Síntesis de dímeros fotoactivos con unidad central de 1,3,4-Tiadiazol.
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Date
2022
Journal Title
Journal ISSN
Volume Title
Publisher
Universidad de Concepción
Abstract
En la actualidad existe una constante búsqueda de nuevos materiales y los materiales moleculares han sido foco de investigación por años. De interés son los materiales fotoactivos que incluyen grupos como cianobifenilo y azobenceno y los cristales líquidos, que presentan un estado intermedio entre sólido y líquido, y se ven favorecidos por la incorporación de heterociclos como 1,3,4-tiadiazol a las moléculas. En este trabajo de tesis, se sintetizaron cinco nuevos compuestos finales derivados de 1,3,4-tiadiazol organizados en dos series que incorporan unidades fotoactivas de cianobifenilo y azobenceno, teniendo la serie I como conexión al centro rígido un grupo éster y la serie II un grupo éter. Estos compuestos fueron caracterizados por espectroscopía infrarroja y resonancia magnética nuclear de 1H y 13C y se determinaron sus propiedades térmicas y mesomorfas por microscopía óptica de luz polarizada y análisis termogravimétrico. Finalmente, se estudiaron sus propiedades optoelectrónicas mediante el estudio de fotoisomerización para los grupos azo y fluorescencia para los grupos cianobifenilo. Los compuestos de ambas series presentaron propiedades cristal líquido de tipo termótropo enantiótropo con amplios rangos mesomorfos y la fotoactividad característica de cada grupo.
Currently, there is a constant search for new materials, and molecular materials have been the focus of research for years. Of interest are photoactive materials, which include groups such as cyanobiphenyl and azobenzene; and liquid crystals, which present an intermediate state between solid and liquid, and are favored by the incorporation of heterocycles such as 1,3,4-thiadiazole to the molecules. In this thesis work, five new final compounds derived from 1,3,4-thiadiazole were synthesized, organized in two series incorporating cyanobiphenyl and azobenzene photoactive units, with series I having as connection to the rigid center an ester group and series II an ether group. These compounds were characterized by infrared spectroscopy and NMR 1H and 13C, and their thermal and mesomorphic properties were determined by polarized light optical microscopy and thermogravimetric analysis. Finally, their optoelectronic properties were studied by photoisomerization study for azo groups and fluorescence for cyanobiphenyl groups. The compounds of both series exhibited enantiotropic thermotropic-type liquid crystal properties with wide mesomorphic ranges, and the characteristic photoactivity of each group.
Currently, there is a constant search for new materials, and molecular materials have been the focus of research for years. Of interest are photoactive materials, which include groups such as cyanobiphenyl and azobenzene; and liquid crystals, which present an intermediate state between solid and liquid, and are favored by the incorporation of heterocycles such as 1,3,4-thiadiazole to the molecules. In this thesis work, five new final compounds derived from 1,3,4-thiadiazole were synthesized, organized in two series incorporating cyanobiphenyl and azobenzene photoactive units, with series I having as connection to the rigid center an ester group and series II an ether group. These compounds were characterized by infrared spectroscopy and NMR 1H and 13C, and their thermal and mesomorphic properties were determined by polarized light optical microscopy and thermogravimetric analysis. Finally, their optoelectronic properties were studied by photoisomerization study for azo groups and fluorescence for cyanobiphenyl groups. The compounds of both series exhibited enantiotropic thermotropic-type liquid crystal properties with wide mesomorphic ranges, and the characteristic photoactivity of each group.
Description
Tesis presentada para optar al título de Bioquímico/a.
Keywords
Fluorescencia, Irradación, Isomerización, Resonancia Magnética