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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access June 17, 2010

Spectroscopic evaluation of chiral and achiral fluorescent ionic liquids

Hadi Marwani
From the journal Open Chemistry


In this study, spectroscopic investigation of chiral and achiral room temperature ionic liquids is achieved. New ionic liquids were prepared via metathesis, accomplished by the reaction of either L-phenylalanine ethyl ester hydrochloride, chlorpromazine hydrochloride or 1,10-Phenanthroline monohydrate hydrochloride with lithium bis(trifluoromethane) sulfonamide in water. The resulting ionic liquids were produced in high yield and purity. The results obtained by use of 1H NMR and IR experiments were in very good agreement with the chemical structures of the synthesized ionic liquids. In addition, the results of thermal gravimetric analysis suggested that these ionic liquids have good thermal stability. UV-Vis and fluorescence spectroscopy measurements indicated that these ionic liquids are strongly optically absorbent and fluorescent. Lastly, time-based fluorescence steady-state measurements demonstrated the high photostability of these ionic liquids.

[1] K.A. Fletcher, I.A. Storey, A.E. Hendricks, S. Pandey, S. Pandey, Green Chem. 3, 210 (2001) in Google Scholar

[2] G.A. Baker, S.N. Baker, S. Pandey, F.V. Bright, Analyst 130, 800 (2005) in Google Scholar PubMed

[3] S. Pandey, Anal. Chim. Acta 556, 38 (2006) in Google Scholar PubMed

[4] T. Welton, Chemical Reviews 99, 2071 (1999) in Google Scholar PubMed

[5] C.D. Tran, S.H.P. Lacerda, Anal. Chem. 74, 5337 (2002) in Google Scholar PubMed

[6] C.D. Tran, S.H.P. Lacerda, D. Oliveira, Appl. Spectrosc. 57, 152 (2003) in Google Scholar PubMed

[7] J. Levillain, G. Dubant, I. Abrunhosa, M. Gulea, A.C. Gaumont, Chem. Commun. 2914 (2003) 10.1039/b308814fSearch in Google Scholar PubMed

[8] V.E. Dickinson, M.E. Williams, S.M. Hendrickson, H. Masui, R.W. Murray, J. Am. Chem. Soc. 121, 613 (1999) in Google Scholar

[9] J. Dupont, R.F. de Souza, P.A.Z. Suarez, Chem. Rev. 102, 3667 (2002) in Google Scholar PubMed

[10] M.L. Dietz, J.A. Dzielawa, Chem. Commun. 2124 (2001) 10.1039/b104349hSearch in Google Scholar PubMed

[11] S.G. Kazarian, B.J. Briscoe, T. Welton, Chem. Commun. 2047 (2000) 10.1039/b005514jSearch in Google Scholar

[12] J.A. Laszlo, D.L. Compton, Biotechnol. Bioeng. 75, 181 (2001) in Google Scholar PubMed

[13] C.D. Tran, D. Oliveira, Anal. Biochem. 356, 51 (2006) in Google Scholar PubMed

[14] B.M. Quinn, Z. Ding, R. Moulton, A.J. Bard, Langmuir 18, 1734 (2002) in Google Scholar

[15] A.E. Visser, R.P. Swatloski, R.D. Rogers, Green Chem. 2, 1 (2000) in Google Scholar

[16] S.M. Mwongela, A. Numan, N.L. Gill, R.A. Agbaria, I.M. Warner, Anal. Chem. 75, 6089 (2003) in Google Scholar PubMed

[17] J.L. Anderson, J. Ding, T. Welton, D.W. Armstrong, J. Am. Chem. Soc. 124, 14247 (2002) in Google Scholar PubMed

[18] A. Tholey, M. Zabet-Moghaddam, E. Heinzle, Anal. Chem. 78, 291 (2006) in Google Scholar PubMed

[19] L. Yu, D. Garcia, R. Ren, X. Zeng, Chem. Comm. 2277 (2005) 10.1039/b501224dSearch in Google Scholar PubMed

[20] C.D. Tran, D. Oliveira, S. Yu, Anal. Chem. 78, 1349 (2006) in Google Scholar PubMed

[21] J. Ding, T. Welton, W. Armstrong Daniel, Anal. Chem. 76, 6819 (2004) in Google Scholar

