Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access September 27, 2011

High Stokes shift long-wavelength energy gap regulated fluorescence in the series of nitro/dimethylamino-substituted ortho-analogs of POPOP

Rodion Iliashenko, Olexiy Zozulia and Andrey Doroshenko
From the journal Open Chemistry

Abstract

A series of novel nitro-substituted ortho-analogs of POPOP was synthesized. Like the most of the other known compounds of this class, the synthesized molecules demonstrate high Stokes shift fluorescence emission owing to the planarization of their molecules at electronic excitation. Significant fluorescence quenching in polar solvents was described as the “energy gap law” action rather than the specific effect of the dialkylamino group excited state twisting.

[1] J.R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd edition (Springer Science + Business Media, LLC, Singapore, 2006) http://dx.doi.org/10.1007/978-0-387-46312-410.1007/978-0-387-46312-4Search in Google Scholar

[2] B. Valeur, Molecular Fluorescence (Wiley-VCH Verlag GmbH, Weinheim, 2002) Search in Google Scholar

[3] C. Parker, Photoluminescence in solutions (Elsevier, Amsterdam-London-New York, 1968) Search in Google Scholar

[4] M. Eichhorn, Appl. Phys. B 96, 369 (2009) http://dx.doi.org/10.1007/s00340-009-3395-110.1007/s00340-009-3395-1Search in Google Scholar

[5] S.P. Nighswander-Rempel, J. Riesz, J. Gilmore, J.P. Bothma, P. Meredith, J. Phys. Chem. B 109, 20629 (2005) http://dx.doi.org/10.1021/jp053704+10.1021/jp053704+Search in Google Scholar

[6] C.H. Hidrovo, R.R. Brau, D.P. Hart, Appl. Opt. 43, 894 (2004) http://dx.doi.org/10.1364/AO.43.00089410.1364/AO.43.000894Search in Google Scholar

[7] R. Sóti, É. Farkas, M. Hilbert, Zs. Farkas, I. Ketskeméty, J. Lumin. 55, 5 (1993) http://dx.doi.org/10.1016/0022-2313(93)90077-Z10.1016/0022-2313(93)90077-ZSearch in Google Scholar

[8] F. Vollmer, W. Rettig, E. Birckner, J. Fluor. 4, 65 (1994) http://dx.doi.org/10.1007/BF0187665710.1007/BF01876657Search in Google Scholar PubMed

[9] A.O. Doroshenko, Theor. Exper. Chem. 38, 135 (2002) http://dx.doi.org/10.1023/A:101969670076310.1023/A:1019696700763Search in Google Scholar

[10] J.B. Birks, The Theory and Practice of Scintillation Counting (Pergamon Press, London, Macmillan, New York, 1964) 10.1016/B978-0-08-010472-0.50010-0Search in Google Scholar

[11] B.M. Krasovitskii, B.M. Bolotin, Organic luminescent materials (VCH Publishers, Weinheim, New York, 1988) Search in Google Scholar

[12] A.O. Doroshenko, L.D. Patsenker, V.N. Baumer, L.V. Chepeleva, A.V. Van’Kevich, A.V. Kirichenko, S.N. Yarmolenko, V.M. Shershukov, V.G. Mitina, O.A. Ponomaryov, Molec. Engineering 3, 353 (1994) http://dx.doi.org/10.1007/BF0100375910.1007/BF01003759Search in Google Scholar

[13] A.O. Doroshenko, V.N. Baumer, A.V. Kirichenko, V.M. Shershukov, A.V. Tolmachev, Chem. Heterocycl. Comp. 33, 1341 (1997) http://dx.doi.org/10.1007/BF0232033910.1007/BF02320339Search in Google Scholar

[14] A.O. Doroshenko, A.V. Kyrychenko, V.N. Baumer, A.A. Verezubova, L.M. Ptyagina, J. Molec. Struct. 524, 289 (2000) http://dx.doi.org/10.1016/S0022-2860(00)00405-110.1016/S0022-2860(00)00405-1Search in Google Scholar

[15] A.O. Doroshenko, V.N. Baumer, A.A. Verezubova, L.M. Ptyagina, J. Molec. Struct. 609, 29 (2002) http://dx.doi.org/10.1016/S0022-2860(01)00889-410.1016/S0022-2860(01)00889-4Search in Google Scholar

[16] A.O. Doroshenko, A.V. Kirichenko, V.G. Mitina, O.A. Ponomaryov, J. Photochem. Photobiol. A: Chem. 94, 15 (1996) http://dx.doi.org/10.1016/1010-6030(95)04203-210.1016/1010-6030(95)04203-2Search in Google Scholar

[17] A.V. Kirichenko, A.O. Doroshenko, V.M. Shershukov, Chem. Phys. Reports 17, 1643 (1998) Search in Google Scholar

[18] A.O. Doroshenko, A.V. Kyrychenko, J. Waluk, J. Fluor. 10, 41 (2000) http://dx.doi.org/10.1023/A:100943562958910.1023/A:1009435629589Search in Google Scholar

