含吡啶基团共轭富硫化合物合成及性质研究
详细信息    本馆镜像全文|  推荐本文 |  |   获取CNKI官网全文
摘要
四硫富瓦烯(tetrathiafulvalene, TTF)衍生物和二硫纶(dithiolene)衍生物等富硫化合物作为有机光、电、磁的功能化合物,一直受到人们的关注。近年来,利用富硫有机给体与过渡金属离子的结合形成有机/无机杂化材料,在富硫化合物领域已经成为研究的热点之一。本论文基于具有含氮配位基团的TTF衍生物和二硫纶化合物,研究该类具有氧化还原和金属配位双功能化合物的性质。论文的工作主要包括以下几个方面:
     一、综述部分简要介绍了TTF衍生物的性质及研究进展,描述了具有氧化还原功能的TTF-Py类衍生物的研究现状。同时,还介绍了二硫纶衍生物的性质及研究进展,对含d8结构金属的二硫纶配合物的最新进展作了概括。
     二、合成了2,3-dimethylthio-6-pyridyl-tetrathiafulvalene, DMT-TTF-Py,以DMT-TTF-Py为研究对象,通过电化学性质和紫外-可见光谱的方法研究了该化合物与质子之间的相互作用,并得到了该配体与强酸、弱酸不同结合方式的两个化合物的晶体,并测定和分析了它们的结构。
     三、合成了4-pyridin-4-yl-(1,3) dithiol-2-one, PYDO,并以PYDO为配体设计、得到了三个金属配合物,通过单晶衍射测定了三个配合物的结构,并研究了它们不同的配位方式。
     四、以PYDO为配体合成了一个新的含吡啶基团的镍二硫纶配合物。通过电化学、紫外-可见吸收光谱的变化,研究了镍二硫纶配合物的氧化还原性质、对质子的响应,从而得出该配合物与质子的结合/解离平衡和氧化/还原平衡的关系。并合成了该配合物与酸的两个质子化合物,测得了它们的晶体结构。
Tetrathiafulvalene (TTF) and dithiolene derivatives have been widely studied in the research fields of material chemistry and supramolecular chemistry, because they exhibit optical, electronic and magnetic properties. Great interest is currently devoted to obtain organic/inorganic hybrid materials that combine the sulfur-rich organic donors with the transition-metal ions. In this work new TTF and dithiolene derivatives, which directly conjugated with pyridine group and have both redox property and metal coordination property, were synthesized and characterized. The major studies are as follows:
     1、In introduction, the properties and important achievements of TTF derivatives are reviewed briefly. Recent researches on TTF-Py with redox properties are summarized. At the same time, the dithiolene derivatives are described, Then the new progresses of d8 metal dithiolenes are summarized.
     2、New compound 2,3-dimethylthio-6-pyridyl-tetrathiafulvalene, DMT-TTF-Py, has been synthesized for research. Electrochemical responses of the compound to H+ cation and the corresponding UV-vis-NIR spectra have been studied. Crystal of two protonated salts were prepared. Structures of the them have been determined by single crystal X-ray diffraction.
     3、Three metal complexes of 4-pyridin-4-yl-(1,3) dithiol-2-one, PYDO have been designed and synthesized. The structures of these complexes have been characterized by single crystal X-ray diffraction. The coordination behaviors of the ligand and the intermolecular interactions of the compounds have been studied.
     4、A nickel dithiolene complex of PYDO have been synthesized and characterized. Electrochemical responses of the compound to H+ cation and the corresponding UV-vis-NIR spectra have been studied. Their redox and coordination behaviors were also studied by electrochemical and spectral analysis. The structures of two protonated compounds have been determined by single crystal X-ray diffraction.
引文
[1] Bryce M. R, Chem. Soc. Rev. 1991, 20, 355.
    [2] Schukat G, Fanghanel E. Sulfur. Rep. 1993, 14, 245.
    [3] Sinzger k., Hünig S., Jopp M., et al. J. Am. Chem. Soc.1993, 115,7696.
    [4] Mallah T., Thiebaut S., Verdaguer M. Science 1993, 262,1551.
    [5] Jiang M, Fang Q. Adv. Mater. 1999, 11, 1147.
    [6] Geiser U, Schlueter J. A., Wang H. H. J. Am. Chem. Soc. 1996, 118, 1996.
    [7] aquel Andreu, Isabelle Malfant, Pascal G.Lacroix, Patrick Cassoux, Eur.J.Org.Chem. 2000, 737.
    [8] J. M. Williams, J. R.Ferraro, R. J.Thorn, K. D.Carlson, U.Geiser, H. H.Wang, A. M.Kini, M.-H.Whangbo, Organic Superconductors (Including Fullerenes); Prentice Hall, Englewood Cliffs, N J, 1992.
    [9] Kryschenko Y. K, Seidel S. R., Muddiman D. C. J. Am. Chem. Soc. 2003, 125, 9647.
    [10] Zhang Y. G, Li J. M, Chen J. H. Inorg. Chem. 2000, 39, 2330.
    [11]李胜利,吴杰颖,马文,配位聚合物的设计合成与性质研究[J]安徽大学,报:自然科学版, 2004, 28, 56
    [12] Desiraju G. R, The Crystal as a Supramolecular Entity, Wiley, Chichester, 1995.
    [13] (a) Williams J. M., Ferraro J. R, Thorn R. J, Carlson K. D, Geiser U, WanH. H.,Kini A. M, Whangbo M.-H. Organic. Superconductors (Including Fullerenes) Synthesis, Structure, Properties, and Theory; Prentice Hall: Englewood Cliffs, N J, 1992; (b) Ishiguro T, Yamaji K, Saito G, Organic Superconductors; Springer-Verlag: New York, 1998.
    [14] (a) Novoa J. J, Rovira M. C, Rovira C, Veciana J, Tarrés J. Adv. Mater.1995, 7, 233; (b) Rovira C, Novoa J. Chem. Eur. J. 1999, 5, 3689
    [15] (a) Ishiguro T, Yamaj K i, Saito G.Organic Superconductors; 2nd ed;Berlin 1998; (b) Coronado E, Day P. Chem. Rev. 2004, 104, 5419
    [16] (a)Liu S.-X, Dolder S, Franz P, Neels A, Stoeckli-Evans H, Decurtins S. Inorg. Chem. 2003, 42, 4801; (b) Setifi F, Ouahab L, Golhen S, Yoshida Y, Saito G. Inorg.Chem. 2003, 42, 1791.
    [17] Iwahori F, Gohlen S, Ouahab L, Carlier R, Sutter J.-Inorg. Chem. 2001, 40, 6541.
    [18] Coffe D. L, Chambers J. Q., Williams D. R. J. Am. Chem. Soc. 1971, 93, 2258.
    [19] Cooleman L. B. Solid State Commun. 1973, 12, 1125.
    [20] Setifi F, Ouahab L, Golhen S., Yoshida Y, Saito G. Inorg.Chem. 2003, 42, 1791
    [21] HervéK, Gal Y. L, Ouahab L, Golhen S, Cador O. Synth. Met. 2005, 153, 461.
    [22] Hai Xue, Xin-Jing Tang, Li-Zhu Wu, Li-Ping Zhang, and Chen-Ho Tung, J. Org. Chem. 2005, 70, 9727
    [23] Liu S-X., Dolder S., Pilkington M, Decurtins S. J. Org. Chem. 2002, 67, 3160.
    [24] Liu S-X, Dolder S., Franz P., Neels A., Stoeckli-Evans H, Decurtins S. Inorg. 2003, 42, 4801.
    [25] Campagna S, Serroni S, Puntoriero F, Cola L. D,Kleverlaan C. J, Becher J, Hascoat P, Thorup N. Chem. Eur. J. 2002, 8, 19.
    [26] Devic T, Avarvari N, Batail P, Chem. Eur. J. 2004, 10, 3697.
    [27] Devic T, Rondeau D., Sahin Y., Levillain E, Cl′erac R, Bataila P, Avarvari N. J. Chem. So., Dalton Trans. 2006, 1331.
    [28] Wang L, Zhang B, Zhang. J. Inorg. Chem. 2006, 45, 6860.
    [29] Liu Y, Zhu Q-Y, Dai J, Zhang Y, Bian G-Q, Lu W. J. Coord. Chem. 2007, 60, 2319
    [30]Hunig S., Kiesslich G., Quast H, et al, Liebigs Ann.Chem. 1973, 310.
    [31]Wudl F., Smiss G.M.,Hunfnagel E.J, J.Chem.Soc.Chem.Commun. 1970,1453.
    [32]Mallah T, Thiebaut S., Verdaguer M, et al., Science, 1993, 262, 1551
    [33] Sinzger K, Hünig S, Jopp M,et al, J.Am. Chem. Soc., 1993, 115, 7696
    [34]潘庆才,彭正和,二硫纶配合物和聚合物体系的分子设计及功能性的探讨.河南科学, 2001, 19, 46
    [35] Akiko Kobayashi, Emiko Fujiwara, and Hayao Kobayashi Chem. Rev. 2004, 104, 5243
    [36] Ste′phane A. Baudron, Narcis Avarvar i, and Patrick Batail Inorg. Chem. 2005, 44, 3380
    [37] Nora Lardie, Elena Cerrada *, Mariano Laguna Polyhedron 2006, 25, 2785
    [38] Vedichi Madhu and Samar K. Das Inorganic Chemistry, 2008, 47, 5055
    [39] Josephine M. Tunney, Alexander J. Blake, E. Stephen Davies, Jonathan McMaster, Claire Wilson, C. David Garner Polyhedron 2006,25, 591
    [40] McCleverty, J. A. Prog. Inorg. Chem. 1968, 10, 49.
    [41] Yanli Feng, Qiong Zhang, Wenjuan Tan, Deqing Zhang, Yaoquan Tu, Hans He Tian, Chemical Physics Letters 2008, 455, 256
    [42] Jincai Wu, Nathalie Dupont, Shi-Xia Liu, Antonia Neels, Andreas Hauser, and Silvio Decurtins Chem. Asian J. 2009, 4, 392
    [43] Qin-Yu Zhu, Yu Liu, Wen Lu, Yong Zhang, Guo-Qing Bian, Gai-Yan Niu, and Jie Dai, Inorganic Chemistry, 2007, 46, 10065
    [44] Lei Yu, Qin-Yu Zhu, Yong Zhang, Zhi-Xin Lei, Gai-Yan Niu, and Jie Dai J. Phys. Chem. A, 2008, 112, 13672
    [1] (a) Iwahori F, Gohlen S, Ouahab L, Carlier R., Sutter J.-P. Inorg.Chem. 2001, 40, 6541; (b) Setifi F, Ouahab L, Golhen S, YoshidaY, Saito G. Inorg. Chem. 2003, 42, 1791; (c) Ouahab L, Iwahori F, Golhen S, Carlier R, Sutter J.-P. Synth. Met. 2003, 133-134, 505; (d) HervéK, Gal Y. L, Ouahab L, Golhen S, Cador O. Synth. Met. 2005, 153, 461.
    [2] (a) Liu S.-X, Dolder S, Franz P, Neels A, Stoeckli-Evans H., Decurtins S. Inorg. Chem. 2003, 42, 4801; (b) Jia C.-Y, Liu S.-X, Ambrus C, Neels A, Labat G, Decurtins S. Inorg. Chem. 2006, 45, 3152.
    [3] Devic T, Avarvari N, Batail P. Chem. Eur. J. 2004, 10, 3697.
    [4] (a) Xu W, Zhang D.-Q, Li H, Zhu D.-B. J. Mater. Chem. 1999, 9, 1245; (b) Goldenberg L. M, Becker J. Y, Levi O. P.-T, Khodorkovsky V. Y, Bryce M. R, Petty M. C. J. Chem. Soc. Chem. Commun. 1995, 475; (c) Levi O. P.-T., Becker J. Y, Ellern A, Khodorkovsky V. Y. Tetrahedron Lett. 2001, 42, 1571; (d) Griffiths J.-P, Brown R. J, Day P, MatthewsC. J, Vital B, Wallis J. D. Tetrahedron. Lett. 2003, 44, 3127; (e) Jia C., Zhang D, Xu Y, Xu W, Hu H, Zhu D. Synth. Met. 2003, 132, 249.
    [5] (a) Iyoda M., Kuwatani Y., Ueno N., Oda M. J. Chem. Soc. Chem. Commun. 1992, 158; (b) Moore J., Batsanov A. S., Bryce M. R, Howard J. A. K, Khodorkovsky V, Shapiro L, Shames A. Eur. J. Org. Chem. 2001, 73.
    [6] Andreu R, Malfant I, Lacroix P. G., Cassoux P. Eur. J. Org. Chem. 2000, 737.
    [7] Liu S.-X., Dolder S., Pilkington M., Decurtins S. J. Org. Chem. 2002, 67, 3160.
    [8] (a) Campagna S, Serroni S, Puntoriero F, Loiseau F, De Cola L, Kleverlaan C. J, Becher J, Sorensen A. P, Hascoat P, Thorup N. Chem. Eur. J. 2002, 8, 4461; (b) Bouguessa S, Herv K, Golhen S, Ouahab L, Fabre J.-M. New J. Chem. 2003, 27, 560; (c) Liu S.-X, Dolder S, Rusanov E. B, Stoeckli-Evans H, Decurtins S, Acad C. R. Sci. Chimie. 2003, 6, 657.
    [9] (a) Iwahori F, Gohlen S, Ouahab L, Carlier R, Sutter J.-P. Inorg. Chem. 2001, 40, 6541; (b) Setifi F, Ouahab L, Gohlen S, YoshidaY, Saito G. Inorg. Chem. 2003, 42,1791; (c) Ouahab L., Iwahori F, Gohlen S, CarlieR. r, Sutter J.-P. Synth. Met. 2003, 133-134, 505; (d) HervéK., Gal Y. L, Ouahab L., Golhen S, Cador O, Synth. Met. 2005, 153, 461.
    [10] (a) Levi O. P.-T, Y. Becker J, Ellern , Khodorkovsky V. Y. Tetrahedron Lett. 2001, 42, 1571; b) Jia, C.-Y Zhang D.-Q, Xu Y, Xu W, Hu, H. Zhu D.-B. Synth. Met. 2003, 132, 249.
    [11] Andreu R, Malfant I, Lacroix P. G, Cassoux P, Eur. J. Org. Chem. 2000, 737.
    [12] Xue H, Tang X.-J, Wu L-Z, Zhang L-P, Tung Ch-H. J.Org.Chem. 2005 70, 9727.
    [13] Wang L, Zhang B, Zhan J-p. Inorganic Chemistry 2006, 45, 6860.
    [14] Benbellat N, Le Gal Y, Golhen S, Gouasmia A, Ouahab L, M.Fabre J. Eur.J.Org.Chem. 2006, 4237.
    [15] Wang L, Zhang B, Zhang. J. Inorg. Chem. 2006, 45, 6860
    [16] (a) Kurmoo M., Graham A. W, Day P, Coles S. J., Hurthouse M. B, Caulfield J. L, Singleton J., Pratt F. L, Hayes W, Ducasse L, Guinneau P. J. Am. Chem. Soc. 1995, 117, 12209; (b) Coronado E, Galan-Mascaros J. R, Gomez-Garcia C. J. Laukhin V, Nature 2000, 408, 447.
    [17] Mas-Torrent M, Turner S. S, Wurst K, Vidal-Gancedo J., Ribas X, Veciana J, Day P, Rovira C. Inorg. Chem. 2003, 42, 7544.
    [18] Otkrytiya, Izobret, Prom. Obraztsy, Tovarnye Znaki 1980, 5, 75(Russian).
    [19]迟兴宝,李小平,双(6,7-二甲硫基四硫富瓦烯-2,3-二硫)金属配合物的合成[J],合成化学,2002,10(4),366。
    [20] O. Paz-Tal Levi, J. Y. Becker, A. Ellern, V. Khodorkovsky. Tetrahedron Letters, 2001, 42, 1571.
    [21] (a) Reviews on TTF applications: Segura J. L, Martin N, Angew. Chem., Int. Ed. 2001, 40, 1372; (b) Brondstet Nielsen M, Lomholt C, Becher J, Chem. Soc. Rev. 2000, 29, 153.
    [22] Qin-Yu Zhu, Yu Liu, Wen Lu, Yong Zhang, Guo-Qing Bian, Gai-Yan Niu, and Jie Dai, Inorganic Chemistry, 2007, 46, 10065.
    [23] (a) Lin, H.-H; Yan, Z.-M; Dai, J; Zhang, D.-Q; Zuo, J.-L; Zhu,Q.-Y; Jia, D.-X.New J. Chem. 2005, 509. (b) Zhu, Q.-Y; Lin,H.-H; Dai, J; Bian, G.-Q; Zhang,Y;Lu, W. New J. Chem. 2006, 1140.
    [24] (a) A. Mamedov, J. Ostrander, F. Aliev, N. A. Kotov, Langmuir, 2000, 16, 3941; (b) T. Cassagneau, F. Guerin. J. H. Fendleer, Langmuir, 2000, 16, 7318; (c) M. Schutte, D. G. Kurth, M. R. Lindford, H. Colfen, H. Mohwald, Angew.Chem. Int. Ed. 1998, 37, 2891.
    [25] Qin-Yu Zhu, Yu Liu, Wen Lu, Yong Zhang, Guo-Qing Bian, Gai-Yan Niu, and Jie Dai, Inorganic Chemistry, 2007, 46, 10065.
    [1] (a)Liu S.-X, Dolder S,. Franz P, Neels A, Stoeckli-Evans H, Decurtins S. Inorg. Chem. 2003, 42, 4801; (b) Setifi F., Ouahab L, Golhen S, Yoshida Y, Saito G.. Inorg. Chem. 2003, 42, 1791
    [2] Kobayashi A., Fujiwara E, Kobayashi H. Chem. Rev. 2004, 104, 5243.
    [3] (a) FourmiguéM, Batail P. Bull. Soc. Chim. Fr. 1992, 129, 29; (b)FourmiguéM., Uzelmeier C. E, Boubekeur K, Bartley S. L, Dunbar K. R. J. Organomet. Chem. 1997, 529, 343; (c) Uzelmeier C. E, Bartley S. L, FourmiguéM, Rogers R., Grandinetti G, Dunbar K. R. Inorg. Chem. 1998, 37, 6706; (d) Avarvari N, Martin D., FourmiguéM. J. Organomet. Chem. 2002, 292, 643; (e)Devic T, Batail P, FourmiguéM, Avarvari N. Inorg. Chem. 2004, 43, 3136; (f) Avarvari N, FourmiguéM. Chem. Commun. 2004, 1300.
    [4] Smucker B. W, Dunbar K. R. J. Chem. Soc, Dalton Trans. 2000,1309.
    [5] Cerrada E, Diaz C., Diaz M. C, Hursthouse M. B, Laguna M,Light M. E. J. Chem. So., Dalton Trans. 2002, 1104.
    [6] Pellon P, Gachot G., Le Bris J, Marchin S, Carlier R, Lorcy D. Inorg. Chem. 2003, 42, 2056.
    [7] Ga?lle T., Franck L. D., Jo?l L., Miloud M., Jean R., Alain G., Eric L., Marc S. Chem. Eur. J. 2004, 10, 6497.
    [8] Tomoyuki A., Keiko K., Tatsuo H., Takayoshi N., Christian A., Christensen J. B. Langmuir 2004, 20, 4187.
    [9] Adrian J. M, Leonid M., Martin R. Bryce M, Petty C, Andrew P, