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

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.3.2.163-171.538

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1641 times | icon graph PDF Article downloaded 454 times

Funding information


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

Citations

/


[1]. 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
/

[2]. Eleonora-Mihaela Ungureanu, Marian-Laurentiu Tatu, Emilian Georgescu, Cristian Boscornea, Marcel-Mirel Popa, Gabriela Stanciu
Influence of the chemical structure and solvent polarity on the fluorescence of 3-aryl-7-benzoyl-pyrrolo [1,2-c]pyrimidines
Dyes and Pigments  174, 108023, 2020
DOI: 10.1016/j.dyepig.2019.108023
/

[3]. G. V. Muddapur, N. R. Patil, S. S. Patil, R. M. Melavanki, R. A. Kusanur
“Estimation of Ground and Excited State Dipole Moments of aryl Boronic acid Derivative by Solvatochromic Shift Method”
Journal of Fluorescence  24(6), 1651, 2014
DOI: 10.1007/s10895-014-1452-6
/

[4]. S.K. Patil, M.N. Wari, C. Yohannan Panicker, S.R. Inamdar
Determination of ground and excited state dipole moments of dipolar laser dyes by solvatochromic shift method
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy  123, 117, 2014
DOI: 10.1016/j.saa.2013.12.031
/

[5]. Jorge Alamán, María López-Valdeolivas, Raquel Alicante, Carlos Sánchez-Somolinos
Optical Planar Waveguide Sensor with Integrated Digitally-Printed Light Coupling-in and Readout Elements
Sensors  19(13), 2856, 2019
DOI: 10.3390/s19132856
/

[6]. Hassan Hasan Hammud, Mohammad Hasan El-Dakdouki, Nada Mohamd Sonji, Kamal Hani Bouhadir
Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides
European Journal of Chemistry  6(3), 325, 2015
DOI: 10.5155/eurjchem.6.3.325-336.1282
/

[7]. H.R. Deepa, J. Thipperudrappa, H.M. Suresh Kumar
Effect of solvents on the spectroscopic properties of LD-489 & LD-473: Estimation of ground and excited state dipole moments by solvatochromic shift method
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy  108, 288, 2013
DOI: 10.1016/j.saa.2013.01.084
/

[8]. Manisha Sharma, Uttam Pal, Mamta Kumari, Damayanti Bagchi, Swati Rani, Dipanjan Mukherjee, Arpan Bera, Samir Kumar Pal, Tanusree Saha Dasgupta, Subho Mozumdar
Effect of solvent on the photophysical properties of isoxazole derivative of curcumin: A combined spectroscopic and theoretical study
Journal of Photochemistry and Photobiology A: Chemistry  410, 113164, 2021
DOI: 10.1016/j.jphotochem.2021.113164
/

[9]. Mamta Kumari, Manisha Sharma, Swati Rani, Damayanti Bagchi, Arpan Bera, Dipanjan Mukherjee, Samir Kumar Pal, Subho Mozumdar
Solvent dependent photophysical study of stable and medicinally active diketone modified pyrazole derivatives of curcumin: A spectroscopic study
Journal of Photochemistry and Photobiology A: Chemistry  416, 113337, 2021
DOI: 10.1016/j.jphotochem.2021.113337
/

[10]. Arnaud Chevalier, Pierre-Yves Renard, Anthony Romieu
Straightforward Access to Water-Soluble Unsymmetrical Sulfoxanthene Dyes: Application to the Preparation of Far-Red Fluorescent Dyes with Large Stokes’ Shifts
Chemistry - A European Journal  20(27), 8330, 2014
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. 24 Oct. 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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.3.2.163-171.538

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)




© Copyright 2010 - 2021 • 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 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.