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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paper:paper_05388066_v44_n11_p736_Vazquez2023-06-08T15:41:15Z Photokinetics of two novel photochromic diarylethenes derived from benzothiophene Vázquez, Alvaro Joaquín 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. 2012 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_05388066_v44_n11_p736_Vazquez 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, Alvaro Joaquín 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. |
author |
Vázquez, Alvaro Joaquín |
author_facet |
Vázquez, Alvaro Joaquín |
author_sort |
Vázquez, Alvaro Joaquín |
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 |
publishDate |
2012 |
url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_05388066_v44_n11_p736_Vazquez http://hdl.handle.net/20.500.12110/paper_05388066_v44_n11_p736_Vazquez |
work_keys_str_mv |
AT vazquezalvarojoaquin photokineticsoftwonovelphotochromicdiarylethenesderivedfrombenzothiophene |
_version_ |
1768546679235018752 |