[22] D.K. Bwambok, H.M. Marwani, V.E. Fernand, S.O. Fakayode, M. Lowry, I. Negulescu, R. Strongin, I.M. Warner, Chirality 20, 151 (2008) in Google Scholar

[23] C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A. Gaumont, J. Plaquevent, Tetrahedron Asym. 14, 3081 (2003) in Google Scholar

[24] J. Ding, D.W. Armstrong, Chirality 17, 281 (2005) in Google Scholar

[25] J. Howarth, K. Hanlon, D. Fayne, P. McCormac, Tetrahedron Lett. 38, 3097 (1997) in Google Scholar

[26] D. Wei, A. Ivaska, Anal. Chim. Acta 607, 126 (2008) in Google Scholar PubMed

[27] J.L. Anderson, D.W. Armstrong, G.-T. Wei, Anal. Chem. 78, 2893 (2006) 10.1021/ac069394oSearch in Google Scholar PubMed

[28] P.K. Mandal, S. Saha, R. Karmakar, A. Samanta, Curr. Sci. 90, 301 (2006) Search in Google Scholar

[29] A. Samanta, J. Phys. Chem. B 110, 13704 (2006) in Google Scholar PubMed

[30] P.K. Chowdhury, M. Halder, L. Sanders, T. Calhoun, J.L. Anderson, D.W. Armstrong, X. Song, J.W. Petrich, J. Phys. Chem. B 108, 10245 (2004) in Google Scholar

[31] P.K. Mandal, A. Samanta, J. Phys. Chem. B 109, 15172 (2005) in Google Scholar PubMed

[32] B. Lang, G. Angulo, E. Vauthey, J. Phys. Chem. A 110, 7028 (2006) in Google Scholar

[33] M. Halder, L.S. Headley, P. Mukherjee, X. Song, J.W. Petrich, J. Phys. Chem. A 110, 8623 (2006) in Google Scholar

[34] A.K. Abdul-Sada, A.M. Greenway, K.R. Seddon, T. Welton, Org. Mass Spectrom. 27, 648 (1992) in Google Scholar

[35] P.B. Hitchcock, K.R. Seddon, T. Welton, J. Chem. Soc., Dalton Trans. 2639 (1993) 10.1039/dt9930002639Search in Google Scholar

[36] A.J. Dent, K.R. Seddon, T. Welton, J. Chem. Soc., Chem. Commun. 315 (1990) 10.1039/c39900000315Search in Google Scholar

[37] P. Bonhôte, A.P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Grätzel, M. Armand, Inorg. Chem. 35, 1168 (1996) in Google Scholar

[38] A.J. Carmichael, K.R. Seddon, J. Phys. Org. Chem. 13, 591 (2000)<591::AID-POC305>3.0.CO;2-210.1002/1099-1395(200010)13:10<591::AID-POC305>3.0.CO;2-2Search in Google Scholar

[39] K. Binnemans, Chem. Rev. 107, 2592 (2007) in Google Scholar

[40] Y.U. Paulechka, G.J. Kabo, A.V. Blokhin, A.S. Shaplov, E.I. Lozinskaya, D.G. Golovanov, K.A. Lyssenko, A.A. Korlyukov, Y.S. Vygodskii, J. Phys. Chem. B 113, 9538 (2009) in Google Scholar

[41] J.R. Lakowicz, Principles of Fluorescence Spectroscopy, 2nd edition (Kluwer Academic/Plenum Press, New York, 1999) 10.1007/978-1-4757-3061-6Search in Google Scholar

[42] K.A. Fletcher, S. Pandey, I.K. Storey, A.E. Hendricks, S. Pandey, Anal. Chim. Acta 453, 89 (2002) in Google Scholar

[43] P.M. Page, T.A. McCarty, G.A. Baker, S.N. Baker, F.V. Bright, Langmuir 23, 843 (2007) in Google Scholar

[44] S.V. Dzyuba, R.A. Bartsch, Tetrahedron Lett. 43, 4657 (2002) in Google Scholar

[45] L. Jie, L. Yuwen, S. Jingyan, W. Zhiyong, H. Ling, Y. Xi, W. Cunxin, Thermochim. Acta 467, 20 (2008) in Google Scholar

Published Online: 2010-6-17
Published in Print: 2010-8-1

© 2010 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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