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Hršak, D.; Holmegaard, L.; Poulsen, A.S.; List, N.H.; Kongsted, J.; Denofrio, M.P.; Erra-Balsells, R.; Cabrerizo, F.M.; Christiansen, O.; Ogilby, P.R. "Experimental and computational study of solvent effects on one- and two-photon absorption spectra of chlorinated harmines" (2015) Physical Chemistry Chemical Physics. 17(18):12090-12099
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Abstract:

A combined experimental and computational study of solvent effects on one- and two-photon absorption spectra of three chlorinated harmine derivatives is presented. The systems studied were protonated forms of 6-chloroharmine, 8-chloroharmine and 6,8-dichloroharmine in two solvents, acetonitrile and water. For the computations, polarizable embedding density functional and coupled cluster response theory methods were used. The computations were able to model the solvent-dependent experimental data well. These results demonstrate that reasonably sophisticated computational methods can be successfully applied to accurately study linear and nonlinear spectroscopic properties of comparatively large organic molecules in solution. © the Owner Societies 2015.

Registro:

Documento: Artículo
Título:Experimental and computational study of solvent effects on one- and two-photon absorption spectra of chlorinated harmines
Autor:Hršak, D.; Holmegaard, L.; Poulsen, A.S.; List, N.H.; Kongsted, J.; Denofrio, M.P.; Erra-Balsells, R.; Cabrerizo, F.M.; Christiansen, O.; Ogilby, P.R.
Filiación:Center for Oxygen Microscopy and Imaging, Aarhus University, Langelandsgade 140, Aarhus C, 8000, Denmark
Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, Odense M, 5230, Denmark
Instituto de Investigaciones Biotecnológicas, Instituto Tecnológico de Chascomús (IIB-INTECH), Científicas y Técnicas (CONICET), Intendente Marino Km 8.2, CC 164, Chascomús, B7130IWA, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Buenos Aires, 1428, Argentina
Palabras clave:acetonitrile; acetonitrile derivative; harmine; psychedelic agent; solvent; water; analogs and derivatives; chemical structure; chemistry; computer simulation; conformation; halogenation; photon; spectrophotometry; Acetonitriles; Computer Simulation; Hallucinogens; Halogenation; Harmine; Models, Molecular; Molecular Conformation; Photons; Solvents; Spectrophotometry; Water
Año:2015
Volumen:17
Número:18
Página de inicio:12090
Página de fin:12099
DOI: http://dx.doi.org/10.1039/c5cp00773a
Título revista:Physical Chemistry Chemical Physics
Título revista abreviado:Phys. Chem. Chem. Phys.
ISSN:14639076
CODEN:PPCPF
CAS:acetonitrile, 75-05-8; harmine, 343-27-1, 442-51-3; water, 7732-18-5; acetonitrile; Acetonitriles; Hallucinogens; Harmine; Solvents; Water
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14639076_v17_n18_p12090_Hrsak

Referencias:

