European Journal of Chemistry 2012, 3(2), 163-171 | doi: https://doi.org/10.5155/eurjchem.3.2.163-171.538 | Get rights and content

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Solvent effect on the spectral properties of dipolar laser dyes: Evaluation of ground and excited state dipole moments


Kakkabevinahalli Hadagalli Nagachandra (1) , J. R. Mannekutla (2) , Shivkumar Math Amarayya (3) , Sanjeev Ramchandra Inamdar (4,*)

(1) Department of Physics, Banashankari Arts, Commerce and Shantikumar Gubbi Science College, Dharwad, 580004, India
(2) Combustion Research Laboratory, Department of General Energy, Paul Scherrer Institute, CH-5232 Villigen PSI, Switzerland
(3) Laser Spectroscopy Programme, Department of Physics, Karnatak University, Dharwad, 580003, India
(4) Laser Spectroscopy Programme, Department of Physics, Karnatak University, Dharwad, 580003, India
(*) Corresponding Author

Received: 15 Oct 2011 | Accepted: 26 Dec 2011 | Published: 30 Jun 2012 | Issue Date: June 2012

Abstract


The effect of solvents on absorption and fluorescence spectra and dipole moments of two medium sized dipolar laser dyes 2-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl) benzoic acid (Fluorescein 27) (F27) and N-[6-diethylamino)-9-(2,4-disulfophenyl)-3H-xanthen-3-ylidene]-N-ethylhydroxid (Sulfarhodamine B) (SRB) have been studied comprehensively in polar protic and polar aprotic solvents at room temperature (298 K). The bathochromic shift observed in absorption and fluorescence spectra of F27 and SRB with increasing solvent polarity signifies that the transition involved are π→π*. Solvatochromic correlations were used to obtain the ground and excited state dipole moments. The observed excited state dipole moments are found to be larger than their ground state counterparts in all the solvents studied. The ground and excited state dipole moments of these probes have also been computed from ab initio calculations and compared with those determined experimentally. Further, the experimentally obtained changes in dipole moment (Δμ) were compared with those using normalized polarity terms  from Reichardt equation.

3_2_163_171_800

 


Keywords


Dipolar dyes; Stokes’ shift; Solvatochromic; Solvent polarity; Bathochromic shift; Ground and excited state dipole moments

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DOI: 10.5155/eurjchem.3.2.163-171.538

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University Grants Commission-South West Regional Office, Bangalore, New Delhi, India

Citations

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[3]. G. V. Muddapur, N. R. Patil, S. S. Patil, R. M. Melavanki, R. A. Kusanur
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DOI: 10.1007/s10895-014-1452-6
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DOI: 10.5155/eurjchem.6.3.325-336.1282
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DOI: 10.1016/j.saa.2013.01.084
/


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DOI: 10.1016/j.jphotochem.2021.113164
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[9]. Arnaud Chevalier, Pierre-Yves Renard, Anthony Romieu
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DOI: 10.1002/chem.201402306
/


References


[1]. Reichradt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd edition, Wiley-VCH, Verlag, GmbH and Co., 2004.

[2]. Acemioglu, B.; Arik, M.; Efeoglu, H.; Onganer, Y. J. Mol. Struct. (Theochem) 2001, 548, 165-171.
http://dx.doi.org/10.1016/S0166-1280(01)00513-9

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

[4]. Adeoye, M. D.; Adeogun, A. I.; Adewui, S.; Odozi, N. W.; Obi-Egbeedi, N. O. Sci. Res. Essays 2009, 4, 107-111.

