蒽醌醚及重氮衍生物的合成、表征及电致变色应用研究
|
摘要
电致变色是指材料在电场作用下,颜色会随着其氧化态和还原态的相互转化而发生可逆改变的一种现象。电致变色材料是一种会改变人们生活方式和人们对能源的利用方式的新型功能材料。电致变色材料在大型显示器、灵巧窗及电子纸等方面都有广泛的应用前景。有机电致变色材料因其色彩丰富、光学性能较好、颜色转换快、成本低廉、循环可逆性好、易进行分子设计优化性能,而受到青睐,是近年来电致变色研究的主要方向。
本文以1-氯蒽醌、2-氯蒽醌、2-氨基蒽醌为起始物,分别与苯酚、邻甲氧基苯酚、对硝基苯酚、双酚A、硝基苯胺、氨基苯甲酸、氨基苯磺酸反应,合成了苯氧基取代蒽醌、二蒽醌取代双酚A、2-蒽醌重氮氨基苯等14个目标化合物。~1H NMR和FT-IR表征结果表明,合成的化合物与设计结构一致。运用紫外可见光光度法和循环伏安法,对所制备的蒽醌化合物的光、电化学性质进行了测试。紫外可见光吸收光谱表明:不同类型的取代基对蒽醌化合物的光化学特征具有较大的影响。循环伏安测试(CV)结果表明,这些化合物都有两对明显的可逆的氧化还原峰。位于-0.80V左右的还原峰是由化合物的R与R~-之间的相互转化引起的;而位于-1.05V左右的还原峰则是由R~-与R~(2-)之间的相互转化引起的,这些物质具有良好的氧化还原性能。以这些蒽醌衍生物为电致变色材料、以高分子电解质为导电层组装了全固态型电致变色简易器件及纸载的固态型简易电致变色器件。性能测试实验表明:这些蒽醌类化合物具有比较好的电致变色性能,适合做电致变色材料。在外加电势的作用下,1-位取代苯氧基蒽醌由橙黄色转化为桔红色,2-位取代苯氧基蒽醌由黄色转化为红色,而2-蒽醌偶氮氨基苯系列化合物则由橙黄色转化为红色。全固态型器件及纸载器件各有其不同的优缺点,都需要进一步的优化和改进。蒽醌类物质原料易得、便宜,作为电致变色材料应该有很好的前景。
Electrochromism can be defined as the phenomenon of the electrochromic materials that undergo color reversible change upon oxidation or reduction,which is ensued from changing the potential applied charged..Electrochromic materials are a kind of newly-functional materials which can change people's life style and the way of utilizing energy sources.They can be widely applied to large-area display devices,smart windows and electronic papers.Owing to their plentiful colors,better optical performances,fast color change,low cost,good cycling reversibility,organic electrochromic materials have become a dominant direction in the electrochromic research in recent years.
In this paper,forteen target ahthraquinone derivatives,phenoxy substituted anthraquinones,O,O'-di(1/2-anthraquinonyl)bisphenol Aas,2-anthraquinonyldiazoamino-benzenes were synthesized starting from 1-chloroanthraquinone,2-chloroanthraquinone and 2-aminoanthraquinone.These compounds were characterized by 1~H NMR and FT-IR, and they were proved to be consistent with the designed structures.The spectro- and electrochemical properties of these compounds were determined by ultraviolet-visible spectrophotometry and cyclic voltammetry,respectively.The ultraviolet-visible absorption spectra suggest that substituted groups of different kinds can strongly influence the spectrochemical properties of anthraquinone derivatives.The cyclic voltammograms show that these compounds have two pairs of obvious redox peaks.The peak at about -0.80 V indicates the reduction potential for the transition from R to R~-,while that at about -1.05 V indicates the reduction potential for the transition from R~- to R~(2-).These compounds have favorable redox properties.With polyelectrolyte as ionic conduction layer,the simple solid EC devices and the liquid simple EC devices with paper as vector based on these compounds were assembled.Performance experimentals show these anthraquinone derivatives have efficient electrochromic behaviors and they are useful EC materials. When reduced,the device colors of 1-phenoxy substituted anthraquinones shift from saffron yellow to salmon pink,those of 2-phenoxy substituted anthraquinones change from yellow into red while those of 2-anthraquinonyldiazoaminoenzenes switch from orange to claret.Both the simple solid EC devices and the simple liquid EC devices with paper as vector have respective advantages and shortcomings respectively,and they both need further optimization and improvement.Anthraquinone derivatives will be good prospects as electrochromic materials as a result of their advantages in getting raw materials easily and low price.
本文以1-氯蒽醌、2-氯蒽醌、2-氨基蒽醌为起始物,分别与苯酚、邻甲氧基苯酚、对硝基苯酚、双酚A、硝基苯胺、氨基苯甲酸、氨基苯磺酸反应,合成了苯氧基取代蒽醌、二蒽醌取代双酚A、2-蒽醌重氮氨基苯等14个目标化合物。~1H NMR和FT-IR表征结果表明,合成的化合物与设计结构一致。运用紫外可见光光度法和循环伏安法,对所制备的蒽醌化合物的光、电化学性质进行了测试。紫外可见光吸收光谱表明:不同类型的取代基对蒽醌化合物的光化学特征具有较大的影响。循环伏安测试(CV)结果表明,这些化合物都有两对明显的可逆的氧化还原峰。位于-0.80V左右的还原峰是由化合物的R与R~-之间的相互转化引起的;而位于-1.05V左右的还原峰则是由R~-与R~(2-)之间的相互转化引起的,这些物质具有良好的氧化还原性能。以这些蒽醌衍生物为电致变色材料、以高分子电解质为导电层组装了全固态型电致变色简易器件及纸载的固态型简易电致变色器件。性能测试实验表明:这些蒽醌类化合物具有比较好的电致变色性能,适合做电致变色材料。在外加电势的作用下,1-位取代苯氧基蒽醌由橙黄色转化为桔红色,2-位取代苯氧基蒽醌由黄色转化为红色,而2-蒽醌偶氮氨基苯系列化合物则由橙黄色转化为红色。全固态型器件及纸载器件各有其不同的优缺点,都需要进一步的优化和改进。蒽醌类物质原料易得、便宜,作为电致变色材料应该有很好的前景。
Electrochromism can be defined as the phenomenon of the electrochromic materials that undergo color reversible change upon oxidation or reduction,which is ensued from changing the potential applied charged..Electrochromic materials are a kind of newly-functional materials which can change people's life style and the way of utilizing energy sources.They can be widely applied to large-area display devices,smart windows and electronic papers.Owing to their plentiful colors,better optical performances,fast color change,low cost,good cycling reversibility,organic electrochromic materials have become a dominant direction in the electrochromic research in recent years.
In this paper,forteen target ahthraquinone derivatives,phenoxy substituted anthraquinones,O,O'-di(1/2-anthraquinonyl)bisphenol Aas,2-anthraquinonyldiazoamino-benzenes were synthesized starting from 1-chloroanthraquinone,2-chloroanthraquinone and 2-aminoanthraquinone.These compounds were characterized by 1~H NMR and FT-IR, and they were proved to be consistent with the designed structures.The spectro- and electrochemical properties of these compounds were determined by ultraviolet-visible spectrophotometry and cyclic voltammetry,respectively.The ultraviolet-visible absorption spectra suggest that substituted groups of different kinds can strongly influence the spectrochemical properties of anthraquinone derivatives.The cyclic voltammograms show that these compounds have two pairs of obvious redox peaks.The peak at about -0.80 V indicates the reduction potential for the transition from R to R~-,while that at about -1.05 V indicates the reduction potential for the transition from R~- to R~(2-).These compounds have favorable redox properties.With polyelectrolyte as ionic conduction layer,the simple solid EC devices and the liquid simple EC devices with paper as vector based on these compounds were assembled.Performance experimentals show these anthraquinone derivatives have efficient electrochromic behaviors and they are useful EC materials. When reduced,the device colors of 1-phenoxy substituted anthraquinones shift from saffron yellow to salmon pink,those of 2-phenoxy substituted anthraquinones change from yellow into red while those of 2-anthraquinonyldiazoaminoenzenes switch from orange to claret.Both the simple solid EC devices and the simple liquid EC devices with paper as vector have respective advantages and shortcomings respectively,and they both need further optimization and improvement.Anthraquinone derivatives will be good prospects as electrochromic materials as a result of their advantages in getting raw materials easily and low price.
引文
[1]D R.Rosseinsky,R J.Mortimer.Electrochromic systems and the prospects for devices.[J].Adv.Mater.2001.13:783-793
[2]代富平.全固态电致变色器件(WO_3/SPE/NiO_x)的制备与研究.硕士学位论文.兰州:兰州大学,2002
[3]C.Xiong,A.E.Aliev,B.Gnade,K.J.Balkus,Jr..Fabrication of Silver Vanadium Oxide and V_2O_5 Nanowires for Electrochromics.[J].ACS Nano.2008.2(2):293-301
[4]B.Gorodetsky,N.R.Bidirectional Ring-Opening and Ring-Closing of Cationic 1,2-Dithienylcyclopentene Molecular Switches Triggered with Light or Electricity,[J].Adv.Funct.Mater.2007.17(5):786-796
[5]Elba G.-N.,L.Mugica,Jose V.-G.,J.Casado,J.T.L.Navarrete,J.Vecinan,C.Rovira,D.B.Amabilino.Synthesis and Doping of a Multifuctional Tetrathiafulvalene-Substitited Poly(isocyanide).[J].Macromolecules,2007.40(21):7521-7531
[6]D.W.Steuerman,H.-R.Tseng,A.J.Peters,A.H.Flood,J.O.Jeppesen,K.A.Nielsen,J.F.Stoddart,J.R.Heath.Molecular-Mechanical Switch-Based Solid-State Electrochromic Devices.[J].Angew.Chem.Int.Ed.2004.43:6486-6491
[7]F.PNicoletta,G.Chidichimo,D.Cupelli,G.De Filpo,M.De Benedittis,B.Gabriele,G.Salerno,A.Fazio.Electrochromic Polymer-Dispersed Liquid-Crystal Film:A New Bifunctional Device.[J].Adv.Funct.Mater.2005.15(6):995-999
[8]S.-H.Hsiao,G.-S.Lioy,Y.-C.Kung,H.-J.Yen.High Contrast Ratio and Rapid Switching Electrochromic Polymeric Films Based on 4-(Dimethylamino) triphenylamine-Functionalized Aromatic Polyamides.[J].Macromolecules,2008.41(8):2800-2808
[9]J.Gao,D.-G.Liu,J.-M.Sansinena,H.-L.Wang.Synthesis and Characterization of Electrochromic Polyamides with Well-Defined Molecular Structures and Redox Properties.[J].Adv.Funct.Mater.2004.14(6):537-543
[10]I.F.Perepichka,D.F.Perepichka,H.Meng,F.Wudl.Light-Emitting Polythiophenes.[J].Adv.Mater.2005.17:2281-2305
[11]R.M.Walczak,J.R.Reynolds.Poly(3,4-alkylenedioxypyrroles):The PXDOPs as Versatile Yet Underutilized Electroactive and Conducting Polymers.[J].Adv.Mater.2006.18:1121-1131
[12]C.W.Kim,S.W.Oh,Y.H.Kim,H.G.Cha,Y.S.Kang.Characterization of the Spironaphthooxazine Doped Photochromic Glass:The Effect of Matrix Polarity and Pore Size.[J].Phys.Chem.C,2008.112(4):1140-1145
[13]V.FTraven,A.Y.Bochkov,M.M.Krayushkin,V.N.Yarovenko,B.V.Nabatov,S.M.Dolotov,V.A.Barachevsky,I.P.Beletskaya.Coumarinyl(thienyl)thiazoles:Novel Photochromes with Modulated Fluorescence.[J].Org.Lett.2008.10(6):1319-1322
[14]D.Pijper,M.G..M.Jongejan,A.Meetsma,B.L.Feringa.Light-Controlled Supramolecular Helicity of a Liquid Crystalline Phase Using a Helical Polymer Functionalized with a Single Chiroptical Molecular Switch.[J].Am.Chem.Soc.2008.130(13):4541-4552
[15]T.T.To,C.B.Duke,C.S.Junker,C.M.O'Brien,C.R.Ross,C.E.Barnes,C.E.Webster,T.J.Burkey.Linkage Isomerization as a Mechanism for Photochromic Materials:Cyclopentadienylmanganese Tricarbonyl Derivatives with Chelatable Functional Groups.[J].Organometallics,2008.27(2):289-296
[16]G.G.Gao,L.Xu,X-S.Qu,H.Liu,Y-Y.Yang.New Approach to the Synthesis of an Organopolymolybdate Polymer in Aqueous Media by Linkage of Multicarboxylic Ligands.[J].Inorg.Chem.2008.47(8):3402-3407
[17]N.Malic,J.A.Campbell,R.A.Evans.Superior Photochromic Performance of Naphthopyrans in a Rigid Host Matrix Using Polymer Conjugation:Fast,Dark,and Tunable.[J].Macromolecules,2008.41(4):1206-1214
[18]H.J.Kim,J.H.Jang,H.Choi,T.Lee,J.Ko,M.Yoon,H-J.Kim.Photoregulated Fluorescene.Switching in Axially Coordinated Tin (Ⅳ)Porphyrinc Dithienylethene.[J].Inorg.Chem.2008.47(7):2411-2415
[19]K.Ueno,K.Matsubara,M.Watanabe,Y.Takeoka.An Electro-and Themochromic Hydrogel as a Full-Color Indicator.[J].Adv.Mater.2007.19:2807-2812
[20]J.Harada,T.Fujiwara,K.Ogawan.Crucial Role of Fluorescence in the Solid-State Thermochromism of Salicylideneanilines.[J].J.Am.Chem.Soc.2007.129(51):16216-16221
[21]N.Baho,D.Zargarian.Diphenyl(dipyrazolyl)methane Complexes of Ni:Synthesis,Structural Characterization,and Chromotropism of NiBr_2 Derivatives.[J].Inorg.Chem.2007.46(18):7621-7632
[22]A.Potisatityuenyong,R.Rojanathanes,G.Tumcharern,M.Sukwattanasinitt.Electronic Absorption Spectroscopy Probed Side-Chain Movement in Chromic Transitions of Polydiacetylene Vesicles.[J].Langmuir,2008.ASAP Article
[23]Rodolfo C.-S.,Layza Arizmendi,Mayela D.-A.,Jorge R.-G..PH-and Thermosensitive Polyaniline Colloidal Particles Prepared by Enzymatic Polymerizationg.[J].Langmuir,2007.23(1):8-12
[24]S.Dei,A.Matsumoto,A.Matsumoto.Thermochromism of Polydiacetylenes in the Solid State and in Solution by the Self-Organization of Polymer Chains Containing No Polar Group.[J].Macromolecules,2008.41(7):2467-2473
[25]M.Gaudon,A.E.Thiry,A.Largeteau,P.Deniard,S.Jobic,J.Majimel,A.Demourgues. Characterizaton of the Piezochromic Behavior of Some Members of the CuMo_(1-x)W_xO_4Series.[j].Inorg.Chem.2008.47(7):2404-2410
[26]J.Mizuguchi,N.Tanifuji,K.Kobayashi.Electronic and Structural Characterizationg of a Piezochromic Indigoid:11-(3'-Oxodihydrobenzothiophen-2'-ylidence) cyclopenta [1,2-b:4,3-b']dibenzothiophene.[J].Phys.Chem.B,2003.107(46):12635-12638
[27]Y.Sagara,T.Mutai,I.Yoshikawa,K.Araki.Material Design for Piezochromic Luminescence:Hydrogen-Bond-Directed Assemblices of a Pyrene Derivative.[J].J.Am.Chem.Soc,2007.129(6):1520-1521
[28]J.Engelking,D.Ulbrich,H.Menzel.Piezochromic Effect and Orientational Order in Monolayers,and LB Multilayers of Poly(p-phenylenesulfonate)- Dioctadecyl - dimethylammonium Bromide Complexes.[J].Macromolrcules,2000.33(24):9026-9033
[29]A.Qin,J.W.Y.Lam,H.Dong,W.Lu,C.K.W.Jim,Y.Dong,M.Hussler,H.H.Y.Sung,I.D.Williams,G.K.L.Wong,B.Z.Tang.Metal-Free,Regioselective Diyne Polycyclotrimerization Synthesis,Photoluminescence,Solvatochromism,and Two-Photon Absorption of a Triphenylamine-Containing Hyperbranched Poly(aroylarylene).[J].Macromolecules,2007.40(14):4879-4886
[30]A.J.Boydston,P.D.Vu,O.L.Dykhno,V.Chang,A.R.Wyatt,A.S.Stockettt,E.T.Ritschdoff,J.B.Shear,C.W.Bielawski.Modular Fluorescent Benzobis(imidazolium) Salts:Syntheses,Photophysical Analyses,and Applications.[J].Am.Chem.Soc,2008.130(10):3143-3156
[31]A.A.Ishchenko,A.V.Kulinich,S.L.Bondarev,V.N.Knyukshto.Photodynamics of Polyene-Polymethine Transformations and Spectral Fluorescent Properties of Merocyanine Dyes.[J].J.Phys.Chem.A,2007.111(51):13629-13637
[32]E.L.Spitler,J.M.Monson,M.M.Haley.Structure-Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl) benzenes and Bis(dehydrobenzoannuleno)benzenes.[J].Org.Chem,2008.73(6):2211-2223
[33]F.Terenziani,C.Sissa,A.Painelli.Symmetry Breaking in Octupolar Chromophores:Solvatochromism and Electroabsorption.[J].J.Phys.Chem.B,2008.ASAP Article
[34]李天文,刘鸿生.变色材料的研究与应用.现代化工.2004.24(2):62
[35]王旭东,徐伟箭.可逆热致变色材料的应用新进展.2000.3:42-45
[36]沈庆月,陆春华,许仲梓.光致变色材料的研究与应用.2005.19(10):31-35
[37]Bessiere A.,Duhamel C.,Badot J.C.Study and Optimization of a flexible electrochromic device based on polyanilin.Electrochimica Acta.2004.49:2051-2055
[38]P M S.Monk,R J.Mortimer,D R.Rosseinsky.Electrochromism:Fundamentals and Applicationa.[M].VCH,Weinheim 1995
[39]Bonhote P.,Gogniat E.,Campus F.Nanocrystalline electrochromic displays.Displays.1999.20:137-144.
[40]Rosseinsky D.R.,Mortimer R.J.Electrochromic Systems and the Prospects for Devices.Advanced Materials.2001.13(11):783-793
[41]傅相锴,罗伟.电子墨水显示技术的研究进展.2005.36(10):1477-1481
[42]F.Wohlex,[J].Pogg.Ann,1924.2:350
[43]O.Glemser,H.Snner.[J].Z Anorg Allg Chem.1943.252:144
[44]J.R.Platt.[J].J.Chem.Phys.1961.34(3):862
[45]Wohlex F.[J].Pogg Ann.1924.2:350
[46]Glemser O,Snner H.[J].Z Anorg Allg Chem.1943.252:144
[47]Glenser O,Naumann C.[J].Z Anorg Allg Chem,1951.265:288
[48]S.K.Deb.The reversible colouration-bleaching process in tungsten trioxide under the action of an applied electric field.[J].Appl.Opt.Suppl.1969.3:193
[49]S.K.Deb.Optial and Photoelectric Properties and Colour Cencres in Thin Films of Tungsten Oxides.[J].Philos.Mag.1973.27:801-822
[50]丘思畴等.直流溅射法制备电致变色NiOx膜.科学通报.1994.39(10):896-898
[51]Schoot C J,Ponjee J J,et al.[J].Appl Phys Lett.1973.23(2):64
[52]Lampert C M.[J].Solar Energy Mater.1984.11:1
[53]Lampert C M.[J].Optical Engineering.1984,23(1):92
[54]Lampert C M.[J].Solar Energy Mater.1982.11(4):162
[55]Svensson J S E M,Grangvist C G.[J].Proc SPIE.1984.30:502
[56]Shoot C J,Projee J J.New electrochromic memory display.Appl.Phys.Lett.1973.23(2):64-65
[57]Dan Wood.[J].Advanced display.2002.4:23
[58]篠崎研二等.日本索尼公司.[P].中国专利,2001,申请号:01808702.7
[59]饶凯.全固态电致变色器件的研究.[硕士学位论文].重庆:西南师范大学,2004
[60]周杰,傅相锴,孙美丹等.PEO掺杂氧化镍薄膜的溶胶-凝胶法制备及电致变色性能研究.化学学报.2006.64(10):1004-1010
[61]周杰,傅相锴,饶凯.四元掺杂电致变色薄膜材料的制备及其性能的研究.功能材料.2005.36(3):419-424
[62]蒋庆龙,傅相锴,陈祝君.烯烃取代的紫罗精合成及全固态电致变色器件[J].应用化学,2007,24(9):1032-1035.
[63]孙炎,傅相锴,陈祝君,等.非对称紫精化合物的合成表征及电致变色性能[J].精细化工,2008,25(5):438-441.
[64]马丽华,傅相锴,罗伟,等.水溶性导电聚苯胺-磺化聚(苯乙烯-丙烯酸)复合物的制 备和表征[J].材料导报,2006:4-40.
[65]陈蔚,傅相锴,马丽华.聚苯胺/聚苯乙烯磺酸-聚乙烯醇电致变色膜及制备方法.[J].功能材料,2008,39(1):60-63.
[66]Jiang Q L,Fu X K,Chen Z J.The synthesis of polymerisable viologens and their electrochromic property on ITO glass.[J].Chinese Chemical Letters,2006.17(11):1447-1450.
[67]冯博学,陈冲,何毓阳,伞海生等.电致变色材料及器件的研究进展.功能材料.2004.2(35):145-149
[68]K H.C.,Yom J.,Moon B.,Lee H.S.Electrochimica Acta.2003.48:4127
[69]Kim H.,Pyo M.Journal of Applied Electrochemistry.2000.30:49
[70]Byker H.J.Electrochimica Acta.2001,46(13),2015
[71]Mortimer R.J.Electrochim.Acta.1999.44:2971
[72]Dalton E.F.,Murray R.W.J.Phys.Chem.1991.95:6383
[73]Amabilino D.B.,Stoddart J.F.Chem.Rev.1995.95:2725
[74]Monk Paul M.S.,Roger J.Mortimer,David R.Rosseinsky.Electrochromism:fundamentals and applications.Weinheim:VCH.1995.Ch.2.
[75]Bird C.L.,Kuhn A.T.Chem.Soc.Rev.1981.10:49
[76]Kawaguchi Y,Harada A,Org.Lett.2002.2:1353
[77]Murakami H,Kawabuchi,Kotoo K,et al.J.Am.Chem.Soc.1997.119:7605
[78]Satoshi Hashimoto,Hideki Matsuoka.J.Appl.Phys.1991.69(2):15
[79]Kuo chuan Ho,David E Singleton,Charles B Greenberg.J.Electrochem.Soc.1990.127(12):3858-3864
[80]D.L.White,G..N.Taylor,J.Appl.Phys.1974.45:4718
[81]Scrosati B.Applications of Electroactive Polymers[M].London:Chapman& Halls,1998
[82]Trombach N,Hild O,Schlettwein.[J].Mater.Chem.2002.12(4):879
[83]Mercier V M M.van der Sluis P.[J].Solid State Ionics.2001.145(124):17
[84]Notten P H L.[J].Solid State Mater Sci.1999.4(1):5
[85]游效曾.分子材料-光电功能化合物.上海:上海科学技术出版社,2001,268
[86]C M Elliott,S J Schmittle,J G Redepenning,E M Balk.J.Macromol Sci-Chem 1988.A25:1215
[87]A.Bolognesi,M.Catellani,S.Destri,et al.J.Chem.Soc.Chem.Commun.1988.246
[88]Rauh R D.Electrochimic Acta.1999.44:3165-3176
[89]Kitani A.,et al.J.Electro.Chem.1986.209:227
[90]Thakoor S.,et aI.J.Appl.Phys.1990.67:3132
[91]Wenqiang Qiao,Jia Zheng,Yufeng Wang,Yijun Zheng,(?) Naiheng Song,Xinhua Wan,and Zhi Yuan Wang,Efficient Synthesis and Properties of Novel Near-Infrared Electrochromic Anthraquinone Imides.[J].Organic Letters.2008.10(4):641-644
[92]林里,杨建洲,徐亮,染料中间体2-甲基蒽醌的合成工艺探讨,[J].染料与染色,2004.41(5):289-290
[93]张玉红,赵华绒,俞庆森,含蒽醌基单偶氮染料光电导性质构效研究,[J].化学学报,2002.60(8):1513-1516
[94]吴赛苏,蒽醌型离子染料的合成及应用,[J].化学工程师,2001.84(3)
[95]张玉红,赵华绒,含蒽酯基单偶氮染料光电导性质构效研究,[J].化学学报,2002.60(8):
[96]陈琼华,戴汉松,苏学良.中药大黄的综合研究.ⅩⅩⅪ.大黄蒽醌衍生物系统分离的改进方法[J].天然产物研究与开发.,2002,13(3):58-60.
[97]袁倚盛,赵飞浪,谭力.大黄游历蒽醌的制备与纯化[J].中草药,2000,31(7):508-509.
[98]吕泰省,易杨华,毛士龙,等.铁刀木的葸醌类成分[J].药学学报,2001,36(7):547-548.
[99]张国庆,陈万生,纪松岗.高效毛细管电泳法分离模拟混合的何首乌中7种蒽醌类成分的研究[J].药学实践杂志,1999,17(6):352-354
[100]于超,兰红梅,王宇.HPLC法测定不同产地决明子中五种蒽醌类化合物[J].基层中药杂志,2002,16(2):8-10
[101]罗文毓,江萍.大黄中5种蒽醌衍生物HPLC测定[J].药物分析杂志,1989,9(5):259-262
[102]胡世荣,何亚三,蒽醌衍生物的合成与光谱特性,[J].合成化学.2006.14(2):154-156
[103]胡世荣,刘颖,金正哲,3-甲基-1-苯氧基-9,10-蒽醌及其衍生物的合成和光致变色性,[J].延边大学学报.2004.30(4):267-269
[104]H J Byker(Gentex Corp.).US Patent 5751467,1998
[105]D.V.Varaprasad,I.A.McCabe,H.Habibi,N.R.Lynam,et al.US Patent 5724187.1998
[106]詹姆斯·H·沙克尔特三世,菲利普·M·享利,理查德·斯奈德等.中国专利CN1515949,申请号:02155783.7,1997
[107]L·瓦尔德,M·莫勒.用于高分辨率图像的显示器及其生产方法.中国专利CN1571939,申请号02812977.6,2002.
[108]M·T·约翰逊,N·D·杨.具有用于调节串扰的电极的电致变色显示板.中国专利CN1662847,申请号:03814676.2,2003
[109]M·T·约翰逊,L·J·M·施兰根,H·J·B·贾格特.具有不同电致变色材料的电致变色彩色显示器.中国专利CN1672189,申请:03817852.4,2003
[110]J·R·雷诺兹,K·宗,I·施温德曼等.电致变色聚合物和聚合物电致变色装置.中国专利CN1615352,申请号:02827322.2,2002
[2]代富平.全固态电致变色器件(WO_3/SPE/NiO_x)的制备与研究.硕士学位论文.兰州:兰州大学,2002
[3]C.Xiong,A.E.Aliev,B.Gnade,K.J.Balkus,Jr..Fabrication of Silver Vanadium Oxide and V_2O_5 Nanowires for Electrochromics.[J].ACS Nano.2008.2(2):293-301
[4]B.Gorodetsky,N.R.Bidirectional Ring-Opening and Ring-Closing of Cationic 1,2-Dithienylcyclopentene Molecular Switches Triggered with Light or Electricity,[J].Adv.Funct.Mater.2007.17(5):786-796
[5]Elba G.-N.,L.Mugica,Jose V.-G.,J.Casado,J.T.L.Navarrete,J.Vecinan,C.Rovira,D.B.Amabilino.Synthesis and Doping of a Multifuctional Tetrathiafulvalene-Substitited Poly(isocyanide).[J].Macromolecules,2007.40(21):7521-7531
[6]D.W.Steuerman,H.-R.Tseng,A.J.Peters,A.H.Flood,J.O.Jeppesen,K.A.Nielsen,J.F.Stoddart,J.R.Heath.Molecular-Mechanical Switch-Based Solid-State Electrochromic Devices.[J].Angew.Chem.Int.Ed.2004.43:6486-6491
[7]F.PNicoletta,G.Chidichimo,D.Cupelli,G.De Filpo,M.De Benedittis,B.Gabriele,G.Salerno,A.Fazio.Electrochromic Polymer-Dispersed Liquid-Crystal Film:A New Bifunctional Device.[J].Adv.Funct.Mater.2005.15(6):995-999
[8]S.-H.Hsiao,G.-S.Lioy,Y.-C.Kung,H.-J.Yen.High Contrast Ratio and Rapid Switching Electrochromic Polymeric Films Based on 4-(Dimethylamino) triphenylamine-Functionalized Aromatic Polyamides.[J].Macromolecules,2008.41(8):2800-2808
[9]J.Gao,D.-G.Liu,J.-M.Sansinena,H.-L.Wang.Synthesis and Characterization of Electrochromic Polyamides with Well-Defined Molecular Structures and Redox Properties.[J].Adv.Funct.Mater.2004.14(6):537-543
[10]I.F.Perepichka,D.F.Perepichka,H.Meng,F.Wudl.Light-Emitting Polythiophenes.[J].Adv.Mater.2005.17:2281-2305
[11]R.M.Walczak,J.R.Reynolds.Poly(3,4-alkylenedioxypyrroles):The PXDOPs as Versatile Yet Underutilized Electroactive and Conducting Polymers.[J].Adv.Mater.2006.18:1121-1131
[12]C.W.Kim,S.W.Oh,Y.H.Kim,H.G.Cha,Y.S.Kang.Characterization of the Spironaphthooxazine Doped Photochromic Glass:The Effect of Matrix Polarity and Pore Size.[J].Phys.Chem.C,2008.112(4):1140-1145
[13]V.FTraven,A.Y.Bochkov,M.M.Krayushkin,V.N.Yarovenko,B.V.Nabatov,S.M.Dolotov,V.A.Barachevsky,I.P.Beletskaya.Coumarinyl(thienyl)thiazoles:Novel Photochromes with Modulated Fluorescence.[J].Org.Lett.2008.10(6):1319-1322
[14]D.Pijper,M.G..M.Jongejan,A.Meetsma,B.L.Feringa.Light-Controlled Supramolecular Helicity of a Liquid Crystalline Phase Using a Helical Polymer Functionalized with a Single Chiroptical Molecular Switch.[J].Am.Chem.Soc.2008.130(13):4541-4552
[15]T.T.To,C.B.Duke,C.S.Junker,C.M.O'Brien,C.R.Ross,C.E.Barnes,C.E.Webster,T.J.Burkey.Linkage Isomerization as a Mechanism for Photochromic Materials:Cyclopentadienylmanganese Tricarbonyl Derivatives with Chelatable Functional Groups.[J].Organometallics,2008.27(2):289-296
[16]G.G.Gao,L.Xu,X-S.Qu,H.Liu,Y-Y.Yang.New Approach to the Synthesis of an Organopolymolybdate Polymer in Aqueous Media by Linkage of Multicarboxylic Ligands.[J].Inorg.Chem.2008.47(8):3402-3407
[17]N.Malic,J.A.Campbell,R.A.Evans.Superior Photochromic Performance of Naphthopyrans in a Rigid Host Matrix Using Polymer Conjugation:Fast,Dark,and Tunable.[J].Macromolecules,2008.41(4):1206-1214
[18]H.J.Kim,J.H.Jang,H.Choi,T.Lee,J.Ko,M.Yoon,H-J.Kim.Photoregulated Fluorescene.Switching in Axially Coordinated Tin (Ⅳ)Porphyrinc Dithienylethene.[J].Inorg.Chem.2008.47(7):2411-2415
[19]K.Ueno,K.Matsubara,M.Watanabe,Y.Takeoka.An Electro-and Themochromic Hydrogel as a Full-Color Indicator.[J].Adv.Mater.2007.19:2807-2812
[20]J.Harada,T.Fujiwara,K.Ogawan.Crucial Role of Fluorescence in the Solid-State Thermochromism of Salicylideneanilines.[J].J.Am.Chem.Soc.2007.129(51):16216-16221
[21]N.Baho,D.Zargarian.Diphenyl(dipyrazolyl)methane Complexes of Ni:Synthesis,Structural Characterization,and Chromotropism of NiBr_2 Derivatives.[J].Inorg.Chem.2007.46(18):7621-7632
[22]A.Potisatityuenyong,R.Rojanathanes,G.Tumcharern,M.Sukwattanasinitt.Electronic Absorption Spectroscopy Probed Side-Chain Movement in Chromic Transitions of Polydiacetylene Vesicles.[J].Langmuir,2008.ASAP Article
[23]Rodolfo C.-S.,Layza Arizmendi,Mayela D.-A.,Jorge R.-G..PH-and Thermosensitive Polyaniline Colloidal Particles Prepared by Enzymatic Polymerizationg.[J].Langmuir,2007.23(1):8-12
[24]S.Dei,A.Matsumoto,A.Matsumoto.Thermochromism of Polydiacetylenes in the Solid State and in Solution by the Self-Organization of Polymer Chains Containing No Polar Group.[J].Macromolecules,2008.41(7):2467-2473
[25]M.Gaudon,A.E.Thiry,A.Largeteau,P.Deniard,S.Jobic,J.Majimel,A.Demourgues. Characterizaton of the Piezochromic Behavior of Some Members of the CuMo_(1-x)W_xO_4Series.[j].Inorg.Chem.2008.47(7):2404-2410
[26]J.Mizuguchi,N.Tanifuji,K.Kobayashi.Electronic and Structural Characterizationg of a Piezochromic Indigoid:11-(3'-Oxodihydrobenzothiophen-2'-ylidence) cyclopenta [1,2-b:4,3-b']dibenzothiophene.[J].Phys.Chem.B,2003.107(46):12635-12638
[27]Y.Sagara,T.Mutai,I.Yoshikawa,K.Araki.Material Design for Piezochromic Luminescence:Hydrogen-Bond-Directed Assemblices of a Pyrene Derivative.[J].J.Am.Chem.Soc,2007.129(6):1520-1521
[28]J.Engelking,D.Ulbrich,H.Menzel.Piezochromic Effect and Orientational Order in Monolayers,and LB Multilayers of Poly(p-phenylenesulfonate)- Dioctadecyl - dimethylammonium Bromide Complexes.[J].Macromolrcules,2000.33(24):9026-9033
[29]A.Qin,J.W.Y.Lam,H.Dong,W.Lu,C.K.W.Jim,Y.Dong,M.Hussler,H.H.Y.Sung,I.D.Williams,G.K.L.Wong,B.Z.Tang.Metal-Free,Regioselective Diyne Polycyclotrimerization Synthesis,Photoluminescence,Solvatochromism,and Two-Photon Absorption of a Triphenylamine-Containing Hyperbranched Poly(aroylarylene).[J].Macromolecules,2007.40(14):4879-4886
[30]A.J.Boydston,P.D.Vu,O.L.Dykhno,V.Chang,A.R.Wyatt,A.S.Stockettt,E.T.Ritschdoff,J.B.Shear,C.W.Bielawski.Modular Fluorescent Benzobis(imidazolium) Salts:Syntheses,Photophysical Analyses,and Applications.[J].Am.Chem.Soc,2008.130(10):3143-3156
[31]A.A.Ishchenko,A.V.Kulinich,S.L.Bondarev,V.N.Knyukshto.Photodynamics of Polyene-Polymethine Transformations and Spectral Fluorescent Properties of Merocyanine Dyes.[J].J.Phys.Chem.A,2007.111(51):13629-13637
[32]E.L.Spitler,J.M.Monson,M.M.Haley.Structure-Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl) benzenes and Bis(dehydrobenzoannuleno)benzenes.[J].Org.Chem,2008.73(6):2211-2223
[33]F.Terenziani,C.Sissa,A.Painelli.Symmetry Breaking in Octupolar Chromophores:Solvatochromism and Electroabsorption.[J].J.Phys.Chem.B,2008.ASAP Article
[34]李天文,刘鸿生.变色材料的研究与应用.现代化工.2004.24(2):62
[35]王旭东,徐伟箭.可逆热致变色材料的应用新进展.2000.3:42-45
[36]沈庆月,陆春华,许仲梓.光致变色材料的研究与应用.2005.19(10):31-35
[37]Bessiere A.,Duhamel C.,Badot J.C.Study and Optimization of a flexible electrochromic device based on polyanilin.Electrochimica Acta.2004.49:2051-2055
[38]P M S.Monk,R J.Mortimer,D R.Rosseinsky.Electrochromism:Fundamentals and Applicationa.[M].VCH,Weinheim 1995
[39]Bonhote P.,Gogniat E.,Campus F.Nanocrystalline electrochromic displays.Displays.1999.20:137-144.
[40]Rosseinsky D.R.,Mortimer R.J.Electrochromic Systems and the Prospects for Devices.Advanced Materials.2001.13(11):783-793
[41]傅相锴,罗伟.电子墨水显示技术的研究进展.2005.36(10):1477-1481
[42]F.Wohlex,[J].Pogg.Ann,1924.2:350
[43]O.Glemser,H.Snner.[J].Z Anorg Allg Chem.1943.252:144
[44]J.R.Platt.[J].J.Chem.Phys.1961.34(3):862
[45]Wohlex F.[J].Pogg Ann.1924.2:350
[46]Glemser O,Snner H.[J].Z Anorg Allg Chem.1943.252:144
[47]Glenser O,Naumann C.[J].Z Anorg Allg Chem,1951.265:288
[48]S.K.Deb.The reversible colouration-bleaching process in tungsten trioxide under the action of an applied electric field.[J].Appl.Opt.Suppl.1969.3:193
[49]S.K.Deb.Optial and Photoelectric Properties and Colour Cencres in Thin Films of Tungsten Oxides.[J].Philos.Mag.1973.27:801-822
[50]丘思畴等.直流溅射法制备电致变色NiOx膜.科学通报.1994.39(10):896-898
[51]Schoot C J,Ponjee J J,et al.[J].Appl Phys Lett.1973.23(2):64
[52]Lampert C M.[J].Solar Energy Mater.1984.11:1
[53]Lampert C M.[J].Optical Engineering.1984,23(1):92
[54]Lampert C M.[J].Solar Energy Mater.1982.11(4):162
[55]Svensson J S E M,Grangvist C G.[J].Proc SPIE.1984.30:502
[56]Shoot C J,Projee J J.New electrochromic memory display.Appl.Phys.Lett.1973.23(2):64-65
[57]Dan Wood.[J].Advanced display.2002.4:23
[58]篠崎研二等.日本索尼公司.[P].中国专利,2001,申请号:01808702.7
[59]饶凯.全固态电致变色器件的研究.[硕士学位论文].重庆:西南师范大学,2004
[60]周杰,傅相锴,孙美丹等.PEO掺杂氧化镍薄膜的溶胶-凝胶法制备及电致变色性能研究.化学学报.2006.64(10):1004-1010
[61]周杰,傅相锴,饶凯.四元掺杂电致变色薄膜材料的制备及其性能的研究.功能材料.2005.36(3):419-424
[62]蒋庆龙,傅相锴,陈祝君.烯烃取代的紫罗精合成及全固态电致变色器件[J].应用化学,2007,24(9):1032-1035.
[63]孙炎,傅相锴,陈祝君,等.非对称紫精化合物的合成表征及电致变色性能[J].精细化工,2008,25(5):438-441.
[64]马丽华,傅相锴,罗伟,等.水溶性导电聚苯胺-磺化聚(苯乙烯-丙烯酸)复合物的制 备和表征[J].材料导报,2006:4-40.
[65]陈蔚,傅相锴,马丽华.聚苯胺/聚苯乙烯磺酸-聚乙烯醇电致变色膜及制备方法.[J].功能材料,2008,39(1):60-63.
[66]Jiang Q L,Fu X K,Chen Z J.The synthesis of polymerisable viologens and their electrochromic property on ITO glass.[J].Chinese Chemical Letters,2006.17(11):1447-1450.
[67]冯博学,陈冲,何毓阳,伞海生等.电致变色材料及器件的研究进展.功能材料.2004.2(35):145-149
[68]K H.C.,Yom J.,Moon B.,Lee H.S.Electrochimica Acta.2003.48:4127
[69]Kim H.,Pyo M.Journal of Applied Electrochemistry.2000.30:49
[70]Byker H.J.Electrochimica Acta.2001,46(13),2015
[71]Mortimer R.J.Electrochim.Acta.1999.44:2971
[72]Dalton E.F.,Murray R.W.J.Phys.Chem.1991.95:6383
[73]Amabilino D.B.,Stoddart J.F.Chem.Rev.1995.95:2725
[74]Monk Paul M.S.,Roger J.Mortimer,David R.Rosseinsky.Electrochromism:fundamentals and applications.Weinheim:VCH.1995.Ch.2.
[75]Bird C.L.,Kuhn A.T.Chem.Soc.Rev.1981.10:49
[76]Kawaguchi Y,Harada A,Org.Lett.2002.2:1353
[77]Murakami H,Kawabuchi,Kotoo K,et al.J.Am.Chem.Soc.1997.119:7605
[78]Satoshi Hashimoto,Hideki Matsuoka.J.Appl.Phys.1991.69(2):15
[79]Kuo chuan Ho,David E Singleton,Charles B Greenberg.J.Electrochem.Soc.1990.127(12):3858-3864
[80]D.L.White,G..N.Taylor,J.Appl.Phys.1974.45:4718
[81]Scrosati B.Applications of Electroactive Polymers[M].London:Chapman& Halls,1998
[82]Trombach N,Hild O,Schlettwein.[J].Mater.Chem.2002.12(4):879
[83]Mercier V M M.van der Sluis P.[J].Solid State Ionics.2001.145(124):17
[84]Notten P H L.[J].Solid State Mater Sci.1999.4(1):5
[85]游效曾.分子材料-光电功能化合物.上海:上海科学技术出版社,2001,268
[86]C M Elliott,S J Schmittle,J G Redepenning,E M Balk.J.Macromol Sci-Chem 1988.A25:1215
[87]A.Bolognesi,M.Catellani,S.Destri,et al.J.Chem.Soc.Chem.Commun.1988.246
[88]Rauh R D.Electrochimic Acta.1999.44:3165-3176
[89]Kitani A.,et al.J.Electro.Chem.1986.209:227
[90]Thakoor S.,et aI.J.Appl.Phys.1990.67:3132
[91]Wenqiang Qiao,Jia Zheng,Yufeng Wang,Yijun Zheng,(?) Naiheng Song,Xinhua Wan,and Zhi Yuan Wang,Efficient Synthesis and Properties of Novel Near-Infrared Electrochromic Anthraquinone Imides.[J].Organic Letters.2008.10(4):641-644
[92]林里,杨建洲,徐亮,染料中间体2-甲基蒽醌的合成工艺探讨,[J].染料与染色,2004.41(5):289-290
[93]张玉红,赵华绒,俞庆森,含蒽醌基单偶氮染料光电导性质构效研究,[J].化学学报,2002.60(8):1513-1516
[94]吴赛苏,蒽醌型离子染料的合成及应用,[J].化学工程师,2001.84(3)
[95]张玉红,赵华绒,含蒽酯基单偶氮染料光电导性质构效研究,[J].化学学报,2002.60(8):
[96]陈琼华,戴汉松,苏学良.中药大黄的综合研究.ⅩⅩⅪ.大黄蒽醌衍生物系统分离的改进方法[J].天然产物研究与开发.,2002,13(3):58-60.
[97]袁倚盛,赵飞浪,谭力.大黄游历蒽醌的制备与纯化[J].中草药,2000,31(7):508-509.
[98]吕泰省,易杨华,毛士龙,等.铁刀木的葸醌类成分[J].药学学报,2001,36(7):547-548.
[99]张国庆,陈万生,纪松岗.高效毛细管电泳法分离模拟混合的何首乌中7种蒽醌类成分的研究[J].药学实践杂志,1999,17(6):352-354
[100]于超,兰红梅,王宇.HPLC法测定不同产地决明子中五种蒽醌类化合物[J].基层中药杂志,2002,16(2):8-10
[101]罗文毓,江萍.大黄中5种蒽醌衍生物HPLC测定[J].药物分析杂志,1989,9(5):259-262
[102]胡世荣,何亚三,蒽醌衍生物的合成与光谱特性,[J].合成化学.2006.14(2):154-156
[103]胡世荣,刘颖,金正哲,3-甲基-1-苯氧基-9,10-蒽醌及其衍生物的合成和光致变色性,[J].延边大学学报.2004.30(4):267-269
[104]H J Byker(Gentex Corp.).US Patent 5751467,1998
[105]D.V.Varaprasad,I.A.McCabe,H.Habibi,N.R.Lynam,et al.US Patent 5724187.1998
[106]詹姆斯·H·沙克尔特三世,菲利普·M·享利,理查德·斯奈德等.中国专利CN1515949,申请号:02155783.7,1997
[107]L·瓦尔德,M·莫勒.用于高分辨率图像的显示器及其生产方法.中国专利CN1571939,申请号02812977.6,2002.
[108]M·T·约翰逊,N·D·杨.具有用于调节串扰的电极的电致变色显示板.中国专利CN1662847,申请号:03814676.2,2003
[109]M·T·约翰逊,L·J·M·施兰根,H·J·B·贾格特.具有不同电致变色材料的电致变色彩色显示器.中国专利CN1672189,申请:03817852.4,2003
[110]J·R·雷诺兹,K·宗,I·施温德曼等.电致变色聚合物和聚合物电致变色装置.中国专利CN1615352,申请号:02827322.2,2002