Artículo
Abstract:
Two new unsymmetrically substituted photochromic diarylethenes, namely 3-[3, 3,4,4,5,5-hexafluoro-2-(2-methylbenzothien-3-yl)cyclopent-1-en-1-yl]-2- methyl-6-methoxy-1- benzothiophene and 3-[3,3,4,4,5,5-hexafluoro-2-(2- methylbenzothien-3-yl)cyclopent-1-en-1-yl]-2-methyl-6-methoxy-7-nitro-1- benzothiophene, were synthesized. Their optical properties and kinetics of cyclization and cycloreversion were determined in four solvents and compared with the symmetrical diarylethene (3,3,4,4,5,5-hexafluorocyclopent-1-en-1,2- diyl)bis(2-methyl-1-benzothiophene). While the UV spectra of the three compounds are almost insensitive to solvent changes, the rates of the ring-opening and ring-closure reactions exhibit interesting kinetic behavior that differs from other diarylethenes reported in the literature. The cycloreversion for the three compounds follows first-order kinetics, whereas the cyclization cannot be described by a simple kinetic law. Different approaches were tested, and a complex exponential equation could be derived that fits the experimental data. The unusual presence of two ring-opened conformational isomers, one of them nonphotochromic, is proposed for the ring-opened compounds to explain the derived kinetic law and observed solvent effects. These results are of interest in relation to the application of the novel diarylethenes as potential optical materials. © 2012 Wiley Periodicals, Inc.
Registro:
| Documento: | Artículo |
| Título: | Photokinetics of two novel photochromic diarylethenes derived from benzothiophene |
| Autor: | Vázquez, A.; Nudelman, N.S. |
| Filiación: | Departament of Organic Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EHA Buenos Aires, Argentina |
| Palabras clave: | Benzothiophene; Conformational isomers; Cycloreversion; Diarylethenes; Exponential equations; First order kinetics; Kinetic behavior; Kinetic law; Photochromic diarylethenes; Photokinetics; Ring opening; Ring-closure; Solvent effects; UV spectrum; Cyclization; Isomers; Olefins; Optical properties; Thiophene; Ultraviolet spectroscopy; Kinetics |
| Año: | 2012 |
| Volumen: | 44 |
| Número: | 11 |
| Página de inicio: | 736 |
| Página de fin: | 744 |
| DOI: | http://dx.doi.org/10.1002/kin.20727 |
| Título revista: | International Journal of Chemical Kinetics |
| Título revista abreviado: | Int J Chem Kinet |
| ISSN: | 05388066 |
| CODEN: | IJCKB |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_05388066_v44_n11_p736_Vazquez |
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Citas:
---------- APA ----------
Vázquez, A. & Nudelman, N.S. (2012) . Photokinetics of two novel photochromic diarylethenes derived from benzothiophene. International Journal of Chemical Kinetics, 44(11), 736-744.http://dx.doi.org/10.1002/kin.20727
---------- CHICAGO ----------
Vázquez, A., Nudelman, N.S. "Photokinetics of two novel photochromic diarylethenes derived from benzothiophene" . International Journal of Chemical Kinetics 44, no. 11 (2012) : 736-744.http://dx.doi.org/10.1002/kin.20727
---------- MLA ----------
Vázquez, A., Nudelman, N.S. "Photokinetics of two novel photochromic diarylethenes derived from benzothiophene" . International Journal of Chemical Kinetics, vol. 44, no. 11, 2012, pp. 736-744.http://dx.doi.org/10.1002/kin.20727
---------- VANCOUVER ----------
Vázquez, A., Nudelman, N.S. Photokinetics of two novel photochromic diarylethenes derived from benzothiophene. Int J Chem Kinet. 2012;44(11):736-744.http://dx.doi.org/10.1002/kin.20727