[5]. Inamdar, S. R.; Nadaf, Y. F.; Mulimani, B. G. J. Mol. Struct. (Theochem) 2003, 624, 47-51.
http://dx.doi.org/10.1016/S0166-1280(02)00734-0

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

[7]. Rautela, R.; Joshi, N. K.; Joshi, H. C.; Tewari, N.; Pant, S. J. Mol. Liq. 2010, 154, 47-51.
http://dx.doi.org/10.1016/j.molliq.2010.04.004

[8]. Tewari, N.; Joshi, N. K.; Rautela, R.; Gahlaut, R.; Joshi, H. C.; Pant, S. J. Mol. Liq. 2011, 160, 150-153.
http://dx.doi.org/10.1016/j.molliq.2011.03.008

[9]. Gahlaut, R.; Tewari, N.; Bridhkoti, J. P.; Joshi, N. K.; Joshi, H. C.; Pant, S. J. Mol. Liq. 2011, 163, 141-146.
http://dx.doi.org/10.1016/j.molliq.2011.08.010

[10]. Bevilaqua, T.; Goncalves, T. F.; Venturini, C. G.; Machado, V. G. Spectochim. Acta A 2006, 65, 535-545.
http://dx.doi.org/10.1016/j.saa.2005.12.005
PMid:16524763

[11]. Oliveira, C. S.; Bronco, K. P.; Baptista, M. S.; Indig, G. L. Spectochim. Acta A 2002, 58, 2971-2982.
http://dx.doi.org/10.1016/S1386-1425(02)00044-6

[12]. Ishikawa, M.; Ye, J. Y.; Maruyama, Y.; Nakatsuka, H. J. Phys. Chem. A 1999, 103, 4319-4331.
http://dx.doi.org/10.1021/jp984650p

[13]. El-Kemary, M. A.; Khedr, R. A.; Etaiw, S. H. Spectochim. Acta A 2002, 58, 3011-3014.
http://dx.doi.org/10.1016/S1386-1425(02)00087-2

[14]. Jedrzejewska, B.; Kabatc, J.; Paczkowski, J. Dyes Pigm. 2007, 74(2), 262-268.
http://dx.doi.org/10.1016/j.dyepig.2006.02.003

[15]. Czekalla, J. Z. Electrochem. 1960, 64, 1221-1228.

[16]. Liptay, W. Dipole moments and Polarizibilities of Molecules in Excited States, in E. C. Lim, Ed., Excited States, Vol. 1, pp. 129-229, Academic Press, New York, 1974.

[17]. Baumann, W. Determination of Dipole Moments in Ground and Excited States, in Rossiter, B. W.; Hamilton, J. F., Eds., Methods of Chemistry, Vol. 3B, pp. 45-131, John Wiley and Sons, New York, 1989.

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

[19]. Lindqvist, L. Arkiv Kemi. 1960, 16, 79-138.

[20]. Koochesfahani, M. M.; Dimotakis, P. E. J. Fluid Mech. 1986, 170, 83-112.
http://dx.doi.org/10.1017/S0022112086000812

[21]. Dahm, W. J. A.; Southerland, K. B.; Buch, K. A. Phys. Fluids A 1991, 3, 1115-1127.
http://dx.doi.org/10.1063/1.858093

[22]. Karasso, P. S.; Mungal, M. G. Exp Fluids 1997, 23, 382-387.
http://dx.doi.org/10.1007/s003480050125

[23]. Schafer, F. P. Dye Lasers, Springer-Verlag, Berlin, 1973.
http://dx.doi.org/10.1007/3-540-51558-5

[24]. Demas, J. M.; Grossby, G. A. J. Phys. Chem. 1971, 75(8), 911-1024.

[25]. Yu, H. G.; Kim, M. J.; Oh, F. S. Ocul. Immunol. Inflamm. 2009, 17(1), 41-46.
http://dx.doi.org/10.1080/09273940802553279
PMid:19294573

[26]. Voigt, W. Methods Mol. Med. 2005, 110, 39-48.
PMid:15901925

[27]. 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

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

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

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

[31]. Srividya, N.; Ramamurthy, P.; Ramakrishnan, V. T. Spectrochim. Acta A 1997, 53, 1743-1753.
http://dx.doi.org/10.1016/S1386-1425(97)00091-7

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

[33]. Kawski, A. Z. Naturforsch. A 2002, 57a, 255-262.

