Photokinetics of two novel photochromic diarylethenes derived from benzothiophene

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- benzoth...

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Autores principales: Vázquez, A., Nudelman, N.S.
Formato: JOUR
Materias:
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
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_05388066_v44_n11_p736_Vazquez
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_05388066_v44_n11_p736_Vazquez2023-10-03T15:34:14Z Photokinetics of two novel photochromic diarylethenes derived from benzothiophene Vázquez, A. Nudelman, N.S. 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 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. Fil:Vázquez, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_05388066_v44_n11_p736_Vazquez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 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
spellingShingle 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
Vázquez, A.
Nudelman, N.S.
Photokinetics of two novel photochromic diarylethenes derived from benzothiophene
topic_facet 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
description 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.
format JOUR
author Vázquez, A.
Nudelman, N.S.
author_facet Vázquez, A.
Nudelman, N.S.
author_sort Vázquez, A.
title Photokinetics of two novel photochromic diarylethenes derived from benzothiophene
title_short Photokinetics of two novel photochromic diarylethenes derived from benzothiophene
title_full Photokinetics of two novel photochromic diarylethenes derived from benzothiophene
title_fullStr Photokinetics of two novel photochromic diarylethenes derived from benzothiophene
title_full_unstemmed Photokinetics of two novel photochromic diarylethenes derived from benzothiophene
title_sort photokinetics of two novel photochromic diarylethenes derived from benzothiophene
url http://hdl.handle.net/20.500.12110/paper_05388066_v44_n11_p736_Vazquez
work_keys_str_mv AT vazqueza photokineticsoftwonovelphotochromicdiarylethenesderivedfrombenzothiophene
AT nudelmanns photokineticsoftwonovelphotochromicdiarylethenesderivedfrombenzothiophene
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