Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access January 23, 2013

Spectral properties of coumarin derivatives in various environments

Alzbeta Holubekova, Pavel Mach and Jan Urban
From the journal Open Chemistry

Abstract

The structural and spectral properties of coumarin derivatives in complex environments were investigated within the time-dependent density functional theory (TD DFT). Absorption spectra calculations were obtained at TD PBE0/6-31+G(d,p) level of theory for coumarin47 in the gas-phase and in various polar and non-polar organic solvents. The geometries of coumarins 6, 30, 47 and 522 in the gas phase and in inclusion complexes with the β-cyclodextrin (βCD) were determined by PM3 and DFT (HCTH/6-31G) calculations. Encapsulation of coumarin in βCD and associated changes in electronic structure produced either a red or blue shift in the absorption spectra of coumarins. A proposed cavity model for βCD-coumarin complex in water solution allowed identification of various contributions to the overall shift in the absorption spectra of coumarin upon complex formation in a solvent environment

[1] N.C. Maiti, M.M.G. Krishna, P.J. Britto, N. Periasamy, J. Phys. Chem. B 101, 11051 (1997) http://dx.doi.org/10.1021/jp972312310.1021/jp9723123Search in Google Scholar

[2] K. Ray, A.K. Dutta, T.N. Misra, J. Lumin. 71, 123 (1997) http://dx.doi.org/10.1016/S0022-2313(96)00130-510.1016/S0022-2313(96)00130-5Search in Google Scholar

[3] J. Panyam, S.K. Sahoo, S. Prabha, T. Bargar, V. Labhasetwar, Int. J. Pharm. 262, 1 (2003) http://dx.doi.org/10.1016/S0378-5173(03)00295-310.1016/S0378-5173(03)00295-3Search in Google Scholar

[4] C.D. Grant, M.R. DeRitter, K.E. Steege, T.A. Fadeeva, E.W. Castner, Langmuir 21, 1745 (2005) http://dx.doi.org/10.1021/la047560m10.1021/la047560mSearch in Google Scholar

[5] J.A. Hamilton, L.K. Steinrauf, Acta Crystallogr. 24, 1560 (1968) http://dx.doi.org/10.1107/S056774086800463210.1107/S0567740868004632Search in Google Scholar

[6] D. Haiyun, C. Jianbin, Z. Guomei, S. Shaomin, P. Jinhao, Spectrochim. Acta A 59, 3421 (2003) http://dx.doi.org/10.1016/S1386-1425(03)00176-810.1016/S1386-1425(03)00176-8Search in Google Scholar

[7] Y. Zhang, S. Yu, F. Bao, Carbohydr. Res. 343, 2504 (2008) http://dx.doi.org/10.1016/j.carres.2008.06.02310.1016/j.carres.2008.06.023Search in Google Scholar

[8] C. Nunez-Aguero, C. Escobar-Llanos, D. Diaz, C. Jaime, R. Garduno-Juarez, Tetrahedron 62, 4162 (2006) http://dx.doi.org/10.1016/j.tet.2006.02.01010.1016/j.tet.2006.02.010Search in Google Scholar

[9] A. Bernini, O. Spiga, A. Ciutti, M. Scarselli, G. Bottoni, P. Mascagni, N. Niccolai, Eur. J. Pharm. Sci. 22, 445 (2004) http://dx.doi.org/10.1016/j.ejps.2004.04.00710.1016/j.ejps.2004.04.007Search in Google Scholar

[10] X. Wen, F. Tan, Z. Jing, Z. Liu, J. Pharm. Biomed. Anal. 34, 517 (2004) http://dx.doi.org/10.1016/S0731-7085(03)00576-410.1016/S0731-7085(03)00576-4Search in Google Scholar

[11] M.B. de Jesus, L. de Matos Alves Pinto, L.F Fraceto, Y. Takahata, A.C.S. Lino, C. Jaime, E. de Paula, J. Pharm. Biomed. Anal. 41, 1428 (2006) http://dx.doi.org/10.1016/j.jpba.2006.03.01010.1016/j.jpba.2006.03.010Search in Google Scholar PubMed

