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羟基喹啉—二茂铁缩聚物及羟基喹啉—蛋氨酸的合成与性能研究
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摘要
8-羟基喹啉金属配合物与二茂铁聚合物是一类新型的功能材料,在光、电、磁等方面表现出许多特殊的性能,具有广泛的应用前景和重要的基础理论研究。为此,我们在分子设计和性能裁剪的思路上,合成了一系列的二茂铁型双(8-羟基喹啉)席夫碱高分子材料,并探索其结构与性能的关系。
     本课题研究中,以1,1′-二甲酰氯二茂铁与双(8-羟基喹啉)席夫碱为原料,按照分子设计和性能裁剪的思路,通过缩聚反应得到了二茂铁-8-羟基喹啉型缩聚物,再与不同金属离子M(Fe, Co, Ni, Cu等)配位,获得了一类新型的聚二茂铁-双(8-羟基喹啉)金属配合物。由于被配位的金属原子M和二茂铁中的铁原子间有一定的电子离域,这使它成为既含“磁性”基元的金属原子离域结构,又有“导电”基元的茂环和共轭取代基组成的大共轭体系的新一类高分子化合物。并且对8-羟基喹啉-二茂铁高分子材料采用元素分析、红外光谱(IR)、热重分析(TGA)、固体荧光光谱、X射线粉末衍射(XRD)、磁性分析等对聚合物的结构与性能进行了表征。
     研究结果表明,合成出的最终产物其化学结构基本符合预期结果,但结构相当复杂,产物中金属配位形式存在多种方式;限于目前的条件与技术水平,高聚物也尚难制成单晶,其化学结构及纯度并不十分明确。
     同时,我们还发现几个系列的化合物均具有较好的热稳定性,尤其是8-羟基喹啉—二茂铁型金属铜(Cu)聚合物的热稳定性。而金属配聚物较未配位金属的配体高温热稳定性提高不大,可能是由于金属离子与配体之间形成配位键的键能与配位体内的共价键键能相比要小得多,当金属配聚物受热裂解时,首先从配位键开始,因此对高温热稳定性的影响甚微。
     与无机物的XRD存在明显的尖锐峰不同,配合物(Fc-DD8Q-M)的XRD由于结晶很不完善,晶粒尺寸有限,因此其衍射峰由晶态衍射峰和非晶态的漫散射宽峰组成。配位聚合物的固体荧光测试表明化合物的发射谱出现在425~550nm之间,并且呈现三重荧光性质,在配体与金属离子配合后,荧光强度也有所增强,这可能是配位后体系的共轭程度增大,刚性增强的结果。
     磁性分析结果表明,在T=300K时,配体与金属配位聚合物的磁化率均大于零,且都在10-2~10-6数量级之间,说明配体和配合物在T=300K时为顺磁性材料;金属配位聚合物与配体相比较,矫顽力Hc,剩余磁化强度Mr都有增大了。我们认为这是由于过渡族金属Co为一种顺磁性粒子,而配体Fc-DD8Q作为一个弱Lewis碱,与过渡金属离子形成配合物,这样通过合理调控自旋中心间的耦合作用,使配体内部所含的铁Fe与配合金属Co之间产生相互交换作用。
     此外,对N-(8-羟基5-喹啉甲基)蛋氨酸锌配合物的合成与性能研究还处于探索阶段,许多测试工作还正在进行中,将为后续研究奠定基础。
Metal-coordination polymer containing 8-hydroxyquinoline and Ferrocenyl polymer served as a new class of functional polymer with lots of special electronic, electrochemical, optical and magnetic properties had extensive application prospects and important values in academic research. Then, on the basis of molecular designs and functional designs, we synthesized a series of metal-coordinated polymers based on ferrocenyl-dis(8-hydroxyquinoline schiff base), and its structures and some performances were studied too.
     In this paper, a novel compound of dis(8-hydroxyquinoline schiff base) containing ferrocenyl group was prepared by polycondensation between dis(8-hydroxyquinoline schiff base) and 1,1′-dichroloformyl- ferrocene by means of special molecular designs. Then metal-coordinated polymers containing ferrocenyl group and 8-hydroxyquinoline were obtained by self-assembly property. At the same time, because of certaining electronic delocalization between the coordinated metallic atom M (Fe, Co, Ni, Cu, et al) and the iron atom in the ferrocene, these polymeric compound contained both metallic atom delocalization structure of“magnetic”group and the great conjugated system consisted of cyclopentadienide ring and conjugated substituent of the“conductive”group. In the meanwhile, the structure and performance of the composite were characterized by means of elementary analysis, infrared absorption spectrum(IR), thermal gravimetry analysis(TGA), fluorescent spectroscopy, X-ray power diffraction method(XRD), and so on. And the magnetic properties of some compounds were studied under applied magnetic intensity in frequency 0~1.5GHz.
