Artículo

Szalai, A.; Giordano, L.; Sánchez, V.M.; Atvars, T.D.Z.; Faleiros, M.; Jares-Erijman, E.; Aramendía, P.F."Temperature dependent spectroscopic and excited state dynamics of 3-hydroxychromones with electron donor and acceptor substituents" (2017) Methods and Applications in Fluorescence. 5(2)
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

We have studied the photophysical and photochemical behavior of three compounds derived from 3-hydroxychromone (3-HC), capable of undergoing excited state proton transfer (ESIPT). The compounds have two substituents, located in positions 2 and 7, one on each ring of the 3-HC heterocycle. The substituent pattern shows different electron donating and acceptor features. The compounds were studied by absorption and emission spectroscopy, steady state anisotropy, and time resolved emission spectroscopy (TRES) as a function of temperature. Results were interpreted using time dependent density functional theory calculations. Compared to reference compounds of 3-HC substituted only in the 2 position, the compounds show similar absorption and emission spectra, shifted 20-30 nm to higher wavelengths due to extended conjugation. TRES shows the existence of ESIPT in the thermodynamic equilibrium regime. This process is endothermic in all three compounds. The different behavior compared to monosubstituted 3-HC is attributed to the extended conjugation and to the electron donor acceptor character of the substituents, which has a more pronounced effect when the electron acceptor is located in position 2. © 2017 IOP Publishing Ltd.

Registro:

Documento: Artículo
Título:Temperature dependent spectroscopic and excited state dynamics of 3-hydroxychromones with electron donor and acceptor substituents
Autor:Szalai, A.; Giordano, L.; Sánchez, V.M.; Atvars, T.D.Z.; Faleiros, M.; Jares-Erijman, E.; Aramendía, P.F.
Filiación:Centro de Investigaciones en Bionanociencias 'Elizabeth Jares-Erijman' CIBION, CONICET, Godoy Cruz 2390, Ciudad de Buenos Aires, 1425, Argentina
Departamento de Química Inorgánica, Analítica y Química Física, FCEN, UBA, Ciudad Universitaria, Pabellón 2, Ciudad de Buenos Aires, 1428, Argentina
Departamento de Química Orgánica, FCEN, UBA, Ciudad Universitaria, Pabellón 2, Ciudad de Buenos Aires, 1428, Argentina
Centro de Simulación Computacional para Aplicaciones Tecnológicas, CSC-CONICET, Godoy Cruz 2390, Ciudad de Buenos Aires, 1425, Argentina
Chemistry Institute, University of Campinas, PO Box 6154, Campinas, SP, Brazil
CIHIDECAR-CONICET, Ciudad Universitaria, Pabellón 2, Ciudad de Buenos Aires, 1428, Argentina
Palabras clave:Anisotropy; ESIPT; Fluorescence; Ratiometric probe; TDDFT; Time resolved emission spectroscopy
Año:2017
Volumen:5
Número:2
DOI: http://dx.doi.org/10.1088/2050-6120/aa6ec0
Handle:http://hdl.handle.net/20.500.12110/paper_20506120_v5_n2_p_Szalai
Título revista:Methods and Applications in Fluorescence
Título revista abreviado:Methods Appl. Fluoresc.
ISSN:20506120
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20506120_v5_n2_p_Szalai

Referencias:

  • Klymchenko, A.S., Demchenko, A., Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer (2003) Phys. Chem. Chem. Phys., 5, pp. 461-468
  • Zhao, J., Ji, S., Chen, Y., Guo, H., Yang, P., Excited state intramolecular proton transfer (ESIPT): From principal photophysics to the development of new chromophores and applications in fluorescent molecular probes and luminescent materials (2012) Phys. Chem. Chem. Phys., 14, pp. 8803-8817
  • Yushchenko, D.A., Fauerbach, J.A., Thirunavukkuarasu, S., Jares-Erijman, E.A., Jovin, T.M., Fluorescent ratiometric MFC probe sensitive to early stages of alpha-synuclein aggregation (2010) J. Am. Chem. Soc., 132, pp. 7860-7861
  • Shynkar, V.V., Klymchenko, A.S., Kunzelmann, C., Duportail, G., Muller, C.D., Demchenko, A.P., Freyssinet, J.M., Mely, Y., Fluorescent biomembrane probe for ratiometric detection of apoptosis (2007) J. Am. Chem. Soc., 129, pp. 2187-2193
  • Kwon, J.E., Park, S.Y., Advanced organic optoelectronic materials: Harnessing excited-state intramolecular proton transfer (ESIPT) (2011) Process. Adv. Mater., 23, pp. 3615-3642
  • Sengupta, P.K., Kasha, M., Excited state proton-transfer spectroscopy of 3-hytdroxyflavone and quercetin (1979) Chem. Phys. Lett., 68, pp. 382-385
  • Tomin, V.I., Demchenko, A.P., Chou, P.-T., Thermodynamic versus kinetic control of excited-state proton transfer reactions (2015) J. Photochem. Photobiol. C, 22, pp. 1-18
  • Demchenko, A.P., Tang, K.C., Chou, P.-T., Excited-state proton coupled charge transfer modulated by molecular structure and media polarization (2013) Chem. Soc. Rev., 42, pp. 1379-1408
  • Schwartz, B.J., Peteanu, L.A., Harris, C.B., Direct observation of fast proton transfer: Femtosecond photophysics of 3-hydroxyflavone (1992) J. Phys. Chem., 96, pp. 3591-3598
  • Tomin, V.I., Oncul, S., Smolarczyk, G., Demchenko, A.P., Dynamic quenching as a simple test for the mechanism of excited-state reaction (2007) Chem. Phys., 342, pp. 126-134
  • Ghosh, D., Batuta, S., Das, S., Begum, N.A., Mandal, D., Proton transfer dynamics of 4′-N,N-dimethylamino-3-hydroxyflavone observed in hydrogen-bonding solvents and aqueous micelles (2015) J. Phys. Chem. B, 119, pp. 5650-5661
  • Dereka, B., Letrun, R., Svechkarev, D., Rosspeintner, A., Vauthey, E., Excited-state dynamics of 3-hydroxyflavone anion in alcohols (2015) J. Phys. Chem. B, 119, pp. 2434-2443
  • Roshal, A.D., Organero, J.A., Douhal, A., Tuning the mechanism of proton-transfer in a hydroxyflavone derivative (2003) Chem. Phys. Lett., 379, pp. 53-59
  • Shynkar, V.V., Mély, Y., Duportail, G., Piémont, E., Klymchenko, A.S., Demchenko, A.P., Picosecond time-resolved fluorescence studies are consistent with reversible excited-state intramolecular proton transfer in 4′-(Dialkylamino)-3-hydroxyflavones (2003) J. Phys. Chem. A, 107, pp. 9522-9529
  • Zhang, W., Shia, B., Shi, J., Time-dependent density functional investigation on electronic spectra of 4′-N-dimethylamino-3-hydroxyflavone (2005) J. Mol. Struct.: THEOCHEM, 731, pp. 219-224
  • Kenfack, C.A., Klymchenko, A.S., Duportail, G., Burger, A., Mély, Y., Ab initio study of the solvent H-bonding effect on ESIPT reaction and electronic transitions of 3-hydroxychromone derivatives (2012) Phys. Chem. Chem. Phys., 14, pp. 8910-8918
  • Klymchenko, A.S., Pivovarenko, V.G., Ozturk, T., Demchenko, A.P., Modulation of the solvent-dependent dual emission in 3-hydroxychromones by substituents (2003) New J. Chem., 27, pp. 1336-1343
  • Strandjord, A.J.G., Barbara, P.F., The proton-transfer kinetics of 3-hydroxyflavone: Solvent effects (1985) J. Phys. Chem., 89, pp. 2355-2361
  • Chou, P.-T., Pu, S.-C., Cheng, Y.-M., Yu, W.-S., Yu, Y.-C., Hung, F.-T., Hu, W.-P., Femtosecond dynamics on excited-state proton/charge-transfer reaction in 4′-N,Ndiethylamino-3-hydroxyflavone the role of dipolar vectors in constructing a rational mechanism (2005) J. Phys. Chem. A, 109, pp. 3777-3787
  • Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A., Jovin, T.M., Highly solvatochromic 7-Aryl-3-hydroxychromones (2012) J. Phys. Chem. Lett., 3, pp. 1011-1016
  • M'Baye, G., Klymchenko, A.S., Yushchenko, D.A., Shvadchak, V.V., Ozturk, T., Mely, Y., Duportail, G., Fluorescent dyes undergoing intramolecular proton transfer with improved sensitivity to surface charge in lipid bilayers (2007) Photochem. Photobiol. Sci., 6, pp. 71-76
  • Klymchenko, A.S., Mély, Y., 7-(2-Methoxycarbonylvinyl)-3-hydroxychromones: New dyes with red shifted dual emission (2004) Tetrahedron Lett., 45, pp. 8391-8394
  • Klymchenko, A.S., Yushchenko, D.A., Mely, Y., Tuning excited state intramolecular proton transfer in 3-hydroxyflavone derivative by reaction of its isothiocyanate group with an amine (2007) J. Photochem. Photobiol. A, 192, pp. 93-97
  • Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A., Jovin, T.M., Environment-sensitive Fluorophore Based on 2-Aryl-7-aryl-3-hydroxychromone, , to be published
  • Ehrhardt, C., McQuire, L.W., Rigollier, P., Rogel, O., Shultz, M., Tommasi, R.A., Arylsulfonamide-Based Matrix Metalloprotease Inhibitor (2009), 136p. https://register.epo.org/espacenet/regviewer?AP=09724483&CY=EP&LG=en&DB=REG, PCT Int. Appl.WO; Klymchenko, A.S., Mely, Y., 7-(2-Methoxycarbonylvinyl)-3-hydroxychromones: New dyes with red shifted dual emission (2004) Tetrahedron Lett., 45, pp. 8391-8394
  • Frisch, M.J., (2009) Gaussian 09, , http://gaussian.com/g09_b01, Revision B01, (Wallingford CT: Gaussian, Inc.)
  • Yanai, T., Tew, D.P., Handy, N.C., A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP) (2004) Chem. Phys. Lett., 393, pp. 51-57
  • Adamo, C., Jacquemin, D., The calculations of excited-state properties with time-dependent density functional theory (2013) Chem. Soc. Rev., 42, pp. 845-856
  • Tomasi, J., Persico, M., Molecular interactions in solution: An overview of methods based on continuous distributions of the solvent (1994) Chem. Rev., 94, pp. 2027-2094
  • Barone, V., Cossi, M., Tomasi, J., A new definition of cavities for the computation of solvation free energies by the polarizable continuum model (1997) J. Chem. Phys., 107, pp. 3210-3221
  • Improta, R., Barone, V., Scalmani, G., Frisch, M.J., A state-specific polarizable continuum model time dependent density functional theory method for excited state calculations in solution (2006) J. Chem. Phys., 125, p. 054103
  • Gunduz, S., Goren, A.C., Ozturk, T., Facile syntheses of 3-hydroxyflavones (2012) Org. Lett., 14, pp. 1576-1579
  • Cortés, J., Heitele, H., Jortner, J.J., Band-shape analysis of the charge-transfer fluorescence in barrelene-based electron donor-acceptor compounds (1994) J. Phys. Chem., 98, pp. 2527-2536
  • Tseng, H.-W., Shen, J.-Y., Kuo, T.-Y., Tu, T.-S., Chen, Y.-A., Demchenko, A.P., Chou, P.-T., Excited-state intramolecular proton-transfer reaction demonstrating anti-Kasha behavior (2016) Chem. Sci., 7, pp. 655-665
  • Oncul, S., Demchenko, A.P., The effects of thermal quenching on the excited-state intramolecular proton transfer reaction in 3-hydroxyflavones (2006) Spectrochim. Acta A, 65, pp. 179-183
  • Das, R., Klymchenko, A.S., Duportail, G., Mély, Y., Unusually slow proton transfer dynamics of a 3-hydroxychromone dye in protic solvents (2009) Photochem. Photobiol. Sci., 8, pp. 1583-1589

Citas:

---------- APA ----------
Szalai, A., Giordano, L., Sánchez, V.M., Atvars, T.D.Z., Faleiros, M., Jares-Erijman, E. & Aramendía, P.F. (2017) . Temperature dependent spectroscopic and excited state dynamics of 3-hydroxychromones with electron donor and acceptor substituents. Methods and Applications in Fluorescence, 5(2).
http://dx.doi.org/10.1088/2050-6120/aa6ec0
---------- CHICAGO ----------
Szalai, A., Giordano, L., Sánchez, V.M., Atvars, T.D.Z., Faleiros, M., Jares-Erijman, E., et al. "Temperature dependent spectroscopic and excited state dynamics of 3-hydroxychromones with electron donor and acceptor substituents" . Methods and Applications in Fluorescence 5, no. 2 (2017).
http://dx.doi.org/10.1088/2050-6120/aa6ec0
---------- MLA ----------
Szalai, A., Giordano, L., Sánchez, V.M., Atvars, T.D.Z., Faleiros, M., Jares-Erijman, E., et al. "Temperature dependent spectroscopic and excited state dynamics of 3-hydroxychromones with electron donor and acceptor substituents" . Methods and Applications in Fluorescence, vol. 5, no. 2, 2017.
http://dx.doi.org/10.1088/2050-6120/aa6ec0
---------- VANCOUVER ----------
Szalai, A., Giordano, L., Sánchez, V.M., Atvars, T.D.Z., Faleiros, M., Jares-Erijman, E., et al. Temperature dependent spectroscopic and excited state dynamics of 3-hydroxychromones with electron donor and acceptor substituents. Methods Appl. Fluoresc. 2017;5(2).
http://dx.doi.org/10.1088/2050-6120/aa6ec0