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两亲性二茂铁衍生物的合成及其性质表征
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摘要
二茂铁(ferrocene)衍生物具有独特的结构和光电性质,在电化学、材料科学、分子器件、催化、生物医学等方面有广泛的应用。本论文合成了系列两亲性的二茂铁基衍生物并研究了电化学性质及成膜性能,研究内容如下:
     1、设计并合成了系列新型两亲性分子N-长链烷基二茂铁基甲胺,碘化N,N-二甲基长链烷基二茂铁基甲铵盐,1,1'-N,N-长链烷基二茂铁基甲胺,1,1'-碘化N,N-二甲基长链烷基二茂铁基甲铵盐。
     2、利用循环伏安法(CV)、常规脉冲法(NPV)、计时电流法(CA)、计时电量法(CC)等多种电化学技术研究了两亲性二茂铁衍生物的电化学性质。研究结果表明:二茂铁基甲铵盐中的二茂铁基的矢量电位显著变化,并且茂环上H原子取代情况对矢量电位影响较大,但是N原子上连结的烷基链的长短对矢量电位影响较小,此外,讨论了不同取代基对化合物的电极过程动力学参数的影响。
     3、制备了两种两亲性二茂铁基甲铵盐化合物2b、4b注膜修饰电极。运用循环伏安、差示脉冲等电化学方法研究了修饰电极的电化学性质,得到了修饰电极的动力学参数,为其在电化学传感器方面的应用提供依据。
     4、研究了二茂铁衍生物的气液界面行为,发现它们能够形成稳定的Langmuir膜。利用紫外-可见吸收光谱研究了化合物Langmuir-Blodgett(LB)膜的转移情况,利用原子力显微镜观察了单层LB膜的表面形貌,用光学测厚仪测得了单层膜的厚度并推测了化合物在基板上的空间取向及聚集状态。利用化合物3c LB膜修饰电极,考察了LB膜电极与DNA之间的相互作用,为其在生物医药和电化学传感器方面的应用提供理论依据。
Ferrocenyl derivatives are used widely in electrochemistry,material science, molecular device,biomedicine,and catalysis due to the sandwich structures and the photoelectricity character of ferrocene.In this paper,ferrocenyl derivatives were synthesized and their electrochemistry and their Langmuir-Blodgett(LB) films characterization were investigated.
     1.Series of new amphiphilic Fc moiety derivatives have been synthesized,such as N-ferrocenylmethylalkylamine,N,N-dimethyl-ferrocenylalkylammonium iodide, 1,1'-N,N-ferroeenylmethylalkylamine,1,1'-N,N-dimethyl-ferrocenylalkyl-ammonium iodide.
     2.The electrochemical properties of these compounds were investigated by electrochemical methods such as cyclic voltammetry,normal pulse voltammetry, chronoamperometry and chronocoulometry.Results showed that the redox character affected by the substituent on the H atom in Fc and the half-wave potential E~0 was not almost affected by the substituent on the N atom.The dynamical parameters of electrode process affected by the substituent were also investigated.
     3.Electrode modified with two new amphiphilic ferrocenyl derivatives 2b and 4b casted film were made.The electrochemical properties and dynamical parameters of modified electrode were investigated with electrochemical methods such as cyclic voltammetry,differential pulse voltammetry.The results provided some useful information for voltammetric sensors designed appliation.
     4.The Langmuir monolayer film and Langmuir-Blodgett(LB) films of these new amphiphilic ferrocenyl derivatives were fabricated.The gas/liquid interface behavior of these compounds was investigated.The results showed that ferrocenyl derivatives could form stable monolayer film at the air/water interface.The multilayer behavior of the ferrocenyl derivatives was examined by UV spectra,the morphology of monolayer was observed by AFM,the thickness of one-layer LB film was measured and the mode in the films was presumed.Electrode modified with 3c LB films was fabricated and the interaction of 3c LB films modified electrode and DNA was researched,which provided some information for biomedicine and sensors.