[12] C.W. Lee, S.J. Kim, Y.S. Youn, E. Widjojokusumo, Y.H. Lee, J. Kim, Y.W. Lee, R.R. Tjandrawinata, J. Supercrit. Fluids 55, 348 (2010) http://dx.doi.org/10.1016/j.supflu.2010.05.02810.1016/j.supflu.2010.05.028Search in Google Scholar

[13] D. Bonenfant, P. Niquette, M. Mimeault, A. Furtos-Matei, R. Hausler, Water Res. 43, 3575 (2009) http://dx.doi.org/10.1016/j.watres.2009.05.01010.1016/j.watres.2009.05.010Search in Google Scholar PubMed

[14] A. Abou-Okeil, A. El-Shafie, Carbohydr. Polym. 84, 593 (2011) http://dx.doi.org/10.1016/j.carbpol.2010.12.03510.1016/j.carbpol.2010.12.035Search in Google Scholar

[15] E. Ziemons, G. Dive, B. Debrus, V. Barillaro, M. Frederich, R. Lejeune, L. Angenot, L. Delattre, L. Thunus, Hubert P, J. Pharm. Biomed. Analysis. 43, 910 (2007) http://dx.doi.org/10.1016/j.jpba.2006.09.01110.1016/j.jpba.2006.09.011Search in Google Scholar PubMed

[16] V. Harabagiu, B.C. Simionescu, M. Pinteala, C. Merrienne, J. Mahuteau, P. Guegan, H. Cheradame, Carbohydr. Polym. 56, 301 (2004) http://dx.doi.org/10.1016/j.carbpol.2003.12.00710.1016/j.carbpol.2003.12.007Search in Google Scholar

[17] F. Jara, M. Domínguez, M.C. Rezende, Tetrahedron 62, 7817 (2006) http://dx.doi.org/10.1016/j.tet.2006.05.05310.1016/j.tet.2006.05.053Search in Google Scholar

[18] M.B. de Jesus, L. de Matos Alves Pinto, L.F Fraceto, Y. Takahata, A.C.S. Lino, C. Jaime, E. de Paula, J. Pharm. Biomed. Anal. 41, 1428 (2006) http://dx.doi.org/10.1016/j.jpba.2006.03.01010.1016/j.jpba.2006.03.010Search in Google Scholar

[19] J.S. Holt, J. Mol. Struct. 965, 31 (2010) http://dx.doi.org/10.1016/j.molstruc.2009.11.03410.1016/j.molstruc.2009.11.034Search in Google Scholar

[20] L. Liu, Q.X. Guo, J. Incl. Phenom. Macrocycl. Chem. 42, 1 (2002) http://dx.doi.org/10.1023/A:101452083081310.1023/A:1014520830813Search in Google Scholar

[21] M. Hillebrand, S. Ionescu, Chem. Phys. 293, 53 (2003) http://dx.doi.org/10.1016/S0301-0104(03)00289-110.1016/S0301-0104(03)00289-1Search in Google Scholar

[22] V.K. Sharma, P.D. Saharo, N. Sharma, R.C. Rastogi, S.K. Ghoshal, D. Mohan, Spectrochim. Acta A 59, 1161 (2003) http://dx.doi.org/10.1016/S1386-1425(02)00296-210.1016/S1386-1425(02)00296-2Search in Google Scholar

[23] T. Tsuji, M. Onoda, Y. Otani, T. Ohwada, T. Nakajima, K. Hirao, Chem. Phys. Lett. 473, 196 (2009) http://dx.doi.org/10.1016/j.cplett.2009.03.06610.1016/j.cplett.2009.03.066Search in Google Scholar

[24] D. Jacquemin, E.A. Perpète, X. Assfeld, G. Scalmani, M.J. Frisch, C. Adamo, Chem. Phys. Lett. 438, 208 (2007) http://dx.doi.org/10.1016/j.cplett.2007.03.00810.1016/j.cplett.2007.03.008Search in Google Scholar