[34]. Blanchard, G. J. J. Phys. Chem. 1988, 92, 6303-6307.
http://dx.doi.org/10.1021/j100333a026

[35]. Kamlet, M. J.; Abboud, J. M.; Taft, R. W. Prog. Phys. Org. Chem. 1981, 13, 485-630.
http://dx.doi.org/10.1002/9780470171929.ch6

[36]. Fowler, F. W.; Katritzky, A. R.; Rutherford, R. J. D. J. Chem. Soc. B 1971, 460-469.
http://dx.doi.org/10.1039/j29710000460

[37]. Abboud, J. M.; Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1977, 99, 8325-8327.
http://dx.doi.org/10.1021/ja00467a039

[38]. Kamlet, M. J.; Jones, M. E.; Taft, R. W. J. Chem. Soc. Perkin Trans. 1979, 2, 349-356.
http://dx.doi.org/10.1039/p29790000349

[39]. Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1976, 98, 377-383.
http://dx.doi.org/10.1021/ja00418a009

[40]. Lippert, E. Z. Naturforsch. A 1955, 10, 541-545.

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

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

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

[44]. Kawski, A. Progress in photochemistry and photophysics, Ed. Rabek, J. F., CRC Press Boca Raton, Boston, Vol. V. pp. 1-47, 1992 and references therein.

[45]. Bilot, L.; Kawski, A. Z. Naturforsch. 1962, 17a, 621-627.

[46]. Kawski, A. Acta Phys. Polon. 1966, 29, 507-518.

[47]. Kawski, A. Acta. Phys. Polon. 1964, 25(2), 285-290.

[48]. Kamlet, J. M.; Abboud, J. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
http://dx.doi.org/10.1021/jo00165a018

[49]. Marcus, Y. Chem. Soc. Rev. 1993, 22, 409-416.
http://dx.doi.org/10.1039/cs9932200409

[50]. Reichrardt, C. Chem. Rev. 1994, 94, 2319-2358.
http://dx.doi.org/10.1021/cr00032a005

[51]. Nagarajan, V.; Brearley, A. N.; Tai, J. K.; Barbara, P. F. J. Chem. Phys. 1987, 86, 3183-3196.

[52]. Kahlow, M. A.; Tai, J. K.; Barbara, P. F. J. Chem. Phys. 1988, 88, 2372-2378.

[53]. Reichrardt, C. (ed). Molecular interactions. Wiley, New York, 1982.

[54]. Edward, J. T. J. Chem. Edu. 1970, 47, 261-270.
http://dx.doi.org/10.1021/ed047p261

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

[56]. Gaussian 03, Revision C.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; Gaussian, Inc., Wallingford CT, 2004.

[57]. Aaron, J. J.; Maafi, M.; Parkanyi, C.; Boniface, C. Spectrochim. Acta A 1995, 51, 603-6171.
http://dx.doi.org/10.1016/0584-8539(94)00164-7


How to cite


Nagachandra, K.; Mannekutla, J.; Amarayya, S.; Inamdar, S. Eur. J. Chem. 2012, 3(2), 163-171. doi:10.5155/eurjchem.3.2.163-171.538
Nagachandra, K.; Mannekutla, J.; Amarayya, S.; Inamdar, S. Solvent effect on the spectral properties of dipolar laser dyes: Evaluation of ground and excited state dipole moments. Eur. J. Chem. 2012, 3(2), 163-171. doi:10.5155/eurjchem.3.2.163-171.538
Nagachandra, K., Mannekutla, J., Amarayya, S., & Inamdar, S. (2012). Solvent effect on the spectral properties of dipolar laser dyes: Evaluation of ground and excited state dipole moments. European Journal of Chemistry, 3(2), 163-171. doi:10.5155/eurjchem.3.2.163-171.538
Nagachandra, Kakkabevinahalli, J. R. Mannekutla, Shivkumar Math Amarayya, & Sanjeev Ramchandra Inamdar. "Solvent effect on the spectral properties of dipolar laser dyes: Evaluation of ground and excited state dipole moments." European Journal of Chemistry [Online], 3.2 (2012): 163-171. Web. 5 Mar. 2021
Nagachandra, Kakkabevinahalli, Mannekutla, J., Amarayya, Shivkumar, AND Inamdar, Sanjeev. "Solvent effect on the spectral properties of dipolar laser dyes: Evaluation of ground and excited state dipole moments" European Journal of Chemistry [Online], Volume 3 Number 2 (30 June 2012)

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