Artículo

Montenegro, H.; Di Paolo, M.; Capdevila, D.; Aramendía, P.F.; Bossi, M.L. "The mechanism of the photochromic transformation of spirorhodamines" (2012) Photochemical and Photobiological Sciences. 11(6):1081-1086
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Abstract:

We investigate the equilibrium, kinetics, and mechanism of the photochromic transformation of a series of amido spirorhodamine compounds - differing in the nature of the substituents of the amido group and in the rhodamine chromophore - in ethanol at room temperature in the presence of trifluoroacetic acid. A proton participates in the equilibrium between the spiro form and the open rhodamine form. The relaxation times in the dark or under continuous irradiation show a linear dependence on the proton concentration. The slopes of these plots show a linear free energy relation with the equilibrium constant of the transformation. A mechanism involving reversible reaction steps between four states: the two thermodynamically stable isomers, a protonated spiro form, and a deprotonated open form, can account for the kinetic observations in the dark and under irradiation. © The Royal Society of Chemistry and Owner Societies 2012.

Registro:

Documento: Artículo
Título:The mechanism of the photochromic transformation of spirorhodamines
Autor:Montenegro, H.; Di Paolo, M.; Capdevila, D.; Aramendía, P.F.; Bossi, M.L.
Filiación:Departamento de Química Inorgánica, Analítica y Química Física, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Año:2012
Volumen:11
Número:6
Página de inicio:1081
Página de fin:1086
DOI: http://dx.doi.org/10.1039/c2pp05402g
Título revista:Photochemical and Photobiological Sciences
Título revista abreviado:Photochem. Photobiol. Sci.
ISSN:1474905X
CODEN:PPSHC
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v11_n6_p1081_Montenegro

Referencias:

  • (1990) Photochromism. Molecules and Systems, , ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam
  • (1999) Organic Photochromic and Thermochromic Compounds, , ed. J. C. Crano and R. J. Guglielmetti, Plenum Press, New York
  • Photochromism. Molecules and switches (2000) Thematic Issue. Chem. Rev., 100 (5)
  • Favaro, G., Irie, M., Special issue on photochromism (2011) J. Photochem. Photobiol., C: Photochem. Rev., 12, pp. 71-236
  • Natansohn, A., Rochon, P., Photoinduced motions in azo-containing polymers (2002) Chem. Rev., 102, pp. 4139-4175
  • Ichimura, K., Photoalignment of liquid-crystal systems (2000) Chem. Rev., 100, pp. 1847-1874
  • Yamada, M., Kondo, M., Mamiya, J., Yu, Y., Kinoshita, M., Barrett, C.J., Ikeda, T., Photomobile polymer materials: Towards light driven plastic motors (2008) Angew. Chem., Int. Ed., 47, pp. 4986-4988
  • Davis, D.A., Hamilton, A., Yang, J., Cremar, L.D., Van Gough, D., Potisek, S.L., Ong, M.T., Sottos, N.R., Force-induced activation of covalent bonds in mechanoresponsive polymeric materials (2009) Nature, 459, pp. 68-72
  • Hell, S.W., Toward fluorescence nanoscopy (2003) Nat. Biotechnol., 21, pp. 1347-1355
  • Hell, S.W., Far-field optical nanoscopy (2007) Science, 316, pp. 1153-1158
  • Hell, S.W., Microscopy and its focal switch (2009) Nat. Methods, 6, pp. 24-32
  • Knauer, K.-H., Gleiter, R., Photochromism of rhodarnine derivatives (1977) Angew. Chem., Int. Ed. Engl., 16, p. 113
  • Fölling, J., Belov, V., Kunetsky, R., Medda, R., Schönle, A., Egner, A., Eggeling, C., Hell, S.W., Photochromic rhodamines provide nanoscopy with optical sectioning (2007) Angew. Chem., Int. Ed., 46, pp. 6266-6270
  • Fölling, J., Belov, V., Riedel, D., Schönle, A., Egner, A., Eggeling, C., Bossi, M., Hell, S.W., Fluorescence nanoscopy with optical sectioning by two-photon induced molecular switching using continuous-wave lasers (2008) ChemPhysChem, 9, pp. 321-326
  • Karstens, T., Kobs, K., Rhodamine B and rhodamine 101 as reference substances for fluorescence quantum yield measurements (1980) J. Phys. Chem., 84, pp. 1871-1872
  • Magde, D., Rojas, G.E., Seybold, P.G., Solvent dependence of the fluorescence lifetimes of xanthene dyes (1999) Photochem. Photobiol., 70, pp. 737-744
  • Willwohl, H., Wolfrum, J., Gleiter, R., Kinetics and mechanism of the photochromism of N-phenyl-rhodaminelactame (1989) Laser Chem., 10, pp. 63-72
  • Bossi, M., Fölling, J., Belov, V.N., Boyarskiy, V.P., Medda, R., Egner, A., Eggeling, C., Hell, S.W., Multicolor far-field fluorescence nanoscopy through isolated detection of distinct molecular species (2008) Nano Lett., 8, pp. 2463-2468
  • Testa, I., Schönle, A., Middendorff, C.V., Geisler, C., Medda, R., Wurm, C.A., Stiel, A.C., Egner, A., Nanoscale separation of molecular species based on their rotational mobility (2008) Opt. Express, (16), pp. 21093-21104
  • Belov, V.N., Bossi, M.L., Fölling, J., Boyarskiy, V.P., Hell, S.W., Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy (2009) Chem.-Eur. J., 15, pp. 10762-10776
  • Adamczyk, M., Grote, J., Efficient synthesis of rhodamine conjugates through the 2′-position (2000) Bioorg. Med. Chem. Lett., 10, pp. 1539-1541
  • Adamczyk, M., Grote, J., Synthesis of novel spirolactams by reaction of fluorescein methyl ester with amines (2000) Tetrahedron Lett., 41, pp. 807-809
  • Adamczyk, M., Grote, J., Synthesis of probes with broad pH range fluorescence (2003) Bioorg. Med. Chem. Lett., 13, pp. 2327-2330
  • Wojtyk, J.T.C., Wasey, A., Xiao, N.-N., Kazmaier, P.M., Hoz, S., Yu, C., Lemieux, R.P., Buncel, E., Elucidating the mechanisms of acidochromic spiropyran-merocyanine interconversion (2007) J. Phys. Chem. A, 111, pp. 2511-2516
  • Best, Q.A., Xu, R., McCarroll, M.E., Wang, L., Dyer, D.J., Design and investigation of a series of rhodamine-based fluorescent probes for optical measurements of pH (2010) Org. Lett., 12, pp. 3219-3221
  • Chen, X., Pradhan, T., Wang, F., Kim, J.S., Yoon, J., Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives (2012) Chem. Rev., 112 (3), pp. 1910-1956

Citas:

---------- APA ----------
Montenegro, H., Di Paolo, M., Capdevila, D., Aramendía, P.F. & Bossi, M.L. (2012) . The mechanism of the photochromic transformation of spirorhodamines. Photochemical and Photobiological Sciences, 11(6), 1081-1086.
http://dx.doi.org/10.1039/c2pp05402g
---------- CHICAGO ----------
Montenegro, H., Di Paolo, M., Capdevila, D., Aramendía, P.F., Bossi, M.L. "The mechanism of the photochromic transformation of spirorhodamines" . Photochemical and Photobiological Sciences 11, no. 6 (2012) : 1081-1086.
http://dx.doi.org/10.1039/c2pp05402g
---------- MLA ----------
Montenegro, H., Di Paolo, M., Capdevila, D., Aramendía, P.F., Bossi, M.L. "The mechanism of the photochromic transformation of spirorhodamines" . Photochemical and Photobiological Sciences, vol. 11, no. 6, 2012, pp. 1081-1086.
http://dx.doi.org/10.1039/c2pp05402g
---------- VANCOUVER ----------
Montenegro, H., Di Paolo, M., Capdevila, D., Aramendía, P.F., Bossi, M.L. The mechanism of the photochromic transformation of spirorhodamines. Photochem. Photobiol. Sci. 2012;11(6):1081-1086.
http://dx.doi.org/10.1039/c2pp05402g