[25] J. Preat, D. Jacquemin, V. Wathelet, J.M. André, E.A. Perpète, J. Phys. Chem. A 110, 8144 (2006) http://dx.doi.org/10.1021/jp061260r10.1021/jp061260rSearch in Google Scholar PubMed

[26] K. Deuk Seo, H. Min Song, M. Jun Lee, M. Pastore, C. Anselmi, F. De Angelis, M.K. Nazeeruddin, M. Gräetzel, H. Kyu Kim, Dyes Pigm. 90, 304 (2011) http://dx.doi.org/10.1016/j.dyepig.2011.01.00910.1016/j.dyepig.2011.01.009Search in Google Scholar

[27] D. Jacquemin, A. Planchat, C. Adamo, Benedetta Mennucci, J. Chem. Theory Comput. 8, 2359 (2012) http://dx.doi.org/10.1021/ct300326f10.1021/ct300326fSearch in Google Scholar PubMed

[28] R. Sánchez-de-Armas, M. A. San-Miguel, J. Oviedo, J. F. Sanz, Phys. Chem. Chem. Phys. 14, 225 (2012) http://dx.doi.org/10.1039/c1cp22058f10.1039/C1CP22058FSearch in Google Scholar

[29] B. Xu, J. Yang, X. Jiang, Y. Wang, H. Sun, J. Yin, J. Mol. Struct. 917, 15 (2009) http://dx.doi.org/10.1016/j.molstruc.2008.06.02010.1016/j.molstruc.2008.06.020Search in Google Scholar

[30] T. Sakata, Y. Kawashima, H. Nakano, Int. J. Quantum. Chem. 109, 1940 (2009) http://dx.doi.org/10.1002/qua.2201910.1002/qua.22019Search in Google Scholar

[31] W. Zhao, Y. Ding, Q. Xia, J. Comput. Chem. 32, 545 (2011) http://dx.doi.org/10.1002/jcc.2163210.1002/jcc.21632Search in Google Scholar PubMed

[32] J.A. Key, S. Koh, Q.K. Timerghazin, A. Brown, C.W. Cairo, Dyes Pigm. 82, 196 (2009) http://dx.doi.org/10.1016/j.dyepig.2009.01.00110.1016/j.dyepig.2009.01.001Search in Google Scholar

[33] W. Zhao, W. Bian, J. Mol. Struct. 859, 73 (2008) http://dx.doi.org/10.1016/j.theochem.2008.03.00410.1016/j.theochem.2008.03.004Search in Google Scholar

[34] F.H. Allen, Acta Crystallogr. 58, 380 (2002) http://dx.doi.org/10.1107/S010876810200389010.1107/S0108768102003890Search in Google Scholar PubMed

[35] HyperChem(TM) Professional 7.51 (Hypercube, Inc., 1115 NW 4th Street, Gainesville, Florida 32601, USA, 2002) Search in Google Scholar

[36] J.J.P. Stewart, J. Comput. Chem. 10, 209 (1989) http://dx.doi.org/10.1002/jcc.54010020810.1002/jcc.540100208Search in Google Scholar

[37] J.J.P. Stewart, J. Comput. Chem. 10, 221 (1989) http://dx.doi.org/10.1002/jcc.54010020910.1002/jcc.540100209Search in Google Scholar

[38] A.D. Boese, N.C. Handy, J. Chem. Phys. 114, 5497 (2001) http://dx.doi.org/10.1063/1.134737110.1063/1.1347371Search in Google Scholar

[39] C. Adamo, V. Barone, J. Chem. Phys. 110, 6158 (1999) http://dx.doi.org/10.1063/1.47852210.1063/1.478522Search in Google Scholar

[40] A.D. Becke, Phys. Rev. A 38, 3098 (1988) http://dx.doi.org/10.1103/PhysRevA.38.309810.1103/PhysRevA.38.3098Search in Google Scholar