  • Pawlicki, M., Collins, H., Denning, R., Anderson, H., (2009) Angew. Chem., Int. Ed., 48, pp. 3244-3266
  • Terenziani, F., Katan, C., Badaeva, E., Tretiak, S., Blanchard-Desce, M., (2008) Adv. Mater., 20, pp. 4641-4678
  • Denk, W., Strickler, J., Webb, W., (1990) Science, 248, pp. 73-76
  • König, K., So, P.T.C., Mantulin, W.W., Tromberg, B.J., Gratton, E., (1996) J. Microsc., 183, pp. 197-204
  • Stellacci, F., Bauer, C., Meyer-Friedrichsen, T., Wenseleers, W., Alain, V., Kuebler, S., Pond, S., Perry, J., (2002) Adv. Mater., 14, pp. 194-198
  • McClain, W.M., (1971) J. Chem. Phys., 55, pp. 2789-2796
  • Hudson, B., Kohler, B., (1972) Chem. Phys. Lett., 14, pp. 299-304
  • Birge, R.R., (1986) Acc. Chem. Res., 19, pp. 138-146
  • Ogilby, P.R., (2010) Chem. Soc. Rev., 39, pp. 3181-3209
  • Albota, M., Beljonne, D., Brédas, J.-L., Ehrlich, J.E., Fu, J.-Y., Heikal, A.A., Hess, S.E., Xu, C., (1998) Science, 281, pp. 1653-1656
  • Xu, C., Webb, W.W., (1996) J. Opt. Soc. Am. B, 13, pp. 481-491
  • Arnbjerg, J., Johnsen, M., Frederiksen, P.K., Braslavsky, S.E., Ogilby, P.R., (2006) J. Phys. Chem. A, 110, pp. 7375-7385
  • Makarov, N.S., Drobizhev, M., Rebane, A., (2008) Opt. Express, 16, pp. 4029-4047
  • List, N.H., Pimenta, F.M., Holmegaard, L., Jensen, R.L., Etzerodt, M., Schwabe, T., Kongsted, J., Christiansen, O., (2014) Phys. Chem. Chem. Phys., 16, pp. 9950-9959
  • Drobizhev, M., Tillo, S., Makarov, N.S., Hughes, T.E., Rebane, A., (2009) J. Phys. Chem. B, 113, pp. 855-859
  • Kruk, M., Karotki, A., Drobizhev, M., Kuzmitsky, V., Gael, V., Rebane, A., (2003) J. Lumin., 105, pp. 45-55
  • Murugan, N.A., Kongsted, J., Rinkevicius, Z., Aidas, K., Mikkelsen, K.V., Ågren, H., (2011) Phys. Chem. Chem. Phys., 13, pp. 12506-12516
  • Wielgus, M., Zales̈ny, R., Murugan, N.A., Kongsted, J., Ågren, H., Samoc, M., Bartkowiak, W., (2013) ChemPhysChem, 14, pp. 3731-3739
  • Makarov, N.S., Mukhopadhyay, S., Yesudas, K., Brédas, J.-L., Perry, J.W., Pron, A., Kivala, M., Müllen, K., (2012) J. Phys. Chem. A, 116, pp. 3781-3793
  • Fedorov, I., Koziol, L., Mollner, A.K., Krylov, A.I., Reisler, H., (2009) J. Phys. Chem. A, 113, pp. 7412-7421
  • Arnbjerg, J., Paterson, M.J., Nielsen, C.B., Jørgensen, M., Christiansen, O., Ogilby, P.R., (2007) J. Phys. Chem. A, 111, pp. 5756-5767
  • Olsen, J., Jørgensen, P., (1985) J. Chem. Phys., 82, pp. 3235-3264
  • Christiansen, O., Jørgensen, P., Hättig, C., (1998) Int. J. Quantum Chem., 68, pp. 1-52
  • Runge, E., Gross, E.K.U., (1984) Phys. Rev. Lett., 52, pp. 997-1000
  • Johnsen, M., Ogilby, P.R., (2008) J. Phys. Chem. A, 112, pp. 7831-7839
  • Woo, H., Hong, J., Liu, B., Mikhailovsky, A., Korystov, D., Bazan, G., (2005) J. Am. Chem. Soc., 127, pp. 820-821
  • Wielgus, M., Bartkowiak, W., Samoc, M., (2012) Chem. Phys. Lett., 554, pp. 113-116
  • Wielgus, M., Michalska, J., Samoc, M., Bartkowiak, W., (2015) Dyes Pigm., 113, pp. 426-434
  • Wicks, G., Rebane, A., Drobizhev, M., (2014) Proc. SPIE, 8983, p. 89830R
  • Neto, N.B., Correa, D., Boni, L.D., Parra, G., Misoguti, L., Mendonça, C., Borissevitch, I., Gonçalves, P., (2013) Chem. Phys. Lett., 587, pp. 118-123
  • Terenziani, F., Painelli, A., Katan, C., Charlot, M., Blanchard-Desce, M., (2006) J. Am. Chem. Soc., 128, pp. 15742-15755
  • Blázquez-Castro, A., Breitenbach, T., Ogilby, P.R., (2014) Photochem. Photobiol. Sci., 13, pp. 1235-1240
  • Lamchouri, F., Settaf, A., Cherrah, Y., Hassar, M., Zemzami, M., Atif, N., Nadori, E., Lyoussi, B., (2000) Fitoterapia, 71, pp. 50-54
  • Vignoni, M., Erra-Balsells, R., Epe, B., Cabrerizo, F.M., (2014) J. Photochem. Photobiol., B, 132, pp. 66-71
  • Gonzalez, M.M., Arnbjerg, J., Denofrio, M.P., Erra-Balsells, R., Ogilby, P.R., Cabrerizo, F.M., (2009) J. Phys. Chem. A, 113, pp. 6648-6656
  • Olsen, J.M.H., Kongsted, J., (2011) Adv. Quantum Chem., 61, pp. 107-143
  • Olsen, J.M.H., Aidas, K., Kongsted, J., (2010) J. Chem. Theory Comput., 6, pp. 3721-3734
  • Schwabe, T., Sneskov, K., Olsen, J.M.H., Kongsted, J., Christiansen, O., Hättig, C., (2012) J. Chem. Theory Comput., 8, pp. 3274-3283
  • Sneskov, K., Schwabe, T., Kongsted, J., Christiansen, O., (2011) J. Chem. Phys., 134, p. 104108
  • Ponce, M.A., Tarzi, O.I., Erra-Balsells, R., (2003) J. Heterocycl. Chem., 40, pp. 419-426
  • Frederiksen, P.K., Jørgensen, M., Ogilby, P.R., (2001) J. Am. Chem. Soc., 123, pp. 1215-1221
  • Meech, S.R., Phillips, D., (1983) J. Photochem., 23, pp. 193-217
  • Kennedy, S.M., Lytle, F.E., (1986) Anal. Chem., 58, pp. 2643-2647
  • Fisher, W.G., Wachter, E.A., Lytle, F.E., Armas, M., Seaton, C., (1998) Appl. Spectrosc., 52, pp. 536-545
  • (2012) QSite, Version 5.8, , Schrödinger, LLC, New York, NY
  • Gagliardi, L., Lindh, R., Karlström, G., (2004) J. Chem. Phys., 121, pp. 4494-4500
  • Karlström, G., Lindh, R., Malmqvist P.-Å., Roos, B.O., Ryde, U., Veryazov, V., Widmark, P.-O., Seijo, L., (2003) Comput. Mater. Sci., 28, pp. 222-239
  • Aquilante, F., De Vico, L., Ferré, N., Ghigo, G., Malmqvist P.-Å., Neogrády, P., Pedersen, T.B., Lindh, R., (2010) J. Comput. Chem., 31, pp. 224-247
  • Olsen, J.M.H., (2012), PhD thesis, University of Southern Denmark, Odense, Denmark; Yanai, T., Tew, D.P., Handy, N.C., (2004) Chem. Phys. Lett., 393, pp. 51-57
  • Friese, D.H., Hättig, C., Ruud, K., (2012) Phys. Chem. Chem. Phys., 14, pp. 1175-1184
  • Dunning, T.H., (1989) J. Chem. Phys., 90, pp. 1007-1023
  • (2011) DALTON, A Molecular Electronic Structure Program, Release Dalton2011, , http://daltonprogram.org/, see
  • Aidas, K., Angeli, C., Bak, K.L., Bakken, V., Bast, R., Boman, L., Christiansen, O., Ågren, H., (2014) Wiley Interdiscip. Rev.: Comput. Mol. Sci., 4, pp. 269-284
  • http://www.turbomole.com, TURBOMOLE V6.4 2012, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007; available from; Lin, N., Luo, Y., Ruud, K., Zhao, X., Santoro, F., Rizzo, A., (2011) ChemPhysChem, 12, pp. 3392-3403
  • McClain, W.M., (1974) Acc. Chem. Res., 7, pp. 129-135
  • Nielsen, C.B., Arnbjerg, J., Johnsen, M., Jørgensen, M., Ogilby, P.R., (2009) J. Org. Chem., 74, pp. 9094-9104
  • List, N.H., Olsen, J.M.H., Rocha-Rinza, T., Christiansen, O., Kongsted, J., (2012) Int. J. Quantum Chem., 112, pp. 789-800
  • Schaftenaar, G., Noordik, J., (2000) J. Comput.-Aided Mol. Des., 14, pp. 123-134
  • Orr, B., Ward, J., (1971) Mol. Phys., 20, pp. 513-526
  • Birge, R.R., Pierce, B.M., (1979) J. Chem. Phys., 70, pp. 165-178
  • Dick, B., Hohlneicher, G., (1979) Theor. Chim. Acta, 53, pp. 221-251

