozak, T.V. Bezrodna
Effects of polyurethane polymer polarity on spectral and photophysical properties of phenalenone dyes. Dipole moment estimations for the ground and excited states
Polymer journal  37(4), 354, 2015
DOI: 10.15407/polymerj.37.04.354

[10]. M.M. Makhlouf, H.M. Zeyada
Synthesis, structural analysis, spectrophotometric measurements and semiconducting properties of 3-phenyl azo-4-hydroxycoumarin thin films
Synthetic Metals  211, 1, 2016
DOI: 10.1016/j.synthmet.2015.10.019


[1]. Fletcher, A. N.; Bliss, D. E. Appl. Phys. 1978, 16, 289-295.

[2]. Halstead, J. A.; Reeves, R. R. Opt. Commun. 1978, 27, 273-276.

[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.

[5]. Castner, J. E. W.; Kennedy, D.; Cave, R. J. J. Phys. Chem. A 2000, 104, 2869-2885.

[6]. Morandeira, A.; Fulrstenberg, A.; Vauthey, E. J. Phys. Chem. A 2004, 108, 8190-8200.

[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.

[10]. Finnegan, R. A.; Merkel, K. E.; Back, N. J. Pharm. Sci. 1972, 61, 1599-1603.

[11]. Giri, R.; Rathi, S. S.; Machwe, M. K. Spectrochim. Acta A 1992, 48, 843-848.

[12]. Moriya, T. Bull. Chem. Soc. Jpn. 1984, 57, 1723-1730.

[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.

[16]. Sharma, V. K.; Saharo, P. D.; Rastogi, R. C. Spectrochim. Acta A 2003, 59, 1161-1170.

[17]. Murray, R. D. H. Natl. Prod. Rep. 1989, 6, 591-624.

[18]. Ravi, M.; Soujanya, T.; Samanta, A.; Radhakrishnan, T. P. J. Chem. Soc. Faraday Trans. 1995, 91, 2739-2742.

[19]. Mannekutla, J. R.; Mulimani, B. G.; Inamdar, S. R. Spectochim. Acta A 2008, 69, 419-426.

[20]. Aaron, J. J.; Buna, M.; Parkanyi, C.; Antonious, M. S.; Tine, A. J. Fluoresc. 1995, 5, 337-348.

[21]. Onager, L. J. Am. Chem. Soc. 1936, 58, 1482-1486.

[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.

[26]. Thipperudrappa, J.; Biradar, D. S.; Manohara, S. R.; Hangodimath, S. M.; S. R. Inamdar, S. R Spectrochim. Acta A 2008, 69, 991-997.

[27]. Siddlingeshwar, B.; Hanagodimath, S. M. Spectrochim. Acta A 2009, 72, 490-495.

[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.

[29]. Kumar, S.; Jain, S. K.; Rastogi, R. C Spectrochim. Acta A 2001, 57, 291-298.

[30]. Cisse, L.; Djande, A.; Capo-Chichi, M.; Aaron, J. J. Spectrochim. Acta A 2011, 79, 428-436.

[31]. Zakerhamidi, M. S.; Ghanadzadeh, A.; Moghadam, M. Spectrochim. Acta A 2011, 78, 961-966.

[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.

[34]. Siddlingeshwar, B.; Hanagodimath, S. M.; Kirilova, E. M. J. Quant. Spectrosc. Radiat. Trans. 2011, 112, 448-456.

[35]. Jozefowicz, M.; Milart, P.; Heldt, J. R. Spectrochim. Acta A 2009, 74, 959-963.

[36]. Sundstrom, V.; Gilbro, T. Chem. Phys. Lett. 1984, 109, 538-543.

[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.

[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.

[45]. Ghazy, R.; Azim, S. A,; Shaheen, M. F. El-Mekawey Spectrochim. Acta A 2004, 60, 187-191.

[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.

[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.

[51]. Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1990, 112, 5720-5724.

[52]. Faust, W. L. Science 1989, 245, 37-42.

[53]. Rafie, H.; Bahget Ali, H. Can. J. Chem. 1985, 63, 1173-1179.

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

How to cite

Husain, M.; Sindhu, R.; Tandon, H. Eur. J. Chem. 2012, 3(1), 75-80. doi:10.5155/eurjchem.3.1.75-80.498
Husain, M.; Sindhu, R.; Tandon, H. Determination of excited singlet-state dipole moments of hydroxy and methoxy coumarins using solvatochromic method. Eur. J. Chem. 2012, 3(1), 75-80. doi:10.5155/eurjchem.3.1.75-80.498
Husain, M., Sindhu, R., & Tandon, H. (2012). Determination of excited singlet-state dipole moments of hydroxy and methoxy coumarins using solvatochromic method. European Journal of Chemistry, 3(1), 75-80. doi:10.5155/eurjchem.3.1.75-80.498
Husain, Mohd, Rajeev Sindhu, & Harmesh Chander Tandon. "Determination of excited singlet-state dipole moments of hydroxy and methoxy coumarins using solvatochromic method." European Journal of Chemistry [Online], 3.1 (2012): 75-80. Web. 21 Sep. 2019
Husain, Mohd, Sindhu, Rajeev, AND Tandon, Harmesh. "Determination of excited singlet-state dipole moments of hydroxy and methoxy coumarins using solvatochromic method" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

DOI Link:


  • There are currently no refbacks.

Copyright (c)

© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.