[41] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B. 37, 785 (1988) http://dx.doi.org/10.1103/PhysRevB.37.78510.1103/PhysRevB.37.785Search in Google Scholar

[42] A.D. Becke, J. Chem. Phys. 98, 5648 (1993) http://dx.doi.org/10.1063/1.46491310.1063/1.464913Search in Google Scholar

[43] C. Hättig, F. Weigend; J. Chem. Phys. 113, 5154 (2000) http://dx.doi.org/10.1063/1.129001310.1063/1.1290013Search in Google Scholar

[44] J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 105, 2999 (2005) http://dx.doi.org/10.1021/cr990400910.1021/cr9904009Search in Google Scholar

[45] M. Cossi, G. Scalmani, N. Rega, and V. Barone, J. Chem. Phys. 117, 43 (2002) http://dx.doi.org/10.1063/1.148044510.1063/1.1480445Search in Google Scholar

[46] M. Maroncelli, L. Reynolds, M.L. Horng, J.A. Gardecki, S.J.V. Frankland, J. Phys. Chem. 100, 10337 (1996) http://dx.doi.org/10.1021/jp953110e10.1021/jp953110eSearch in Google Scholar

[47] M. Maroncelli, G.R. Fleming, J. Chem. Phys. 86, 6221 (1987) http://dx.doi.org/10.1063/1.45246010.1063/1.452460Search in Google Scholar

[48] M. Maroncelli, M.L. Horng, J.A. Gardecki, A. Papazyan, J. Phys. Chem. 99, 17311 (1995) http://dx.doi.org/10.1021/j100048a00410.1021/j100048a004Search in Google Scholar

[49] A. Broo, A. Holmén, J. Phys. Chem. A. 101, 3589 (1997) http://dx.doi.org/10.1021/jp963928f10.1021/jp963928fSearch in Google Scholar

[50] M.J. Frisch, et al., Gaussian 03, Revision D. 02 (Gaussian, Inc., Wallingford, CT, 2004) Search in Google Scholar

[51] R. Ahlrichs, M. Bar, M. Haser, H. Horn, C. Kolmel, Chem. Phys. Lett. 162,165 (1989) http://dx.doi.org/10.1016/0009-2614(89)85118-810.1016/0009-2614(89)85118-8Search in Google Scholar

[52] M.S. Zakerhamidi, A. Ghanadzadeh, M. Moghadam, Spectrochim. Acta A 78, 961 (2011) http://dx.doi.org/10.1016/j.saa.2010.12.00210.1016/j.saa.2010.12.002Search in Google Scholar PubMed

[53] M.S. Zakerhamidi, A. Ghanadzadeh, H. Tajalli, M. Moghadam, M. Jassas, R. Hosseini, Spectrochim. Acta A 77, 337 (2010) http://dx.doi.org/10.1016/j.saa.2009.12.06010.1016/j.saa.2009.12.060Search in Google Scholar PubMed

[54] T. López Arbeloa, F. López Arbeloa, M.J. Tapia, I. López Arbeloa, J. Phys. Chem. 97, 4704 (1993) http://dx.doi.org/10.1021/j100120a02410.1021/j100120a024Search in Google Scholar

[55] S. Bakkialakshmi, T. Menaka, Rec. Res. Sci. Tech. 2, 58 (2010) Search in Google Scholar

[56] C. Tablet, I. Matei, E. Pincu, V. Meltzer, M. Hillebrand, J. Mol. Liq. 168, 47 (2012) http://dx.doi.org/10.1016/j.molliq.2012.01.01610.1016/j.molliq.2012.01.016Search in Google Scholar

[57] M. Nowakowska, M. Smoluch, D. Sendor, J. Incl. Phenom. Macrocycl. Chem. 40, 213 (2001) http://dx.doi.org/10.1023/A:101182051325610.1023/A:1011820513256Search in Google Scholar

Published Online: 2013-1-23
Published in Print: 2013-4-1

© 2013 Versita Warsaw

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

Scroll Up Arrow