2005
DOI: 10.1107/s160053680503816x
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3,3,4,4,5,5-Hexafluoro-1-[2-methyl-5-(2-fluorophenyl)-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)cyclopent-1-ene, a new photochromic dithienylethene

Abstract: The title compound, C27H17F7S2, a new unsymmetrical photochromic dithienylethene with an ortho‐fluoro­phenyl substituent, is one of the most promising candidates for photoelectronic applications, such as optical storage, photoswitches and waveguides. There are two mol­ecules in the asymmetric unit. Both adopt a photoactive anti‐parallel conformation. For one mol­ecule, the distance between the two reactive C atoms is 3.572 (6) Å; the dihedral angles between the central cyclo­pentene ring and the thio­phene rin… Show more

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Cited by 6 publications
(5 citation statements)
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“…Of all the photochromic compounds, diarylethenes are the most promising candidates because of their good thermal stability, high sensitivity, fast response and high fatigue resistance (Irie, 2000;Tian & Yang, 2004). A large numbers of diarylethene crystal structures and their properties have already been reported (Matsuda & Irie, 2004;Morimoto et al, 2004;Morimoto & Irie, 2005;, including some structures we have determined (Pu et al, 2003(Pu et al, , 2004Pu, Fan et al, 2005;Pu, Li et al, 2005;Pu, Yang, Wang et al, 2005;Pu, Yang, Yan et al, 2005). For further background information see .…”
Section: Data Collectionmentioning
confidence: 89%
“…Of all the photochromic compounds, diarylethenes are the most promising candidates because of their good thermal stability, high sensitivity, fast response and high fatigue resistance (Irie, 2000;Tian & Yang, 2004). A large numbers of diarylethene crystal structures and their properties have already been reported (Matsuda & Irie, 2004;Morimoto et al, 2004;Morimoto & Irie, 2005;, including some structures we have determined (Pu et al, 2003(Pu et al, , 2004Pu, Fan et al, 2005;Pu, Li et al, 2005;Pu, Yang, Wang et al, 2005;Pu, Yang, Yan et al, 2005). For further background information see .…”
Section: Data Collectionmentioning
confidence: 89%
“…(3) (5.8 g, 20.3 mmol), was prepared in 89.7% yield by reacting 3-bromo-2methyl-5-thienylboronic acid, (2) (Pu, Li et al, 2005) (5.0 g, 22.6 mmol) with 4-bromo-1-chlorobenzene (4.3 g, 22.6 mmol) in the presence of Pd(PPh 3 ) 4 (0.8 g) and Na 2 CO 3 (2 mol l À1 , 84.8 mmol) in THF (100 ml) for 12 h at 343 K. To a stirred THF solution (80 ml) of compound (3) (5.8 g, 20.3 mmol), an n-BuLi/hexane solution (8.1 ml, 2.5 mol l À1 , 20.3 mmol) was added at 195 K under a nitrogen atmosphere. 30 min later, (2,5-dimethyl-3-thienyl)perfluorocyclo-pent-1-ene, (4) (Sun et al, 2003) (6.2 g, 20.3 mmol), was added and the mixture was stirred for 2 h at this temperature.…”
Section: Methodsmentioning
confidence: 99%
“…Compound (I) was prepared as outlined in the second scheme. 3-Bromo-2-methyl-5-(3-cyanophenyl)thiophene, (3) (5.5 g, 19.8 mmol), was prepared in 65% yield by reacting 3-bromo-2-methyl-5-thienylboronic acid, (2) (Pu, Li et al, 2005;2006) (6.8 g, 30.6 mmol), with 3bromo-1-cyanobenzene (5.6 g, 30.6 mmol) in the presence of Pd(PPh 3 ) 4 (0.9 g) and aqueous Na 2 CO 3 (2 M, 100.0 mmol) in tetrahydrofuran (THF; 90 ml) for 12 h at 343 K. To a stirred THF solution (50 ml) of compound (3) (1.5 g, 5.4 mmol), an n-BuLi-hexane solu-tion (3.4 ml, 1.6 M, 5.4 mmol) was added at 195 K under a nitrogen atmosphere. After 30 min (2,5-dimethyl-3-thienyl)perfluorocyclopent-1-ene, (4) (Sun et al, 2003) (1.7 g, 5.4 mmol), was added and the mixture was stirred for 2 h at this temperature.…”
Section: Methodsmentioning
confidence: 99%