引文
[1]Y.J.Kealy,EL.Panson.A new type of organ-iron compound.[J].Nature,1951,168:1039-1040.
    [2]G.Wilkinson,M.Rosenblum,M.C.Whiting,R.B.Woodward.The structure of iron biscyclopentadienyl.J.Am.Chem.Soc.,1952,74:2125-2126.
    [3]S.Carter,J.N.Murrell.The barrier to internal rotation in metallocenes.Journal of Organometallic Chemistry,1980,192(3):399-408.
    [4]王世华,无机化学教程.北京:科学出版社,2000,197.
    [5]钱延龙,陈新滋.金属有机化学与催化.北京:化学工业出版社,1997,45.
    [6]Toyne,J.Kenneth,Thompson,N.James.Ferrocene compounds for liquid crystals.Brit.Uk Pat.,Appl 1994,24.
    [7]T.N.Ghosh.Extension of Michael's reaction.J.Indian Chem.Soc.,1935,12:692-698.
    [8]C.Lmpard,J.A.Muphy,N.Lewis.On the mechanism of homolytic acylation of ferrocenes.Tetrahedron Lett.,1991,37(32):4993-4994.
    [9]J.K.Lindsay,C.R.Hauser.Aminomethylation of ferrocene to form N,N-dimethylamino methylferrocene and its conversion to the corresponding alcohol and aldehyde.Journal of Organic Chemistry,1957,22:355-358.
    [10]U.T.Muelle-wreserhtoff,G.Ingrain.A simple synthesis of metallocene aldehydes from lithiometallocenes and N,N-dimethylformamide:Ferrocene and ruthenocene aldehydes and 1,1'-dialdehydes.J.Organomet.Chem.,1993,463(1-2):163-167.
    [11]王鹏,景晓燕,梅K松.两种ω-二茂铁羧酸的改进合成及其电化学行为,化学试剂,2000,22(4),196-197.
    [12]蒲陆梅,莫尊理,杨武.含二茂铁单元的分子树络合物的电化学性质,化学试剂,2001,23(1):21-23.
    [13]郭栋,莫宏,屠晓燕.一个新的二茂铁-钴四核双螺旋配合物的合成,结构和电化学性质研究,无机化学学报,2003,19(1):54-58.
    [14]钱鹰,孙岳明,刘举正.具有电子给-受体结构的二茂铁衍生物的分子二阶非线性极化率,功能材料,1998,56(4):340-346.
    [15]B.Bildstein,M.Malaun,H.Kopacka.Heterocyclic carbenes with N-ferrocenyl-N-methylsubstitution:synthesis,reactivity,structure and electrochemistry.J.Org.Chem.,1999,572(2):177-187.
    [16]M.Sato,K.Fukui,M.Sakamoto.Charge transfer between two ferrocene groups linked by oligothiophene.Thin Solid Films,2001,393(1):210-216.
    [17]A.Rosenfeld,J.Blum,D.Gibson,A.Ramu.Preparation,characterization and antileukemic properties of diaminemalonatoplatinum(Ⅱ) complexes tethered to ferrocene.Inorganica Chimica Acta,1992,201(2):219-221.
    [18]杨庆华,叶宪曾,陶家洵.二茂铁单羧基衍生物/Nation修饰电极对多巴胺的电化学催化研究.北京大学学报(自然科学版),1999,35(6):38-44.
    [19]M.Okochi,N.Nakamura,T.Matsuaga,Oceamographic Literature Review.1996,43:953-955.
    [20]C.D.Hall.Macrocycles and cryptands containing the ferrocene unit.Ferrocenes,1995,279-316.
    [21]P.D.Beer,Z.Chen,M.Drew,J.Kingston,M.Ogden,P.Spencer.New polyaza and polyamm-onium ferrocene macrocyclic ligands that complex and electrochemically recognize transition metal cations and phosphate anions in water.Journal of the Chemical Society,Chemical Communications,1993,(13):1046-1048.