[19] A.O. Doroshenko, Chem. Phys. Reports 18, 873 (1999) 10.1007/s002990050677Search in Google Scholar

[20] A.O. Doroshenko, Russ. Journ. Phys. Chem. 74, 773 (2000) Search in Google Scholar

[21] A.O. Doroshenko, T.V. Sakhno, A.V. Kyrychenko, Spec. Lett. 35, 171 (2002) http://dx.doi.org/10.1081/SL-12000380310.1081/SL-120003803Search in Google Scholar

[22] W.A. Melhuish, J. Phys. Chem. 65, 229 (1961) http://dx.doi.org/10.1021/j100820a00910.1021/j100820a009Search in Google Scholar

[23] J.N. Demas, A.W. Adamson, J. Phys. Chem. 75, 2463 (1971) http://dx.doi.org/10.1021/j100685a00910.1021/j100685a009Search in Google Scholar

[24] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision E.01 (Gaussian, Inc., Wallingford, CT, 2004) Search in Google Scholar

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

[26] D.E. Woon, T.H. Dunning, J. Chem. Phys. 98, 1358 (1993) http://dx.doi.org/10.1063/1.46430310.1063/1.464303Search in Google Scholar

[27] M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S.J. Su, T.L. Windus, M. Dupuis, J.A. Montgomery, J. Comput. Chem. 14, 1347 (1993) M.J. Frisch, G.W. Trucks http://dx.doi.org/10.1002/jcc.54014111210.1002/jcc.540141112Search in Google Scholar

[28] H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, L. Martin., K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.01, (Gaussian Inc., Wallingford CT, 2009) Search in Google Scholar

[29] Y. Zhao, D.G. Truhlar, Theor. Chem. Acc. 120, 215 (2008) http://dx.doi.org/10.1007/s00214-007-0310-x10.1007/s00214-007-0310-xSearch in Google Scholar

[30] E.J. Bylaska, W.A. de Jong, N. Govind, K. Kowalski, T.P. Straatsma, M. Valiev, D. Wang, E. Apra, T.L. Windus, J. Hammond, P. Nichols, S. Hirata, M.T. Hackler, Y. Zhao, P.-D. Fan, R.J. Harrison, M. Dupuis, D.M.A. Smith, J. Nieplocha, V. Tipparaju, M. Krishnan, Q. Wu, T. Van Voorhis, A.A. Auer, M. Nooijen, E. Brown, G. Cisneros, G.I. Fann, H. Fruchtl, J. Garza, K. Hirao, R. Kendall, J.A. Nichols, K. Tsemekhman, K. Wolinski, J. Anchell, D. Bernholdt, P. Borowski, T. Clark, D. Clerc, H. Dachsel, M. Deegan, K. Dyall, D. Elwood, E. Glendening, M. Gutowski, A. Hess, J. Jaffe, B. Johnson, J. Ju, R. Kobayashi, R. Kutteh, Z. Lin, R. Littlefield, X. Long, B. Meng, T. Nakajima, S. Niu, L. Pollack, M. Rosing, G. Sandrone, M. Stave, H. Taylor, G. Thomas, J. van Lenthe, A. Wong, Z. Zhang, NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.1 (Pacific Northwest National Laboratory, Richland, Washington, USA, 2007) Search in Google Scholar

[31] A.V. Luzanov, O.A. Zhikol, Int. J. Quant. Chem. 110, 902 (2010) Search in Google Scholar

[32] A.V. Luzanov, Russ. Chem. Rev. 49, 1033 (1980) http://dx.doi.org/10.1070/RC1980v049n11ABEH00252510.1070/RC1980v049n11ABEH002525Search in Google Scholar

[33] C. Reichardt, Chem. Rev. 94, 2319 (1994) http://dx.doi.org/10.1021/cr00032a00510.1021/cr00032a005Search in Google Scholar

[34] I.A.Z. Al-Ansari, J. Phys. Org. Chem. 10, 687 (1997) http://dx.doi.org/10.1002/(SICI)1099-1395(199709)10:9<687::AID-POC932>3.0.CO;2-A10.1002/(SICI)1099-1395(199709)10:9<687::AID-POC932>3.0.CO;2-ASearch in Google Scholar

[35] D. Yuan, R.G. Brown, J. Phys. Chem. A 101, 3461 (1997) http://dx.doi.org/10.1021/jp964061o10.1021/jp964061oSearch in Google Scholar

[36] A.B.J. Parusel, W. Nowak, S. Grimme, G. Köhler, J. Phys. Chem. A 102, 7149 (1998) http://dx.doi.org/10.1021/jp981540+10.1021/jp981540+Search in Google Scholar

[37] L. Biczók, T. Bérces, H. Inoue, J. Phys. Chem. A 103, 3837 (1999) http://dx.doi.org/10.1021/jp990208a10.1021/jp990208aSearch in Google Scholar

