Crystal Structure and Crystalline State Multiphotochromism Properties of a Fused Diarylethene Dimer
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摘要
The crystal structure of fused photochromic diarylethene dimer, 1,4-bis-[4-(4-{2-(5-phenyl)-2-methyl-thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-enyl}-5-methyl-thiophen-2-yl) buta-1,3-diyne(1 oo, C46 H23 F12 S4) was determined by single-crystal X-ray diffraction analysis. This crystal belongs to the triclinic system, space group P1 with a = 7.546(3), b = 8.869(3), c = 16.196(5), α = 98.000(4)°, β = 100.803(4)°, γ = 98.449(4)°, Z = 2, V = 1037.6(6) ?~3, Dc = 1.496 mg/m~3, μ = 0.317, F(000) = 474, the final R = 0.0428 and wR = 0.1199 for 4115 observed reflections(I > 2σ(I)). Further study demonstrated this compound underwent reversible photochromism with color-switching between colorlessness and green in crystalline state. Upon 365 nm irradiation, the diarylethene shows one step photochromism to form isomer 1 oc. When irradiated with 312 nm, the stepwise photocyclization reactions occurred in diarylethene dimer through the line of 1 oo to 1 oc to 1 cc.
The crystal structure of fused photochromic diarylethene dimer, 1,4-bis-[4-(4-{2-(5-phenyl)-2-methyl-thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-enyl}-5-methyl-thiophen-2-yl) buta-1,3-diyne(1 oo, C46 H23 F12 S4) was determined by single-crystal X-ray diffraction analysis. This crystal belongs to the triclinic system, space group P1 with a = 7.546(3), b = 8.869(3), c = 16.196(5), α = 98.000(4)°, β = 100.803(4)°, γ = 98.449(4)°, Z = 2, V = 1037.6(6) ?~3, Dc = 1.496 mg/m~3, μ = 0.317, F(000) = 474, the final R = 0.0428 and wR = 0.1199 for 4115 observed reflections(I > 2σ(I)). Further study demonstrated this compound underwent reversible photochromism with color-switching between colorlessness and green in crystalline state. Upon 365 nm irradiation, the diarylethene shows one step photochromism to form isomer 1 oc. When irradiated with 312 nm, the stepwise photocyclization reactions occurred in diarylethene dimer through the line of 1 oo to 1 oc to 1 cc.
The crystal structure of fused photochromic diarylethene dimer, 1,4-bis-[4-(4-{2-(5-phenyl)-2-methyl-thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-enyl}-5-methyl-thiophen-2-yl) buta-1,3-diyne(1 oo, C46 H23 F12 S4) was determined by single-crystal X-ray diffraction analysis. This crystal belongs to the triclinic system, space group P1 with a = 7.546(3), b = 8.869(3), c = 16.196(5), α = 98.000(4)°, β = 100.803(4)°, γ = 98.449(4)°, Z = 2, V = 1037.6(6) ?~3, Dc = 1.496 mg/m~3, μ = 0.317, F(000) = 474, the final R = 0.0428 and wR = 0.1199 for 4115 observed reflections(I > 2σ(I)). Further study demonstrated this compound underwent reversible photochromism with color-switching between colorlessness and green in crystalline state. Upon 365 nm irradiation, the diarylethene shows one step photochromism to form isomer 1 oc. When irradiated with 312 nm, the stepwise photocyclization reactions occurred in diarylethene dimer through the line of 1 oo to 1 oc to 1 cc.
引文
(1)Irie, M.; Fukaminato, T.; Matsuda, K.; Kobatake, S. Photochromism of diarylethene molecules and crystals:memories, switches, and actuators.Chem. Rev. 2014, 114, 12174–12277.
(2)Zhang, J. J.; Tian, H. The endeavor of diarylethenes:new structures, high performance, and bright future. Adv. Opt. Mater. 2018, 6, 1701278.
(3)Fan, C. B.; Pu, S. Z.; Liu, G. Effects of solvents on the growth of an asymmetrical photochromic diarylethene crystal. Dyes Pigments 2015, 113,61–69.
(4)Zhang,C.C.;Zhu,L.;Fan,C.B.;Pu,S.Z.Crystalstructureandphotoreactivepropertiesof1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(N-(quinolin-8-yl)-2-carboxamide)-3-thienyl)]perfluorocyclopentene. Chin.J. Struct. Chem. 2016, 35, 413–420.
(5)Higashiguchi, K.; Matsuda, K.; Tanifuji, N.; Irie, M. Full-color photochromism of a fused dithienylethene trimer. J. Am. Chem. Soc. 2005, 127,8922–8923.