Citas:

---------- APA ----------
Hršak, D., Holmegaard, L., Poulsen, A.S., List, N.H., Kongsted, J., Denofrio, M.P., Erra-Balsells, R.,..., Ogilby, P.R. (2015) . Experimental and computational study of solvent effects on one- and two-photon absorption spectra of chlorinated harmines. Physical Chemistry Chemical Physics, 17(18), 12090-12099.
http://dx.doi.org/10.1039/c5cp00773a
---------- CHICAGO ----------
Hršak, D., Holmegaard, L., Poulsen, A.S., List, N.H., Kongsted, J., Denofrio, M.P., et al. "Experimental and computational study of solvent effects on one- and two-photon absorption spectra of chlorinated harmines" . Physical Chemistry Chemical Physics 17, no. 18 (2015) : 12090-12099.
http://dx.doi.org/10.1039/c5cp00773a
---------- MLA ----------
Hršak, D., Holmegaard, L., Poulsen, A.S., List, N.H., Kongsted, J., Denofrio, M.P., et al. "Experimental and computational study of solvent effects on one- and two-photon absorption spectra of chlorinated harmines" . Physical Chemistry Chemical Physics, vol. 17, no. 18, 2015, pp. 12090-12099.
http://dx.doi.org/10.1039/c5cp00773a
---------- VANCOUVER ----------
Hršak, D., Holmegaard, L., Poulsen, A.S., List, N.H., Kongsted, J., Denofrio, M.P., et al. Experimental and computational study of solvent effects on one- and two-photon absorption spectra of chlorinated harmines. Phys. Chem. Chem. Phys. 2015;17(18):12090-12099.
http://dx.doi.org/10.1039/c5cp00773a