[38] F. Gao, H-R. Li, Y-y. Yang, Dyes Pigm. 47, 231 (2000) http://dx.doi.org/10.1016/S0143-7208(00)00052-810.1016/S0143-7208(00)00052-8Search in Google Scholar

[39] K. Rurack, J.L. Bricks, G. Reck, R. Radeglia, U. Resch-Genger, J. Phys. Chem. A 104, 3087 (2000) http://dx.doi.org/10.1021/jp994269k10.1021/jp994269kSearch in Google Scholar

[40] Z.R. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D.J. Cowley, W. Baumann, Nouv. J. Chim. 3, 443 (1979) Search in Google Scholar

[41] W. Rettig, Ang. Chem. Intl. Ed. Engl. 25, 971 (1986) http://dx.doi.org/10.1002/anie.19860971110.1002/anie.198609711Search in Google Scholar

[42] E. Lippert, W. Rettig, V. Bonacic-Koutecky, F. Heisel, J.A. Miehe, Adv. Chem. Phys. 68, 1 (1987) http://dx.doi.org/10.1002/9780470142967.ch110.1002/9780470142967.ch1Search in Google Scholar

[43] Z.R. Grabowski, K. Rotkiewicz, W. Rettig, Chem. Rev. 103, 3899 (2003) http://dx.doi.org/10.1021/cr940745l10.1021/cr940745lSearch in Google Scholar

[44] G. Wermuth, W. Rettig, E. Lippert, Ber. Bunsenges. phys. Chem. 85, 64 (1981) 10.1002/bbpc.19810850113Search in Google Scholar

[45] J. Herbich, J. Waluk, Chem. Phys. 188, 247 (1994) http://dx.doi.org/10.1016/0301-0104(94)00256-810.1016/0301-0104(94)00256-8Search in Google Scholar

[46] S. Mishina, S. Takayanagi, M. Nakata, J. Otsuki, K. Araki, J. Photochem. Photobiol. A: Chem. 141, 153 (2001) http://dx.doi.org/10.1016/S1010-6030(01)00456-710.1016/S1010-6030(01)00456-7Search in Google Scholar

[47] P. Avouris, W.M. Gelbart, M.A. El-Sayed, Chem. Rev. 77, 793–(1977) http://dx.doi.org/10.1021/cr60310a00210.1021/cr60310a002Search in Google Scholar

[48] R. Englman, J. Jortner, Mol. Phys. 18, 145 (1970) http://dx.doi.org/10.1080/0026897700010017110.1080/00268977000100171Search in Google Scholar

[49] W. Siebrand, J. Chem. Phys. 55, 5843 (1974) http://dx.doi.org/10.1063/1.167577010.1063/1.1675770Search in Google Scholar

[50] H. Fidder, M. Rini, E.T.J. Nibbering, J. Amer. Chem. Soc. 126, 3789 (2004) http://dx.doi.org/10.1021/ja038741y10.1021/ja038741ySearch in Google Scholar

[51] A.O. Doroshenko, M.D. Bilokin, V.G. Pivovarenko, J. Photochem. Photobiol. A: Chem. 163, 95 (2004) http://dx.doi.org/10.1016/S1010-6030(03)00435-010.1016/S1010-6030(03)00435-0Search in Google Scholar

[52] R.J. Willemse, D. Theodori, J.W. Verhoeven, A.M. Brouwer, Photochem. Photobiol. Sci. 2, 1134 (2003) http://dx.doi.org/10.1039/b307726h10.1039/B307726HSearch in Google Scholar

[53] A.O. Doroshenko, V.G. Pivovarenko, J. Photochem. Photobiol. A: Chem. 156, 55 (2003) http://dx.doi.org/10.1016/S1010-6030(03)00006-610.1016/S1010-6030(03)00006-6Search in Google Scholar

[54] A. Dreuw, M. Head-Gordon, Chem. Rev. 105, 4009 (2005) http://dx.doi.org/10.1021/cr050562710.1021/cr0505627Search in Google Scholar PubMed

[55] Y. Zhao, D.G. Truhlar, Chem. Phys. Lett. 502, 1 (2011) http://dx.doi.org/10.1016/j.cplett.2010.11.06010.1016/j.cplett.2010.11.060Search in Google Scholar

[56] X. Liu, D. Yang, H. Ju, F. Teng, Y. Hou, Z. Lou, Chem. Phys. Lett. 503, 75 (2011) http://dx.doi.org/10.1016/j.cplett.2011.01.00310.1016/j.cplett.2011.01.003Search in Google Scholar

[57] C-C. Yang, C-J. Hsu, P-T. Chou, H.C. Cheng, Y.O. Su, M-K. Leung, J. Phys. Chem. B 114, 756 (2010) http://dx.doi.org/10.1021/jp909306310.1021/jp9093063Search in Google Scholar PubMed

Published Online: 2011-9-27
Published in Print: 2011-12-1

© 2011 Versita Warsaw

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

Scroll Up Arrow