    [22]Hu Ping,Zhao Ke-Qing,Zhang Liang-Fu.Synthesis of a new cholesteric liquid crystal and study on the effect of substitutional group on its mesomorphous behavior.Sichuan Shifan Daxue Xuebao,Ziran Kexueban,1997,20(6):107-110.
    [23]M.Sato,H.Kono,I.Motogmaa,K.Hata.Simple modification of Vilsmeier method for the preparation of formylferrocene.Chem.Soc.,Jpn,1968,41(1):252.
    [24]R.Myron,R.B.Woodward.The structure and chemistry of ferrocene.Ⅲ.Evidence pertaining to the ring rotational barrier.J.Am.Chem.Soc.,1958,80:5443-5449.
    [25]R.T.Bronson,T.S.Bradshaw,P.B.Svage,S.Fuangswasdi,S.C.Lee,K.E.Krakowika,R.M.lzatt.Bis-8-hydroxyquinoline-Armed Diazatrithia-15-crown-5 and Diazatrithia-16-crown-5 Ligands:Possible Fluorophoric Metal Ion Sensors.J.Org.Chem.,2001,66(14):4752-4758.
    [26]G.M.Sheldriek.Porgram for refining crystal structure refinement.Univesity of Gottingen,Germany,1997.
    [27]M.L.H.Green,R.S.Marder.Synthesis and Structure of(cis)-[1-ferrocenyl-2-(4-nitrop-henyl ethylene)],an Organotransition Metal Compoundwith a Large Second-order Optical Nonlinearity.[J]Nature,1987,330(6145):360-326.
    [28]Ferraris,John,Cowan.Electron transfer in a new highly conducting donor-acceptor complex.J.Am.Chem.Soc.,1973,95(3):948-949.
    [29]袁耀锋,含新型二茂铁配体的多核金属有机配合物的合成与性质研究,[D]大津:南开大学,93.
    [30]T.Izmui,S.Oohashi,Y.Tate.Synthesis and complexing properties of bis-crown ethers incorporating benzo-15-crown-5 and metallocene.J.HeteroCycl Chem,1993,30(4):967-975.
    [31]P.D.Beer,C.G.Grane,A.D.Keefe.Potassium selective metallocene cryptand molecules.J.Organomet Chem,1986,314,C9.
    [32]A.Rosenfeld,J.Blum.reparation characterization and antileukemic properties of diaminemalonatoplatinum(Ⅱ) complexes tethered to ferrocene.Imorg.Chem.Acta,1992,201,219.
    [33]A.Ratajczak,A.Czech.Recovery of inducing optically active 1-ferrocenylethyl-amine in the synthesis of alanine by asymmetric transamination.Bulletin de 1'Academie Polonaise des Sciences,Serie des Sciences Chimiques,1979,27(9):661-664.
    [34]B.Tomapatanaget,T.Tuntulani,O.Chailapakul.Calix[4]arenes Containing Ferrocene Amide as Carboxylate Anion Receptors and Sensors.Org.Lett.,2003,5(9):1539-42.
    [35]J.C.Moutet,S.A.Eric,M.Ungureanu.Electropolymerization of ferrocene bis-amide derivatives:a possible route to an electrochemical sensory device.Electroanal.Chem.,1996,410(1):79-85.
    [36]黄耀曾,钱延龙.金属有机化学进展.北京:化学工业出版社,1987,20.
    [37]L.X.Dai,T.Tu,S.L.You,W.P.Deng,X.L.Hou.Asymmetric Catalysis with Chiral Ferrocene Ligands.Accounts of Chemical Research,2003,36(9):659-667.
