European Journal of Chemistry 2012, 3(1), 87-93. doi:10.5155/eurjchem.3.1.87-93.519

Photophysical properties and estimation of ground and excited state dipole moments of 7-diethylamino and 7-diethylamino-4-methyl coumarin dyes from absorption and emission spectra


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: 05 Sep 2011, Accepted: 24 Oct 2011, Published: 31 Mar 2012

Abstract


In the present work, the effect of solvents on absorption and fluorescence spectra and dipole moments (μg, μe) of 7-diethylamino coumarin (7DEAC) and 7-diethylamino-4-methyl coumarin (7DEA4MC) have been studied in different solvents of various polarity at room temperature. The solvents have been selected in a way to cover the full range of intermolecular interactions from non-polar hexane to strongly polar formamide. Using the methods of solvatochromism, the difference in the first excited singlet-state (μe) and ground state (μg) dipole moments was estimated from Lippert-Mataga, Bakhshiev, Kawski-Chamma-Viallet and McRae equations. The Onsager’s cavity radius of the probes has been calculated by AM1 and PM3 quantum chemical calculations and also by a direct relation. The change in dipole moment value (Δμ) was also calculated by using the variation of Stoke’s shift with microscopic solvent polarity parameter (ETN). The calculated dipole moments represent new results, as well as some of the solvatochromic results that were not studied earlier in such large number of solvents. It is observed that the values of excited singlet-state dipole moments are higher than the ground state ones in both the molecules, which shows that excited states are more polar than the ground states.

3_1_87_93_800


Keywords


Coumarins; Absorption; Stoke’s shift; Fluorescence; Dipole moment; Onsager’s cavity radius

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.3.1.87-93.519

Article Metrics


This Abstract was viewed 1357 times | PDF Article downloaded 372 times

Citations

/


[1]. Archana A. Bhagwat, Nagaiyan Sekar
Fluorescent 7-Substituted Coumarin Dyes: Solvatochromism and NLO Studies
Journal of Fluorescence  29(1), 121, 2019
DOI: 10.1007/s10895-018-2316-2
/


[2]. Sanjay Kumar, Vinita Kapoor, Ritu Bansal, H.C. Tandon
Ground and excited state dipole moments of some flavones using solvatochromic methods: An experimental and theoretical study
Journal of Molecular Structure  1156, 308, 2018
DOI: 10.1016/j.molstruc.2017.11.113
/


[3]. Xiaogang Liu, Jacqueline M. Cole, Kian Sing Low
Solvent Effects on the UV–vis Absorption and Emission of Optoelectronic Coumarins: a Comparison of Three Empirical Solvatochromic Models
The Journal of Physical Chemistry C  117(28), 14731, 2013
DOI: 10.1021/jp310397z
/


[4]. Mateo I. Sánchez, José Martínez-Costas, José L. Mascareñas, M. Eugenio Vázquez
MitoBlue: A Nontoxic and Photostable Blue-Emitting Dye That Selectively Labels Functional Mitochondria
ACS Chemical Biology  9(12), 2742, 2014
DOI: 10.1021/cb500552f
/


[5]. Shivaram N. Patil, F.M. Sanningannavar, B.S. Navati, N.R. Patil, R.A. Kusanur, R.M. Melavanki
Photophysical characteristics of two novel coumarin derivatives: Experimental and theoretical estimation of dipole moments using the solvatochromic shift method
Canadian Journal of Physics  92(11), 1330, 2014
DOI: 10.1139/cjp-2013-0685
/


[6]. Prashant S. Deore, Daniel S. Coman, Richard A. Manderville
A coumarin–hemicyanine hybrid as a ratiometric fluorescent sensor of microenvironment proticity
Chemical Communications  55(24), 3540, 2019
DOI: 10.1039/C8CC10132A
/


[7]. Archana A. Bhagwat, Kiran C. Avhad, Dinesh S. Patil, Nagaiyan Sekar
Design and Synthesis of Coumarin–Imidazole Hybrid Chromophores: Solvatochromism, Acidochromism and Nonlinear Optical Properties
Photochemistry and Photobiology  95(3), 740, 2019
DOI: 10.1111/php.13024
/


[8]. Manoj M. Jadhav, Towhid H. Chowdhury, Idriss Bedja, Dinesh Patil, Ashraful Islam, Nagaiyan Sekar
Near IR emitting novel rhodanine-3-acetic acid based two donor-π-acceptor sensitizers for DSSC: Synthesis and application
Dyes and Pigments  165, 391, 2019
DOI: 10.1016/j.dyepig.2019.02.045
/


[9]. V. P. Andreev, P. S. Sobolev, D. O. Zaitsev, S. M. Timofeeva
Effect of the Solvent on the Coordination of Pyridine Derivatives with Zn Tetraphenylporphine
Russian Journal of General Chemistry  88(10), 2108, 2018
DOI: 10.1134/S1070363218100134
/


[10]. N. Cabaleiro, I. de la Calle, C. Bendicho, I. Lavilla
Coumarins as turn on/off fluorescent probes for detection of residual acetone in cosmetics following headspace single-drop microextraction
Talanta  129, 113, 2014
DOI: 10.1016/j.talanta.2014.05.033
/


[11]. Manoj M. Jadhav, Dinesh Patil, Nagaiyan Sekar
Highly Stoke shifted near infrared (NIR) emitting donor-pi-acceptor chromophore: Synthesis and combined experimental and computational studies of photophysical properties
Journal of Photochemistry and Photobiology A: Chemistry  363, 13, 2018
DOI: 10.1016/j.jphotochem.2018.05.028
/


