2005
DOI: 10.1107/s1600536805036512
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1,2-Bis[5-(2,2-dicyanovinyl)-2-ethyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, a new photochromic diarylethene compound

Abstract: The title compound, C25H14N4F6S2, is a new symmetric photo­chromic diaryl­ethene which can potentially be applied in optoelectronic devices, such as optical memories, photo switches, and color displays. In the crystalline phase, this mol­ecule, which has crystallographic twofold rotation symmetry, adopts an anti­parallel conformation that can undergo effective photocyclization reactions by a conrotatory mechanism. The distance between the two reactive C atoms is 3.642 (7) Å. The dihedral angle between the cent… Show more

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Cited by 4 publications
(3 citation statements)
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“…From the viewpoint of applications to optical memory media and full color diaplays, it is desired to develop photochromic compounds that have sensitivity in the wavelength region of 650-830 nm (Irie, 2000;Gilat et al, 1993Gilat et al, , 1995. We have previously reported three dithienylethenes with dicyano subsitituent: 1,2-bis[2-methyl-5-(2,2′-dicyanovinyl)-3thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, 2-ethyl analog and 2-butyl analog (Pu et al, 2003(Pu et al, , 2005Zheng et al, 2007), which have relatively long wavelength absorption spectrum (> 700 nm). In order to investigate systematically the substituent effect at the 2-position of the thiophene rings of diarylethenes on their photochemical properties, we have now synthesized the title photochromic diarylethene, (Ia) (Scheme 1), and its structure is presented here.…”
Section: Supporting Informationmentioning
confidence: 99%
“…From the viewpoint of applications to optical memory media and full color diaplays, it is desired to develop photochromic compounds that have sensitivity in the wavelength region of 650-830 nm (Irie, 2000;Gilat et al, 1993Gilat et al, , 1995. We have previously reported three dithienylethenes with dicyano subsitituent: 1,2-bis[2-methyl-5-(2,2′-dicyanovinyl)-3thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, 2-ethyl analog and 2-butyl analog (Pu et al, 2003(Pu et al, , 2005Zheng et al, 2007), which have relatively long wavelength absorption spectrum (> 700 nm). In order to investigate systematically the substituent effect at the 2-position of the thiophene rings of diarylethenes on their photochemical properties, we have now synthesized the title photochromic diarylethene, (Ia) (Scheme 1), and its structure is presented here.…”
Section: Supporting Informationmentioning
confidence: 99%
“…The title compound, (Ia), was synthesized in 29% total yield by the literature method (Pu, Yang et al, 2005) using 5-nbutyl-thiophene-2-carbaldehyde as the start material. Crystal suitable for X-ray analysis were grown from a solution (diethyl ether/hexane 1/3) by slow evaporation at room temperature (m.p.…”
Section: S2 Experimentalmentioning
confidence: 99%
“…In the present work, the title photochromic diarylethene, (Ia), was synthesized, and its structure is presented here. Previously, we have reported the structure of the 2-methyl, (II), and 2-ethyl analog, (III), of this compound (Pu et al, 2003;Pu, Yang et al, 2005). In order to investigate the substituent effect at the 2-position of the thiophene on the photochemical properties, we have now determined the structure of (Ia).…”
mentioning
confidence: 99%