     Results showed that the final products were just the objects we wanted, but its chemical structures were comparatively complex, and many ways existed in the type of metallic coordinate linkage. We couldn’t ascertain their purity and chemical structure absolutely for the moment, because the polymer hardly cultivated single crystal restricted by our condition and technical level.
     Meanwhile, we found that all series of compounds were provided with fine thermal stability, especially metal(Cu)-coordinated polymers containing ferrocenyl group and 8-hydroxyquinoline. For the type compounds of dis(8-hydroxyquinoline schiff base) containing ferrocenyl group, the thermal decomposition temperature of 1,1’-divinylferrocenyl polymer could be enhanced by means of introducing dis-(8-hydroxyquinoline) group into the polymer. However, the thermal stability of metallic coordination polymer hardly enhanced in comparison with its ligands. It was possible that the energy of coordinate bond formed between metallic ion and polymer was trival in comparison with that of covalent bond in polymer. It started with coordinate bond when the coordinate polymer decomposed under high temperature, so it engendered little for the thermal stability at high temperature.
     The researches on X-ray diffraction showed metal-coordination polymers and its ligands took on minicrystal (microcrystalline) with short-range order, but its crystallinity was not quite ideal. Compared with spiculate diffraction peak of inorganic compound, X-ray diffraction of these compounds was formed by speculate crystalline diffraction peak and amorphous-state diffuse scattering peak.
     The emission fluorescence spectra of all the compounds ranged from 425nm to 550nm when excited by the light of maximal excitation wavelength(390nm) at the room temperature. Metal-coordination polymers and its ligands exhibited stronger solid tripartite-peaks fluorescence properties, and the fluorescence intensity of metal-coordination polymers got better improvement compared with that of its ligands. It might be that when its ligands was coordinated with another metallic atom M(Fe, Co, Ni, Cu), being formed new ring structure make molecule inflexibility better.
     The result of magnetic anlysis confirmed that magnetic susceptibility of all compounds is positive value, and its value ranged from 10-2 to 10-6. This is a proof that metal-coordination polymers and its ligands is paramagnetic complex at room temperature. Compared with that of its ligands, the coercive force and the remanence of metal-coordination polymers become stronger. The reason might be come from electron exchange of the coordinated metallic atom M (Fe, Co, Ni, Cu, et al) and the iron atom in the ferrocene.
     In addition, the researches on N-(8-hydroxy-5-quinolinemethyl) methionine zinc-coordinated complex are still at the exploratory stage, and lots of testing works are on the march which will lay the groundworks for continued studies.
引文
[1] 游效曾,孟庆金,韩万书. 配位化学进展[M]. 北京:高等教育出版社, 2000:318-321.
    [2] Segura J L. The chemistry of electroluminescent organic materials [J]. Acta. Polym., 1998,49:319-344.
    [3] 武霞, 刘云析, 朱道本,多功能有机及聚合物电致发光材料[J].高分子通报, 2000,2,39~46.
    [4] Pope M, Kallmann H P, Magnante P. Electroluminescence in organic crystals[J]. J. Chem. Phys., 1963,38(8):2042-2043.
    [5] Helfrich W, Schneider W G. Recombination radiation in anthracene crystals[J]. Phys. Rev. Lett., 1965,14(7): 229-232.
    [6] Vincett P S, Barlow W A, Hann R A, et al. Electrical conduction and low voltage blue electroluminescence in vacuum-deposited organic films[J]. Thin Solid Films, 1982,94:171.
    [7] 黄春辉,李富友,黄岩谊,光电功能超薄膜[M],北京:北京大学出版社(第一版), 2001:238.
    [8] Tang C W,Vanslyke S A.Organic electroluminescent diodes[J].Appl. Phys. Lett.,1987,51(12):913-915.
    [9] Greiner A.Design and synthesis of polymers for light emitting diodes[J].Poly. Adv. Technol.,1998,9(7):371-389.
    [10] Sheats J R,Chang Y L,Roitman D B,et a1.Chemical aspects of polymeric electroluminescent devices[J]. Acc. Chem. Ras.,1999,32(3): 193-200.
    [11] Muller C D, Falcou A, Reckefuss N. Multicolour organic light emitting displays by solution processing[J]. Nature, 2003, 421(6925): 829-833.
    [12] Hongsu Wang, Jiahui Huang, Shujie Wu, et al. Design and synthesis of Alq3-functionalized SBA-15 mesoporous material[J]. Materials Letters, 2006,60:26622665.
    [13] Adachi C, Tokiko S, Tsutsui T, et al. Electroluminescence in Organic Films with Three-Layer Structure[J]. Jpn. J. Appl. Phys., 1988, 27(2):269-271.
    [14] Tang C W, Vanslyke S A, et al. Electroluminescence of doped organic thin films[J], J. Appl. Phys., 1989, 65(9):3610-3616.
    [15] Aziz H,Popvic Z D,Hu N,et a1.Degradation mechanism of small molecular based organic light·-emitting devices[J] . Science , 1999 , 283(5409) :1900-1902.
    [16] Burroughes J H, Bradley D D C,Brown A R,et al. Light-emiting diodes based on conjugated Polymers[J]. Nature. 1990, 347(6294):539-541.
    [17] Gustafsson G,Cao Y,Treacy G M,et a1.Flexible light emitting diodes made from soluble conducting polymers[J].Nature,1992,357(6378):477-479.
    [18] Braun D, Heeger A J. Visibleli light emission from semiconducting polymer diodes[J]. Appl. Phys. Lett., 1991,58(18):1982-1984.
    [19] 张爱清,汪雨明,等.聚单己氧基萘乙炔(PEONV)的电致发光特性[J].功能材料,1998,29(6):632-634.
    [20] Zhiyong Hong, Daike Wang, et al. Synthesis and high efficiency green light-emiting diode of a soluble polymer[J]. Synthetic metals, 1997, 91:321-322.
    [21] Brand K L, Bentley P G, et al .Electroluminescent properties of a dialkoxy PPV derivatives[J]. Synthetic metals,1997,91:305-306.
    [22] Runguang Sun, Toshio Mascida, et al. Blue electroluminescence of polyacetylene derivatives[J]. Synthetic metals, 1997,91:301-303.
    [23] Braun D, Gustafsson G, et al. electroluminescence and electrical transport in poly(3-octylthiophene)[J]. J. Appl. Phys., 1992, 72(2):564-568.
    [24] Gebler D D, Wang Y Z, et al.,Blue electroluminescent devices based on soluble poly(P-pyridine)[J]. J. Appl. Phys., 1995, 78(6):4264-4266.
    [25] 黄春辉, 李富友, 黄岩谊. 光电功能超薄膜(第一版)M].北京:北京大学出版社, 2001:197-208&160-162.
    [26] 赵藻藩, 周性尧, 等. 仪器分析(第一版)[M].北京:高等教育出版社, 1992:160-161&158-160.
    [27] 陈国珍,黄贤智,等. 荧光分析法(第二版)[M].北京:科学出版社,1990:61-72.
    [28] 黄春辉,李富友,黄维. 有机电致发光材料与器件导论[M].上海:复旦大学出版社,2005:23-27.
    [29] Ballardini R, Varani G, T Indelli M, et al. Phosphorescent 8-quinolinol metal chelates. Excited-state properties and redox behavior[J]. Inorg. Chem., 1986, 25(22): 3858-3865.
    [30] Shao Y, Qiu Y, Hu M X, et al. A High Thermal Stable Light-Emitting Complex Based on a Tridentate Ligand[J]. Chem. Lett.,2000,29(9):1068-1069.
    [31] 李福绵译,功能高分子(第一版) [M]. 北京:科学出版社,1983: 81-88.
    [32] 李永忠, 陈泽堂, 周之荣,等. 5-(对羧基苯偶氮)-8-羟基喹啉与钍的显色反应及应用[J]. 南昌大学学报(理科版), 2004, 28(1): 92-95.
    [33] Kusakd E, Maeqawa K, Fukunaka Ninae M, et al. Two-liquid flotation of fine oxide particles with 8-hydroxyquinoline[J]. Can. J. Chem. Eng., 1999, 77(1): 62-68.
    [34] 朱昌青, 王伦, 李永新, 等. 鲁米诺-8-羟基喹啉-5-磺酸-镉(II)-过氧化氢化学发光体系研究[J].分析化学,1999,27(6):640-643.
    [35] 王征, 荆淼, 黎先春, 等. 8-羟基喹啉-硅胶介质的合成及其在海水中痕量铅检测的应用[J]. 分析化学, 2006, 36(4):459-463.
    [36] Hamaya T, Hiratani K, Ohashi K. Preparation of Water Soluble Polymer with 8-quinolinol Group and Its Specific Reactivity with Cd(Ⅱ)[J]. Chem. Lett., 1994,3:615-618.
    [37] Toshio T,Masatoshi K,Yasushi K,et a1.Soluble polymer complexes having A1q3-type pendent groups[J].Macromol. Rapid. Commun.,2004,24(12):1171-1174.
    [38] Meyers A, Weck M. Design and synthesis of Alq3-functionalized polymers[J]. Macromolecules, 2003, 36 (6):1766-1768.
    [39] Meyers A, South C, Weck M. Design, synthesis, characterization, andfluorescent studies of the first zinc-quinolate polymer[J].Chem. Comm., 2004, (10):1176-1177.
    [40] Meyers A, Weck M. Solution and solid-state characterization of Alq3-functionalized polymers [J]. Chem. Mater., 2004, 16(7):1183-1188.
    [41] 梅群波, 杜乃婴, 吕满庚. 含 8-羟基喹啉铝配合物的高分子聚合物的合成与表征[J]. 化学学报, 2004, 62(20):2113-2117.
    [42] 梅群波, 杜乃婴,梁利岩,等. 高相对分子质量 8 羟基喹啉锂聚合物的制备和性能[J]. 发光学报,2006,27(6): 1000-1006.
    [43] 胡芬, 刘承美, 雷国夫. 可聚合 8-羟基喹啉衍生物的合成及高分子化[J]. 高分子材料科学与工程, 2006, 22(2):100-103.
    [44] Gibson G K J, Packham D I. Chelating polymers derived from polyvinyl alcohol and cellulose[J]. J. Appl. Chem., 1966, 16:50-53.
    [45] 周建萍, 谭松庭, 赵斌,等. 高分子化 8-羟基喹啉锌配合物的制备与表征[J]. 湘潭大学自然科 学学报, 2001,23(4):74-77.
    [46] 余海湖,陈小幺,胡伟达,等. 高分子化 8-羟基喹啉及其 Cu(Ⅱ)配合物的制备与光谱性质[J]. 合成化学,2004,12(3):283-286.
    [47] Lu J P, Hlil A R, Meng Y Z, et al. Synthesis and characterization of a novel Alq3-containing polymer[J]. J. Poly. Sci.: Part A, 2000, 38(16): 2887-2892.
    [48] Xia X W, Lu J M, Li H, et al. Zn(II) based mixed complex with 8-hydroxyquinoline end group functionalized PSt and the study of fluorescent properties[J]. Optical Materials, 2005, 27:1350–1357.
    [49] 曾献谋, 余淑文, 徐仁贤. 中国科学院高分子学术会议会刊:高分子物理化学及物理研究工作报告会(1961)[C]. 北京: 科学出版社, 1963.
    [50] 谭松庭、周建萍,赵斌,等双 8-羟基喹啉-席夫碱-锌高分子配合物的制备及发光性能[J]. 发光学报,2003,24(1):51-55.
    [51] Xie J T, Fan L Q, Su J H, et al. Novel polymeric metal complexes based on bis-(8-hydroxylquinolinol)[J]. Dyes and Pigments, 2003, 59:153-162.
    [52] Sun Y C, Mierzwa J, Lan C R. Direct determination of molybdenum in seawater by adsorption cathodic stripping square-wave voltammetry[J].Talanta, 2000, 52(3):417-424.
    [53] Suzuki T. Chemical modification of PVC[J]. Pure. Appl. Chem., 1977, 49: 539-567.
    [54] Biswas M ,Moitra S. Synthesis and some properties of PVC-bound dimethylglyoxime complexes of Co(II), Ni(II), and Cu(II) [J]. J. Appl. Polym. Sci., 1989, 38(7): 1243-1252.
    [55] Moitra S, Biswas M. Thermal stability characteristics of some resins from chemically modified PVC [J]. J. Appl. Polym. Sci.,1989,37:1855.
    [56] Palma G, Carewza M. Degradation of poly(vinyl chloride). I. Kinetics of thermal and radiation-induced dehydrochlorination reactions at low temperatures[J]. J. Appl. Polym. Sci., 1970,14:1737.
    [57] Adachi C, Tokito S, Tsutsui T, Saito S. Blue lighting-emitting organic electroluminescent devices[J]. Appl. Phys. Lett., 1989,56(9):799-781.
    [58] Adachi C.Tsutsui T,Saito S.Blue light-emitting organic electroluminescent devices [J].App1. Phys. Lett.,1990,56(9):799-801.
    [59] Kido J, Hongawa K, Kohda M, Nagai K, Okayama K. Molecularly Doped Polymers as a Hole Transport Layer in Organic Electroluminescent Devices[J]. Jpn. J. Appl. Phys., 1992,31(7B): L960-L962.
    [60] Chiang C K, Fincher C R, Park J W , et al. Electrical conductivity in doped polyacetylene[J]. Phys. Rev. Lett., 1977, 39:1098.
    [61] Pei Q B, Yu G, Zhang C, et a1. Polymer light-emitting electrochemical cells[J]. Science, 1995, 269: 1086.
    [62] Pei Q B,Yang Y,Yu G,et a1.Polymer light-emitting electrochemical cell:in situ formation of a light-emitting p-n junction[J].J. Am. Chem. Soc.,1996,118:3922.
    [63] Thakur M. A class of conducting polymers having nonconjugated Backbones[J]. Macromolecules, 1988,21: 661-664.
    [64] Thakur M, Elman B S. Optical and magnetic properties of a nonconjugated conducting polyer[J]. J. Chem. Phys.,1989,90(3):2042-2044.
    [65] Shang Q Y, Pramanick S, Hudson B.Chemical nature of conduction in iodine-doped trans-1,4-poly(buta-1,3-diene) and some of its derivatives: the presence of I3- and the effect of double-bond configuration[J]. Macromolecules, 1990, 23(6):1886-1889.
    [66] Kealy T J, Pauson P L. A new type of organo-iron compound[J]. Nature,1951, 168:1039.
    [67] Wilkinson G,Woodward R B. The structure of iron bis-cyclopentadienyl[J].J. Am. Chem. Soc.,1952, 74:2125-2126.
    [68] Gonsalves K, Lin Z R , Rausch M D.The Cationic polymerization and copolymerizatin of isopropenylmetallocene monomers[J].J. Polym. Sci. Chem. Ed.,1985,23:1707.
    [69] Arimoto F S,Haven A C. Derivatives of dicyclopentadienyliron[J]. J. Am. Chem. Soc.,1955,77:6295-6297.
    [70] 林展如.金属有机聚合物[M].成都:成都科技大学出版社,1987,1-4&266-304
    [71] Neuse E W,Bednarik L. The organolithium organohalide coupling reaction as a synthetic route to poly (1,1'-ferrocenylenes) [J].Macromolecules,1979,12:187-195.
    [72] Pittman C U,Jr J. Synthesis of ferrocene-containing poly(phosphine oxide) and poly(phosphine sulfides)[J]. J. Polym. Sci.:Part Al,1967,5:2927-2937
    [73] Neuse E W,Chris G J.Poly(ferrocenylphosphine oxides) [J].J. Macromol. Sci. Chem.,1967,A-1:371-386.
    [74] Frederick L H , Rosenberg H. Oxidation-resistant metallocenes :Decachloroferrocene and related polychlorinated ferrocenes[J].J. Am. Chem. Soc.,1970,92(10):3239-3240.
    [75] Kunitake T , Nakashima T , Aso C. Syntheses and reactions of ferrocene-containing polymers III Cyclopolymerization of 1,1’-divinyl ferrocene[J]. J. Polym. Sci.:Part A-1,1970,8:2853-2859.
    [76] Toseihide A , Yoyoki U , Chuji A.Syntheses and Reactions of Ferrocene-Containing Polymers V Polymerization of Ethinylferrocene[J].Die.Makromlekulare. Chem.,1972,157:73-85.
    [77] Gonsalves K,Lin Z R,Rausch M D. Ferrocene-containing polyamides and polyureas[J]. J. Am. Chem. Soc.,1984,106:3862-3863.
    [78] Foucher D A,Tang B Z,Manners I. Ring-opening polymerization of strained,ring-tilted ferrocenophanes : a route to high molecular weight poly(ferrocenylsilanes)[J]. J. Am. Chem. Soc.,1992,114:6246-6248.
    [79] 王学杰,王立,王建军.高分子量聚二茂铁衍生物的性质与应用[J].功能高分子学报,2002,15:268-376.
    [80] 唐红定,秦金贵.聚二茂铁硅烷的合成与性能[J].高分子通报,2001,4:15-23.
    [81] 王立,潘杰,计兵,等.热开环聚合制备高分子量二茂铁基聚二甲基硅烷及其与四氰基乙烯生成电荷转移络合物的研究[J].高分子学报,2000,6:788-790.
    [82] Yamamoto T,Morikita T,Maruyama T,et al..Poly(aryleneethynylene) type polymers containing a ferrocene unit in theπ-conjugated main chain ,preparation,optical properties,redox behavior,and Mossbauer spectroscopic analysis[J].Macromolecules,1997,30:5390-5396.
    [83] Southard G E,Curtis M D. Poly(3,3'-dihexyl-4,4'-dimethyl -1,1'-ferrocenylene -1,4'-phenylene) and poly(3,3'-dihexyl-4,4'-dimethyl -1,1'-ferrocenylene-2,5'-thienylene) [J]. Organometallics,1997,16:5618-5620.
    [84] 陈秋玲,林展如. 间苯二甲酰二茂铁二乙酰腙金属(Cu、Co、Ni)配位聚合物的高频介电性能[J].四川师范大学学报(自然科学版),2000,23:500-504.
    [85] 彭华侨,安全长,蒋福全,等.两种可溶性二甲酰二茂铁酰胺缩聚物的合成与表征[J].四川师范大学学报(自然科学版),2004,27:391-394
    [86] Mohamed M, ABD-ALLA, Maher F, et al. Arylidene Polymers XVIII Synthesis and Thermal Behavior of Organometallic Arylidene Polyesters Containing Ferrocene Derivatives in the Main Chain[J].J. Appl. Poly. Sci.,1993,47:323-329.
    [87] 林云,干久志,林展如.二茂铁 Schiff 碱缩聚物的合成与表征[J].四川师范大学学报(自然科学版),1998,21:540-544.
    [88] Hiroshi I,Yuji S,Yukiyasu K,et al. Long-Lived Charge-Separated State Generated in a Ferrocene-meso, meso-Linked Porphyrin Trimer-Fullerene Pentad with a High Quantum Yield[J].Chem. Eur. J.,2004,10:3184-3196.
    [89] Julie B,Thomas B,Bertrand D,et al. Ferrocene-Containing Optically Active Liquid-Crystalline Side-Chain Polysiloxanes with Planar Chirality[J].Adv. Funct. Mater.,2006,16:260-267.
    [90] Akhter Z,Mubasher,Bashir A,et al. Synthesis,characterization and thermal degradation kinetics of ferrocene-containing aramids[J].Appl. Organometal. Chem.,2005,19:848-853.
    [91] Ahmed I,David F. Preparation and characterisation of tractable regioregular head-to-tail poly(3-alkylthiophene)s with ferrocene substituents[J].Polym. Int.,2006,55:780-783.
    [92] 王学杰.二茂铁基聚合物的合成和性能研究.[D]浙江.浙江大学,2005
    [93] Hmyene M , Yasser A , Escorne M , et al. Magnetic-properties of ferrocene-based conjugated polymer[J].Adv. Mater.,1994,6:564-567.
    [94] 陈涛.线型及支化二茂铁基聚合物的合成、自组装及性能研究.[D]浙江.浙江大学,2006.
    [95] 林展如.磁性高分子及其应用[A].何天白,胡汉杰.功能高分子与新技术[M].北京:化学工业出版社,2001,86-94.
    [96] 林展如,倪训铭.宽温低磁损金属有机磁性材料的制造方法[P].中国发明专利: 91110991.9,1993.
    [97] Lin Z R,Yu Z P,Hu H J. Syntheses and properties of diacetylferrocene acylhydrazone polycondensates[J]. Progress in Nature Science,1999,9:760-766.
    [98] Lin Z R,Ni X M,Hu H J. Novel metallocene-containing polymers and their unusual ferromagnetic properties[J].Progress in Nature Science,1996,6:120-124.
    [99] 干久志,林云,林展如.轻质金属有机高分子吸波剂(OPA)及其 RAM 的性能研究[J].功能材料,2001,32(5):456-457.
    [100] Wang H S, Huang J H, Wu S J, et al. Design and synthesis of Alq3-Functionalized SBA-15 Mesoporous material[J]. Material Letters, 2006, 60:2662-2665.
    [101] Miller J S, Epstein A J. Ferromagnetic molecular charge-transfer complex[J]. Chem. Rev., 1988, 88:201-203.
    [102] Sugano T, Nomura M, Awaga K, et al. Magnetism, electronic state and local structure of iron-containing organometallic polymers[J]. Bull. Chem. Soc. J.,1986,59:2615-2621.
    [103] Palacio F,Moron M C, Garin J, et al.Ferromagnetic interactions above room temperature in a Schiff-base metal-organic polymer[J]. Mol. Cryst. Liq. Cryst.,1989,176:415-422.
    [104] Vernios M,Williams M.Copolymers of 3,3′,4,4′tetraamino-biphenyl and 1,2,4,5 tetraaminobenzene with 1,1′bis(glyxalyl) ferrocene and 1,1′bis(phenylglyoxaly) ferrocene[J]. J. Appl. Polym. Sci., 1979, 23:1601-1605.
    [105] Francio G, Abderrahim Y. Conjugated polymers containing metallocene groups oxidizable to ferromagenetic materials[P], C. A., 1993, 118: 60314V.
    [106] Lin Z R.Organomegtallic polymers with ferromagnetic properties[J].Adv. Mater.(special issue),1999,11(13):1153-1155.
    [107] Lin Zhanru . A novel ambient temperature stable organometallic ferromagnet[A] . Proc of the 2nd lntern Symp on Physics of Magnetic Materials[C],Beijing,1992.1:191-193.
    [108] Clemo G R, Howe R. 5-formyl-8-hydroxy-quinoline[J]. J. Chem. Soc., 1955, 3552-3553.
    [109] 周建萍.高分子化 8-羟基喹啉金属配合物的制备及其发光性能的研究. [硕士学位论文]湖南.湘潭大学,2002.
    [110] 任引哲,王玉湘.物质的颜色与结构[M]. 北京:北京师范大学出版社,1991:56-68&103-129.
    [111] Rosenblum M,Woodward R B. The structure and chemistry of ferrocene III evidence pertaining to the ring rotational barrier[J].J. Am. Chem. Soc.,1958,8:5443-5449.
    [112] 金培嵩,李峰,赵刚,等.二茂铁芳酰基腙与一些过渡金属的鳌合物[J]. 兰州大学学报(自然科学版),1991,27:55-57.
    [113] 徐 红 , 曹 振 宇 , 桑 雅 丽 , 等 . 手 性 二 茂 铁 基 氨 基 酸 配 合 物(S)-[Zn(FcCH2NHCH(CH2Ph)COO)2·H2O](H2O)的合成及性能[J]. 无机化学学报,2006,22(8):1438-1442.
    [114] 焦剑,雷渭媛. 高聚物结构、性能与测试[M]. 北京: 化学工业出版社,2003:727-737.
    [115] 顾振军,王寿泰 . 聚合物的电性和磁性 [M].上海:上海交通大学出版社,1990,293-311.
    [116] 邢丽英.隐身材料[M]. 北京:化学工业出版社,2004:1-96.
    [117] 郭瑞萍. 国外陆军隐身技术发展主力[J]. 国外兵器动态,2000,4:1-3.
    [118] Courric S, Tran V H.The electromagnetic properties of blends of poly (p-phenylene-vinylene) derivatives[J]. Polymers for Advanced Technologies, 2000, 11(6):273-279.
    [119] 李瑞琦,何世禹,初文毅.吸波涂层材料研究进展[J]. 兵器材料科学与工程, 2006, 29(3):76-80.
    [120] 王少敏,高建平,于九皋,等.大分子视黄基席夫碱盐微波吸收剂的制备[J].宇航材料工艺,2000,2:51-54.

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