[12]. Rafael López-Arteaga, Anne B. Stephansen, Cesar A. Guarin, Theis I. Sølling, Jorge Peon
The Influence of Push–Pull States on the Ultrafast Intersystem Crossing in Nitroaromatics
The Journal of Physical Chemistry B  117(34), 9947, 2013
DOI: 10.1021/jp403602v
/


[13]. Naresh Kumar, Jagdeep Kumar, Prasanta Kumar Hota
Substituent Dependence Charge Transfer and Photochemical Properties of Donor-Acceptor Substituted Ethenyl Thiophenes
Journal of Fluorescence  27(5), 1729, 2017
DOI: 10.1007/s10895-017-2111-5
/


[14]. Nejla Khatir–Hamdi, Malika Makhloufi-Chebli, Hocine Grib, Meziane Brahimi, Artur M.S. Silva
Synthesis DFT/TD-DFT theoretical studies and experimental solvatochromic shift methods on determination of ground and excited state dipole moments of 3-(2-hydroxybenzoyl) coumarins
Journal of Molecular Structure  1175, 811, 2019
DOI: 10.1016/j.molstruc.2018.08.039
/


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 Jr., 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]. Schitschek, E. J.; Trias, J. A.; Hammond, P. R.; Henry, R. A.; Atkins, R. L. Opt. Commun. 1976, 16, 313-316.
http://dx.doi.org/10.1016/0030-4018(76)90005-5

[9]. Parkyani, C.; Antonius, M. S.; Aaron, J. J.; Buna, M.; Tine, A.; Cisse L. Spectrosc. Lett. 1994, 27, 439-449.
http://dx.doi.org/10.1080/00387019408007249

[10]. Shermon, W. R.; Robins, E. Anal. Chem. 1968, 40, 803-805.
http://dx.doi.org/10.1021/ac60260a045
PMid:5641323

[11]. 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

[12]. 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

[13]. 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

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

[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]. Cremers, D. A.; Windsor, M. W. Chem. Phys. Lett. 1980, 71, 27-32.
http://dx.doi.org/10.1016/0009-2614(80)85283-3

[17]. Balu, W.; Reber, R.; Penzkofer, A. Opt. Commun. 1982, 43, 210-214.
http://dx.doi.org/10.1016/0030-4018(82)90348-0

[18]. Sundstrom, V.; Gillbro, T.; Bergstrom, H. Chem. Phys. 1982, 73, 439-458.
http://dx.doi.org/10.1016/0301-0104(82)85183-5

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

[20]. Bilot, L.; Kawski, A. Z. Naturforsch. 1962, 179, 621-627

[21]. Kawski, A.; Rabek, J. F. Progress in photochemistry and photophysics, Vol. 5., Boca Raton USA, CRC Press, 1992.

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

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

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

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

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

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

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

[29]. McRae, E. G. J. Phys. Chem. 1957, 61, 562-572.
http://dx.doi.org/10.1021/j150551a012

[30]. 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

[31]. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim, 1988.

[32]. Ravi, M.; Samanta, A.; Radhakrishnan, T. P. J. Phys. Chem. 1994, 98, 9133-9136.
http://dx.doi.org/10.1021/j100088a007

[33]. Hasegawa, M.; Suzuki, Y.; Suzuki, F.; Nakaniski, H. J. Polym. Sci. A 1969, 7, 743-752

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

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

[36]. Diraison, M.; Millie, P.; Mialoq, Gustavsson, T. Chem. Phys. Letts. 1998, 282, 152-158.
http://dx.doi.org/10.1016/S0009-2614(97)01194-9

[37]. McCarthy, P. K.; Blanchard, G. J. J. Phys. Chem. 1993, 97, 12205-12209.
http://dx.doi.org/10.1021/j100149a018

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

[39]. DeMelo, J. S. S.; Becker, R. S.; Mocarita, A. I. J. Phys. Chem. 1994, 98, 6054-6058.
http://dx.doi.org/10.1021/j100075a002

[40]. Gayathri, B. R.; Mannekutla, J. R.; Inamdar, S. R. J. Mol. Struct. 2008, 889, 383-393.
http://dx.doi.org/10.1016/j.molstruc.2008.02.020

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


How to cite


Husain, M.; Sindhu, R.; Tandon, H. Eur. J. Chem. 2012, 3(1), 87-93. doi:10.5155/eurjchem.3.1.87-93.519
Husain, M.; Sindhu, R.; Tandon, H. Photophysical properties and estimation of ground and excited state dipole moments of 7-diethylamino and 7-diethylamino-4-methyl coumarin dyes from absorption and emission spectra. Eur. J. Chem. 2012, 3(1), 87-93. doi:10.5155/eurjchem.3.1.87-93.519
Husain, M., Sindhu, R., & Tandon, H. (2012). Photophysical properties and estimation of ground and excited state dipole moments of 7-diethylamino and 7-diethylamino-4-methyl coumarin dyes from absorption and emission spectra. European Journal of Chemistry, 3(1), 87-93. doi:10.5155/eurjchem.3.1.87-93.519
Husain, Mohd, Rajeev Sindhu, & Harmesh Chander Tandon. "Photophysical properties and estimation of ground and excited state dipole moments of 7-diethylamino and 7-diethylamino-4-methyl coumarin dyes from absorption and emission spectra." European Journal of Chemistry [Online], 3.1 (2012): 87-93. Web. 14 Nov. 2019
Husain, Mohd, Sindhu, Rajeev, AND Tandon, Harmesh. "Photophysical properties and estimation of ground and excited state dipole moments of 7-diethylamino and 7-diethylamino-4-methyl coumarin dyes from absorption and emission spectra" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

DOI Link: https://doi.org/10.5155/eurjchem.3.1.87-93.519

Refbacks

  • 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.