(6)Chen,J.X.;Wang,J.Y.;Zhang,Q.C.;Chen,Z.N.MulitphotochromisminanasymmetricRutheniumcomplexwithtwodifferent dithienylethenes. Inorg. Chem. 2017, 56, 13257–13266.
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(8)Li,B.;Wang,J.Y.;Wen,H.M.;Shi,L.X.;Chen,Z.N.Redox-modulatedstepwisephotochromisminarutheniumcomplexwithdual dithienylethene-acetylides. J. Am. Chem. Soc. 2012, 134, 16059–16067.
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(11)Arai, R.; Uemura, S.; Irie, M.; Matsuda, K. Reversible photoinduced change in molecular ordering of diarylethene derivatives at a solution-HOPG interface. J. Am. Chem. Soc. 2008, 130, 9371–9379.
(12)Wong,H.L.;Tao,C.H.;Zhu,N.Y.;Yam,V.W.W.Photochromicalkynesasversatilebuildingblocksformetalalkynylsystems:design,synthesis, and photochromic studies of diarylethene-containing platinum(II)phosphine alkynyl complexes. Inorg. Chem. 2011, 50, 471–481.
(13)Higashiguchi, K.; Matsuda, K.; Irie, M. Photochromic reaction of a fused dithienylethene:multicolor photochromism. Angew. Chem. Int. Ed. 2003,42, 3537–3540.
(14)Delbaere, S.; Vermeersch, G.; Frigoli, M.; Mehl, G. H. Bridging the visible:the modulation of the absorption by more than 450 nm. Org. Lett.,2010, 12, 4090–4093.
(15)Li,B.;Wen,H.M.;Wang,J.Y.;Shi,L.X.;Chen,Z.N.Modulatingstepwisephotochromisminplatinum(II)complexeswithdual dithienylethene-acetylides by a progressive red shift of ring-closure absorption. Inorg. Chem. 2013, 52, 12511–12520.
(16)Li, B.; Wen, H. M.; Wang, J. Y.; Shi, L. X.; Chen, Z. N. Multistate and multicolor photochromism through selective cycloreversion in asymmetric platinum(II)comlexes with two different dithienylethene-acetylides. Inorg. Chem. 2015, 54, 11511–11519.
(17)Zhang, D. B.; Wang, J. Y.; Jacquemin, D.; Chen, Z. N. Spectroscopic and electrochemical properties of ruthenium complexes with photochromic triarylamine-dithienylethene-acetylide ligands. Inorg. Chem. Front. 2016, 3, 1432–1443.
(18)Li,B.;Wu,Y.H.;Wen,H.M.;Shi,L.X.;Chen,Z.N.Gold(I)-coordinationtriggeredmultistepandmultiplephotochromicreactionsin multi-dithienylethene(DTE)systems. Inorg. Chem. 2012, 51, 1933–1942.
(19)Zhang,D.B.;Fan,C.B.;Zheng,C.H.;Pu,S.Z.Anewdithienylethenedimerwithterminaltertiaryamineredoxcenters:electrochemical,UV-vis-NIR spectral and electronic transfer charges induced by a stepwise photochromic process. Dyes Pigments 2017, 136, 669–677.
(20)Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. C 2015, 71, 3–8.
(21)Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry. Verlag Chemie GmbH, Weinheim 1969, 781–932.
(22)Ramamurthy, V.; Venkatesan, K. Photochemical reactions of organic crystals. Chem. Rev. 1987, 87, 433–481.
(23)Jia,H.J.;Fan,C.B.;Pu,S.Z.Crystalstructureandphotochromicpropertiesof[1-(2-methyl-5-(4-cyanophenyl)-3-thienyl)]-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene. Chin. J. Struct. Chem. 2015, 34, 208–214.
(2)Zhang, J. J.; Tian, H. The endeavor of diarylethenes:new structures, high performance, and bright future. Adv. Opt. Mater. 2018, 6, 1701278.
(3)Fan, C. B.; Pu, S. Z.; Liu, G. Effects of solvents on the growth of an asymmetrical photochromic diarylethene crystal. Dyes Pigments 2015, 113,61–69.
(4)Zhang,C.C.;Zhu,L.;Fan,C.B.;Pu,S.Z.Crystalstructureandphotoreactivepropertiesof1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(N-(quinolin-8-yl)-2-carboxamide)-3-thienyl)]perfluorocyclopentene. Chin.J. Struct. Chem. 2016, 35, 413–420.
(5)Higashiguchi, K.; Matsuda, K.; Tanifuji, N.; Irie, M. Full-color photochromism of a fused dithienylethene trimer. J. Am. Chem. Soc. 2005, 127,8922–8923.
(6)Chen,J.X.;Wang,J.Y.;Zhang,Q.C.;Chen,Z.N.MulitphotochromisminanasymmetricRutheniumcomplexwithtwodifferent dithienylethenes. Inorg. Chem. 2017, 56, 13257–13266.
(7)Fihey, A.; Perrier, A.; Browne, W. R.; Jacquemin, D. Multiphotochromic molecular systems. Chem. Soc. Rev. 2015, 44, 3719–3759.
(8)Li,B.;Wang,J.Y.;Wen,H.M.;Shi,L.X.;Chen,Z.N.Redox-modulatedstepwisephotochromisminarutheniumcomplexwithdual dithienylethene-acetylides. J. Am. Chem. Soc. 2012, 134, 16059–16067.
(9)Guerchais, V.; Ordronneau, L.; Bozec, H. L. Recent developments in the field of metal complexes containing photochromic ligands:modulation of linear and nonlinear optical properties. Coord. Chem. Rev. 2010, 254, 2533–2545.
(10)Morimoto, M.; Kobatake, S.; Irie, M. Multicolor photochromism of two-and three-component diarylethene crystals. J. Am. Chem. Soc. 2003, 125,11080–11087.
(11)Arai, R.; Uemura, S.; Irie, M.; Matsuda, K. Reversible photoinduced change in molecular ordering of diarylethene derivatives at a solution-HOPG interface. J. Am. Chem. Soc. 2008, 130, 9371–9379.
(12)Wong,H.L.;Tao,C.H.;Zhu,N.Y.;Yam,V.W.W.Photochromicalkynesasversatilebuildingblocksformetalalkynylsystems:design,synthesis, and photochromic studies of diarylethene-containing platinum(II)phosphine alkynyl complexes. Inorg. Chem. 2011, 50, 471–481.
(13)Higashiguchi, K.; Matsuda, K.; Irie, M. Photochromic reaction of a fused dithienylethene:multicolor photochromism. Angew. Chem. Int. Ed. 2003,42, 3537–3540.
(14)Delbaere, S.; Vermeersch, G.; Frigoli, M.; Mehl, G. H. Bridging the visible:the modulation of the absorption by more than 450 nm. Org. Lett.,2010, 12, 4090–4093.
(15)Li,B.;Wen,H.M.;Wang,J.Y.;Shi,L.X.;Chen,Z.N.Modulatingstepwisephotochromisminplatinum(II)complexeswithdual dithienylethene-acetylides by a progressive red shift of ring-closure absorption. Inorg. Chem. 2013, 52, 12511–12520.
(16)Li, B.; Wen, H. M.; Wang, J. Y.; Shi, L. X.; Chen, Z. N. Multistate and multicolor photochromism through selective cycloreversion in asymmetric platinum(II)comlexes with two different dithienylethene-acetylides. Inorg. Chem. 2015, 54, 11511–11519.
(17)Zhang, D. B.; Wang, J. Y.; Jacquemin, D.; Chen, Z. N. Spectroscopic and electrochemical properties of ruthenium complexes with photochromic triarylamine-dithienylethene-acetylide ligands. Inorg. Chem. Front. 2016, 3, 1432–1443.
(18)Li,B.;Wu,Y.H.;Wen,H.M.;Shi,L.X.;Chen,Z.N.Gold(I)-coordinationtriggeredmultistepandmultiplephotochromicreactionsin multi-dithienylethene(DTE)systems. Inorg. Chem. 2012, 51, 1933–1942.
(19)Zhang,D.B.;Fan,C.B.;Zheng,C.H.;Pu,S.Z.Anewdithienylethenedimerwithterminaltertiaryamineredoxcenters:electrochemical,UV-vis-NIR spectral and electronic transfer charges induced by a stepwise photochromic process. Dyes Pigments 2017, 136, 669–677.
(20)Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. C 2015, 71, 3–8.
(21)Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry. Verlag Chemie GmbH, Weinheim 1969, 781–932.
(22)Ramamurthy, V.; Venkatesan, K. Photochemical reactions of organic crystals. Chem. Rev. 1987, 87, 433–481.
(23)Jia,H.J.;Fan,C.B.;Pu,S.Z.Crystalstructureandphotochromicpropertiesof[1-(2-methyl-5-(4-cyanophenyl)-3-thienyl)]-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene. Chin. J. Struct. Chem. 2015, 34, 208–214.