    [38](a) S.L.You,Y.G.Zhou,X.L.Hou,L.X.Dai.Enantioselective palladium catalyzed allylic substitution with chiral thioether derivatives of ferrocenyl-oxazoline and the role of planar chirality in this reaction.Chemical Communications(Cambridge),1998,(24):2765-2766.(b)S.L.You,X.L.Hou,L.X.Dai.Synthesis of planar chiral selenide derivatives of ferrocenyl-oxazoline and their application in enantioselective palladium catalyzed allylic substitution reaction.Tetrahedron:Asymmetry,2000,11(7):1495-1500.
    [39](a) W.P.Deng,X.L.Hou,L.X.Dai,X.W.Dong.Efficient planar chiral 2'-substituted 1,1' -P,N-ferrocene ligands for the asymmetric Heck reaction:control of enantioselectivity and configuration by planar chiral substituent.Chemical Communications(Cambridge),2000,(16):1483-1484.(b) W.P.Deng,X.L.Hou,L.X.Dai,Y.H.Yu,W.Xia.On the role of planar chirality:a tunable enantioselectivity in palladium-catalyzed allylic alkylation with planar chiral 1,1'-P,N-ferrocene ligands.Chemical Communications(Cambridge),2000,(4):285-286.
    [40]W.P.Deng,S.L.You,X.L.Hou,L.X.Dai,Y.H.Yu,W.Xia,J.Sun.Importance of Planar Chirality in Chiral Catalysts with Three Chiral Elements:The Role of Planar Chirality in 2'-Substituted 1,1'-P,N-Ferrocene Ligands on the Enantioselectivity in Pd-Catalyzed Allylic Substitution.Journal of the American Chemical Society,2001,123(27):6508-6519.
    [41]J.Kuehnert,M.Dusek,J.Demel,H.Lang,P.Stepnicka.Synthesis,coordination and catalytic use of 1-(diphenylphosphino)-1'-carbamoylferrocenes with pyridyl-containing N-substituents.Dalton Transactions,2007,(26):2802-2811.
    [42]支永刚,韩杰,董春娥.手性二茂铁膦配体在不对称催化反应中的应用.合成化学,2000,8(5):384-394.
    [43]R.A.Durst,A.J.Baumner,R.W.Murray,R.P.Buck,C.P.Andrieux.Chemically modified electrodes:recommended terminology and definitions.Pure and Applied Chemistry.,1997,69(6):1317-1323.
    [44]董绍俊,车广礼,谢远武.化学修饰电极.北京:科学出版社,2003,28.
    [45]F.Dias,L.Newton,D.Ribeiro do Carmo.Stripping voltammetry of mercury(Ⅱ) with a chemically modified carbon paste electrode containing silica gel functionalized with 2,5-dimercapto-1,3,4-thiadiazole.Electroanalysis,2005,17(17):1540-1546.
    [46]M.I.Prodromidis,P.G.Veltsistas,M.I.Karayannis.Electrochemical Study of Chemically Modified and Screen-Printed Graphite Electrodes with[SbVO(CHL)2]Hex.Application for the Selective Determination of Sulfide.Analytical Chemistry,2000,72(17):3995-4002.
    [47]H.Cai,X.Cao,Y.Jiang,P.He,Y.Fang.Carbon nanotube-enhanced electrochemical DNA biosensor for DNA hybridization detection.Analytical and Bioanalytical Chemistry,2003,375(2):287-293.
    [48]C.Fang,X.Zhou.The electrochemical characteristics of C60-glutathione modified Au electrode and the electrocatalytic oxidation of NADH.Electroanalysis,2001,13(11):949-954.
    [49]L.Zhang,X.Lin.Covalent modification of glassy carbon electrodes with glycine for voltammetric separation of dopamine and ascorbic acid.Fresenius' Journal of Analytical Chemistry,2001,370(7):956-962.
    [50]K.C.Honeychurch,J.P.Hart,D.C.Cowell,D.W.M.Arrigan.Voltammetric behavior and trace determination of cadmium at a calixarene modified screen-printed carbon electrode.Electroanalysis,2002,14(3):177-185.
    [51]E.Staes,L.J.Nagels.Determination of electroinactive organic acids with LC and amperometric detection,using a PPy coated electrode.Talanta,2000,52(2):277-284.
    [52]G.Favaro,M.Fiorani.Determination of pharmaceutical thiols by liquid chromatography with electrochemical detection:Use of an electrode with a conductive carbon cement matrix,chemically modified with cobalt phthalocyanine.Analytica Chimica Acta,1996,332(2-3):249-255.
    [53]G.Sittampalam,G.S.Wilson.Surface-modified electrochemical detector for liquid chromatography.Analytical Chemistry,1983,55(9):1608-1610.
    [54]M.N.Alcada,J.L.Lima,M.C.Montenegro.FIA titrations of ephedrine in pharmaceutical formulations with a PVC tetraphenylborate tubular electrode.Journal of pharmaceutical and biomedical analysis,1995,13(4-5):459-464.
    [55]N.A.El-Maali,J.Wang.Tris(2,2'-bipyridyl)dichloro-ruthenium(Ⅱ) modified carbon paste electrodes for electrocatalytic detection of DNA.Sensors and Actuators,B:Chemical,2001,B76(1-3):211-214.
    [56]李平,吴守国,张汉吕,马超雄.尿酸在普鲁士蓝修饰电极上的电化学行为及其分析应用.分析化学,2005,33(1):77-79.
    [57]K.V.Gobi,Y.Sato,F.Mizutani.Mediatorless superoxide dismutase sensors using cytochrolne c-modified electrodes:xanthine oxidase incorporated polyion complex membrane for enhanced activity and in vivo analysis.Electroanalysis,2001,13(5):397-403.
    [58]S.Takenaka,Yamashita,M.Takagi,Y.Uto,H.Kondo.DNA Sensing on a DNA Probe-Modified Electrode Using Ferrocenylnaphthalene Diimide as the Electrochemically Active Ligand.Analytical Chemistry,2000,72(6):1334-1341.
    [59]Q.Gao,W.Wang,Y.Ma,X.Yang.Electrooxidative polymerization of phenothiazine derivatives on screen-printed carbon electrode and its application to determine NADH in flow injection analysis system.Talanta,2004,62(3):477-482.
    [60]R.Blonder,I.Ben-Dov,A.Dagan,I.Willner,E.Zisman.Photochemically-activated electrodes:application in design of reversible immunosensors and antibody patterned interfaces.Biosensors & Bioelectronics,1997,12(7):627-644.
    [61]M.Liang,S.Liu,M.Wei,L.Guo.Photoelectrochemical Oxidation of DNA by Ruthenium Tris(bipyridine) on a Tin Oxide Nanoparticle Electrode.Analytical Chemistry,2006,78(2):621-623.
    [62]S.M.Marxer,M.H.Schoenfisch.Sol-Gel Derived Potentiometric pH Sensors.Analytical Chemistry 2005,77(3):848-853.
    [63]P.C.Pandey,S.Upadhyay,G.Singh,R.Prakash,R.C.Srivastava,P.K.Seth.A new solid-state pH sensor and its application in the construction of all solid-state urea biosensor.Electroanalysis,2000,12(7):517-521.
    [64]S.Wang,D.Du.Differential pulse voltammetry determination of ascorbic acid with ferrocene-L-cysteine self-assembled supramolecular film modified electrode.Sensors and Actuators,B:Chemical 2004,B97(2-3):373-378.
    [65]孙向英,刘斌,李佳,徐金瑞.聚吡咯固定L-氨基酸氧化酶手性电极的制作及其应用.分析化学,2000,28(6):741-744.
    [66]汪尔康.21世纪的分析化学[M].北京:科学出版社.1999,1.
    [67]A.E.Cass,G.Davis,G.D.Francis,H.A.Hill,W.J.Aston,I.J.Higgins,E.V.Plotkin,L.D.Scott,A.P.Turner.Ferrocene-mediated enzyme electrode for amperometric determination of glucose.Analytical chemistry,1984,56(4):667-671.
    [68]L.Gorton,H.I.Karan,P.D.Hale,T.Inagaki,Y.Okamoto,T.A.Skotheim.A glucose electrode based on carbon paste chemically modified with a ferrocene-containing siloxane polymer and glucose oxidase,coated with a poly(ester-sulfonic acid) cation-exchanger.Analytica Chimica Acta,1990,228(1):23-30.
    [69]G.Jonsson,L.Gorton,L.Pettersson.Mediated electron transfer from glucose oxidase at a ferrocene-modified graphite electrode.Electroanalysis,1989,1(1):49-55.
    [70]彭孝军,王积涛.含二茂铁电子传递体的葡萄糖氧化酶电极研究.南开大学学报(自然科学,1996,29(4):67-70.
    [71]程广军,于化忠,邵会波.二茂铁硫醇自组装膜的电化学行为及其离子对效应.高等学校化学学报,1997,18(7):1141-1146.
    [72]S.Therias,B.Lacroix,B.Schollhorn,C.Mousty,P.Palvadeau.Electrochemical study of ferrocene and nitroxide derivatives intercalated in Zn-Cr and Zn-Al layered double hydroxides.Journal of Electroanalytical Chemistry,1998,454(1-2):91-97.
    [73]J.Moutet,E.Saint-Aman,M.Ungureanu,T.Visan.Electropolymerization of ferrocene bis-amide derivatives:a possible route to an electrochemical sensory device.Journal of Electroanalytical Chemistry,1996,410(1):79-85.
    [74]董绍俊,刘柏峰,毕军.一种新型的化学修饰电极电位传感器.科学通报,1984,(6):30-33.
    [75]武雪梅,栾积毅,李敬芬.酞菁包埋二茂铁聚合膜修饰电极对抗坏血酸的电催化.黑龙江医药科学,2003,26(4):17-18.
    [76]李亚卓,张素霞,李晓芳.基丁溶胶-凝胶技术的聚烯丙胺基二茂铁化学修饰电极的组装及其抗坏血酸的电催化氧化.高等学校化学学报,2003,24(8):1373-1376.
    [77]A.W.亚当森[美国]著,顾惕人译,表面的物理化学[M].科学出版社.1984.
    [78]崔大付.LB膜的物理性能与应用[J].物理学报,1996,25(1):54-63.
    [79]H.Kuhn.Functionalized monolayer assembly manipulation.[J].Thin solid films,1983,99(1-3):1-16.
    [80]C.Bubeck.Preparation and characterization of mono-and multilayers.Polymer Journal (Tokyo,Japan),199t,23(5):603-611.
    [81]C.D.Gutsche,B.Dhawan,K.H.No,R.Muthukrishnan.Calixarenes.4.The synthesis,characterization,and properties of the calixarenes from p-tert-butylphenol.Journal of the American Chemical Society,1981,103(13):3782-3792.
    [82]T.Maruyama,G.Fuller,C.Frank,C.Robertson.Flow-induced molecular orientation of a Langmuir film.Science(Washington,D.C.),1996,274(5285):233-235.
    [83]C.J.L.Constantino,T.Lemma,P.A.Antunes,R.Aroca.Single-molecule detection using surface-enhanced resonance Raman scattering and Langmuir-Blodgett monolayers.Analytical Chemistry,2001,73(15):3674-3678.
    [84]Y.Du,H.Wei,J.Kang,J.Yah,X.Yin,X.Yang,E.Wang.Microchip Capillary Electrophoresis with Solid-State Electrochemiluminescence Detector.Analytical Chemistry,2005,77(24):7993-7997.
    [85]江龙,以分子器件为背景的仿生膜.化学进展,1994,6(3):195-208.
    [86]J.A.Zasadzinski,R.Viswanathan,L.Madsen,J.Garnaes,D.K.Schwartz.Langmuir-Blodgett films.Science,1994,263(5154):1726-1733.
    [1] T. Hayashi, A. Yamamoto,Y. Ito, E. Nishioka, H. Miura, K. Yanagi. Asymmetric synthesis catalyzed by chiral ferrocenylphosphine transition-metal complexs. 8. Palladium -catalyzed asymmetric allylic amination. Journal of the American Chemical Society, 1989, 11 (16): 6301 -6311.
    [2] C.P. Andireux, C. Blocman, B. Dumas, J.M. Mhalla, F. Saveant. Determination of the lifetimes of unstable ion radicals by homogeneous redox catalysis of electrochemical reactions.Application to the reduction of aromatic halides. Journal of the American Chemical Society, 1980, 102(11): 3806 -3813.
    [3] J.S. Miller, A.J. Epatein. Recent advances in the structure-magnetic coulping relationships for metallocene-acceptor based electron transfer compiexes. NATO ASI Series, Series E: Applied Sciences, 1991, 198(Magn Mol. Mater): 151-158.
    [4] Y.C. Fann, H.S. Hao, R.C. Kapoor. Voltammetric study of ferrocene/ferricinium ion redox reactions in acetonitrile, Journal of the Chinese Chemical Society (Taipei,Taiwan), 1989, 36 (1): 21-24.
    [5] R. Bosque, C. Lopez, J. Sales. Substituent effects on the electrochemical behavior of iron(II) in Schiff bases derived from ferrocene and their cyclopalladated compounds. Inorganica Chimica Acta, 1996,244(1): 141-145.
    [6] T. Morikita, T. Yamamoto. Electrochemical determination of diffusion coefficient of π -conjugated polymers containing ferrocene unit. Journal of Organometallic Chemistry, 2001, 637-639: 809-812.
    [7] B.X. Ye, Y. Xu, F. Wang, Y. Fu, M.P. Song. Synthesis, structures and electrochemistry of two Schiff base compounds bearing phenylferrocene. Inorganic Chemistry Communications, 2005, 8(1): 44-47.
    [8] Z.X. Zhang, E.K. Wang. Electrochemical Theory and Technique. Science Press, Beijing, 2000.p. [9] A. Houlton, R.M.G. Roberts, J.Sliver. Studies on the antitumor activity of some iron sandwich compounds. J. Organomet. Chem., 1991,418(1): 107-112.
    
    [10] S. Petr, B. Tomas, C. Ivana. Synthesis and catalytic activity of spaced ferrocene oxazolines. Collect. Czech. Chem. Commun., 2003, 68: 1206-123.
    
    [11] G.C.A. Balavoine, G. Doisneau, T. Fillebeen, Khan. An improved synthesis of ferrocene -1, 1' -dicarboxaldehyde. J. Organomet. Chem., 1991,412(3): 381-382.
    [1]R.A.Durst,A.J.Baumner,R.W.Murray,R.P.Buck,C.P.Andrieux,Chemically modified electrodes:recommended terminology and definitions.Pure and Applied Chemistry,1997,69(6),1317-1323.
    [2]袁耀峰,叶素明,张蕴文,具有生物(理)活性的二茂铁衍生物.化学通报,1995,(5),24-31.
    [3]A.E.G.Cass,G.Davis,G.D.Francis,H.A.O.Hill,W.J.Aston,I.J.Higgins,E.V.Plotkin,L.D.Scott,A.P.F.Turner,Ferrocene-mediated enzyme electrode for amperometric determination of glucose.Analytical Chemistry,1984,56(4),667-671.
    [4]L.Gorton,H.I.Karan,P.D.Hale,T.Inagaki,Y.Okamoto,T.A.Skotheim,A glucose electrode based on carbon paste chemically modified with a ferrocene-containing siloxane polymer and glucose oxidase,coated with a poly(ester-sulfonic acid) cation-exchanger.Analytica Chimica Acta,1990,228(1),23-30.
    [5]朱邦尚,应太林,张晓岚,β—CD-1,1'二甲基二茂铁主客体葡萄糖生物传感器.上海大学学报(自然科学版),1999,5(4),353-537.
    [6]E.Laviron,General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems.Journal of Electroanalytical Chemistry and Interfacial Electrochemistry,1979,101(1),19-28.
    [7]Z.W.Zhu,N.Q.Li,Electrochemical studies of the interaction of 9,10-anthraquinone with DNA.1.Hanging mercury drop electrode.Microchemical Journal,1998,59(2),294-306.
    [1]江龙,以分子器件为背景的仿生膜.化学进腱,1994,6(3):195-208.
    [2]R Cea,C.Lafuente,J.S.Urieta,M.C.Lpeoz,F.M.Royo.Langmuir and Langmuir-Blodgett Films of a Viologen Derivative.Langmuir,1998,14(25):7306-7312.
    [3]P.Cea,C.Lafuente,J.S.Urieta,M.C.Lpeoz,F.M.Royo.Study and interpretation of the electrochemical behavior of some TTF derivatives.J.Eleetrochim.Acta,2000,46(4):589-597.
    [4]K.Wang,S.Mufioz,L.Zhang,R.Castro,A.E.Kaifer,G.Wgokel.Mechanism of Action of Vitamin B12.A New Test for Free Radical Intermediates Using a Cyclopropane Model for the Methylmalonyl-CoA to Succinyl-CoA Carbon Skeleton Rearrangement.J.Am.Chem.Soc.,1996,118(3):708.
    [5]R.Deschenaux,M.Schweissgnth,A.M.Levelut.Electron-transfer induced mesomorphism in the ferrocene-ferrocenium redox system:first ferrocenium-containing thermotropic liquid crystal.J.Chem.Soc.,Chem.Commun.,1996,(11):1275-1276.
    [6]L.M.Goldenberg,G.Cooke,M.C.Petty.Langmuir-Blodgett films of amphiphilic cyanovinyl ferrocene derivatives and their electrochemical behavior.Mater.Sci.Eng.,1998,C5(34):281-284.
    [7]黄量,于得泉.紫外光谱在有机化学中的应用(上册).北京:科学出版社,1988,22,130.
    [8]夏兵.单分子膜和LB膜制备、性质及应用.安徽大学硕士学位论文,2003,40-42.
    [9]W.X.Lu,W.H.Guo,H.L.Zhou,P.Sh.He.Component-Controllable Mixed Monolayer and Langmuir-Blodgett Films of Ru(dpphen)32+ and Arachidic Acid.Langmuir,2000,16(11):5137-5141.
    [10]J.T.Davies.The distribution of ions under a charged monolayer,and a surface equation of state for charged films.Proc.R.Soc.London,Ser.A,1951,208,224-47.
    [11]K.Sakakibara,H.Kamitakahara,T.Takano,F.Nakatsubo.Redox-active cellulose Langmuir-Blodgett films containing-carotene as a molecular wire.Biomacromolecules,2007,8(5):1657-1664.
    [12]L.M.Goldenberg,G.Cooke,M.C.Petty.Langmuir-Blodgett films of amphiphilic cyanovinyl ferrocene derivatives and their electrochemical behavior.Mater.Sci.Eng.C.,1998,C5(3,4):281-284.
    [13]K.Wohnrath,C.A.pessoa,RM.dos Santos,J.R.Garcia,A.A.Batista,O.N.Oliveira.Electrochemical properties of a ruthenium complex immobilized as thin films ang in carbon paste electrodes.Prog. Solid. State. Ch., 2005, 33 (3): 243-252.
    
    [14] M. Carter, M. Rodriguez, A.J. Bard. Voltammetric studies of the interaction of metal chelates with DNA. 2.Tris-chelated complexes of cobalt (III) and iron(II) with 1, 10-phenanthroline and 2, 2'-bipyridine. Journal of the American Chemical Society, 1989, 111(24): 8901-8911.

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