Abstract:
Solid niobium oxides (Nb2O5·nH2O) and niobium phosphate were used as heterogeneous acid catalysts to promote the condensation between a switchable oxazine and a fluorescent coumarin in an aprotic solvent. The catalysts were found to promote the generation of an active methylene from the enamine-based portion of the oxazine, which was followed by a nucleophilic attack on the aldehyde functionality of the coumarin reagent. In the resulting system, the emission of the conjugated fluorophore can be observed at 670 nm and, thus, the processes occurring at the catalyst surface can be monitored in real time by total internal reflection fluorescence microscopy (TIRFM). © The Royal Society of Chemistry 2015.
Registro:
Documento: |
Artículo
|
Título: | Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly |
Autor: | Impellizzeri, S.; Simoncelli, S.; Fasciani, C.; Marin, M.L.; Hallett-Tapley, G.L.; Hodgson, G.K.; Scaiano, J.C. |
Filiación: | Department of Chemistry, Centre for Catalysis Research and Innovation, University of Ottawa, 10 Marie Curie, Ottawa, ON K1N 6N5, Canada Departamento de Química Inorgánica, Analítica, Y Química Física, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Buenos Aires, 1428, Argentina Instituto Universitario Mixto de Tecnología Química (UPV-CSIC), Universitat Politècnica de València, Avenida de los Naranjos s/n, Valencia, 46022, Spain
|
Palabras clave: | Catalysts; Condensation; Fluorescence; Fluorescence microscopy; Fluorophores; Niobium; Nitrogen compounds; Refractive index; Aprotic solvents; Catalyst surfaces; Heterogeneous acid catalysts; In-situ condensations; Niobium phosphates; Nucleophilic attack; Switchable; Total internal reflection fluorescence microscopy; Niobium oxide |
Año: | 2015
|
Volumen: | 5
|
Número: | 1
|
Página de inicio: | 169
|
Página de fin: | 175
|
DOI: |
http://dx.doi.org/10.1039/c4cy00703d |
Título revista: | Catalysis Science and Technology
|
Título revista abreviado: | Catal. Sci. Technolog.
|
ISSN: | 20444753
|
CODEN: | CSTAG
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20444753_v5_n1_p169_Impellizzeri |
Referencias:
- Feringa, B.L., (2001) Molecular Switches, , Wiley-VCH, Weinheim
- Crano, J.C., Guglielmetti, R.J., (1999) Organic Photochromic and Thermochromic Compounds, , Plenum Press, New York
- Irie, M., (2000) Chem. Rev., 100, pp. 1683-1890
- Parthenopoulos, D.A., Rentzepis, P.M., (1989) Science, 245, pp. 843-845
- Dvornikov, A.S., Malkin, J., Rentzepis, P.M., (1994) J. Phys. Chem., 98, pp. 6746-6752
- Dvornikov, A.S., Walker, E.P., Rentzepis, P.M., (2009) J. Phys. Chem. A, 113, pp. 13633-13644
- De Silva, A.P., McClenaghan, N.D., McCoy, C.P., (2001) Electron Transfer in Chemistry, pp. 156-185. , ed. V. Balzani, Wiley-VCH, Weinheim
- Balzani, V., Credi, A., Venturi, M., (2008) Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld, , Wiley-VCH, Weinheim
- Raymo, F.M., Giordani, S., (2001) Org. Lett., 3, pp. 3475-3478
- Raymo, F.M., (2002) Adv. Mater., 14, pp. 401-414
- Raymo, F.M., Giordani, S., White, A.J.P., Williams, D.J., (2003) J. Org. Chem., 68, pp. 4158-4169
- Raymo, F.M., Alvarado, R.J., Giordani, S., Cejas, M.A., (2003) J. Am. Chem. Soc., 125, pp. 2361-2364
- Silvi, S., Constable, E.C., Housecroft, C.E., Beves, J.E., Dunphy, E.L., Tomasulo, M., Raymo, F.M., Credi, A., (2009) Chem. - Eur. J., 15, pp. 178-185
- Cusido, J., Impellizzeri, S., Raymo, F.M., (2011) Nanoscale, 3, pp. 59-70
- Raymo, F.M., (2012) J. Phys. Chem. Lett., 3, pp. 2379-2385
- Deniz, E., Tomasulo, M., Cusido, J., Yildiz, I., Petriella, M., Bossi, M.L., Sortino, S., Raymo, F.M., (2012) J. Phys. Chem. C, 116, pp. 6058-6068
- Petriella, M., Deniz, E., Swaminathan, S., Roberti, M.J., Raymo, F.M., Bossi, M.L., (2013) Photochem. Photobiol., 89, pp. 1391-1398
- Marin, M.L., Hallett-Tapley, G., Impellizzeri, S., Fasciani, C., Simoncelli, S., Netto-Ferreira, J.C., Scaiano, J.C., (2014) Catal. Sci. Technol., 4, pp. 3044-3052
- Nowak, I., Ziolek, M., (1999) Chem. Rev., 99, pp. 3603-3624
- Okazaki, S., Kurosaki, A., (1990) Catal. Today, 8, pp. 113-122
- Okazaki, S., Wada, N., (1993) Catal. Today, 16, pp. 349-359
- Ushikubo, T., Iizuka, I., Hattori, H., Tanabe, K., (1993) Catal. Today, 16, pp. 291-295
- Sun, Q., Auroux, A., Shen, J., (2006) J. Catal., 244, pp. 1-9
- Bassan, I.A.L., Nascimento, D.R., San Gil, R.A.S., Da Silva, M.I.P., Moreira, C.R., Gonzalez, W.A., Faro, A.C., Jr., Lachter, E.R., (2013) Fuel Process. Technol., 106, pp. 619-624
- Deniz, E., Sortino, S., Raymo, F.M., (2010) J. Phys. Chem. Lett., 1, pp. 3506-3509
- Tomasulo, M., Sortino, S., White, A.J.P., Raymo, F.M., (2005) J. Org. Chem., 70, pp. 8180-8189
- Wu, J.-S., Liu, W.-M., Zhuang, X.-Q., Wang, F., Wang, P.-F., Tao, S.-L., Zhang, X.-H., Lee, S.-T., (2006) Org. Lett., 9, pp. 33-36
- Matsuzaki, I., Nitta, M., Tanabe, K., (1969) J. Res. Inst. Catal., 17, pp. 46-53. , Hokkaido Univ
- Yurdakoc, M., Akcay, M., Tonbul, Y., Yurdakoc, K., (1999) Turk. J. Chem., 23, pp. 319-327
- Corma, A., Martinez, A., (1995) Adv. Mater., 7, pp. 137-144
- Corrent, S., Hahn, P., Pohlers, G., Connolly, T.J., Scaiano, J.C., Fornés, V., García, H., (1998) J. Phys. Chem. B, 102, pp. 5852-5858
- Scaiano, J.C., García, H., (1999) Acc. Chem. Res., 32, pp. 783-793
Citas:
---------- APA ----------
Impellizzeri, S., Simoncelli, S., Fasciani, C., Marin, M.L., Hallett-Tapley, G.L., Hodgson, G.K. & Scaiano, J.C.
(2015)
. Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly. Catalysis Science and Technology, 5(1), 169-175.
http://dx.doi.org/10.1039/c4cy00703d---------- CHICAGO ----------
Impellizzeri, S., Simoncelli, S., Fasciani, C., Marin, M.L., Hallett-Tapley, G.L., Hodgson, G.K., et al.
"Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly"
. Catalysis Science and Technology 5, no. 1
(2015) : 169-175.
http://dx.doi.org/10.1039/c4cy00703d---------- MLA ----------
Impellizzeri, S., Simoncelli, S., Fasciani, C., Marin, M.L., Hallett-Tapley, G.L., Hodgson, G.K., et al.
"Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly"
. Catalysis Science and Technology, vol. 5, no. 1, 2015, pp. 169-175.
http://dx.doi.org/10.1039/c4cy00703d---------- VANCOUVER ----------
Impellizzeri, S., Simoncelli, S., Fasciani, C., Marin, M.L., Hallett-Tapley, G.L., Hodgson, G.K., et al. Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly. Catal. Sci. Technolog. 2015;5(1):169-175.
http://dx.doi.org/10.1039/c4cy00703d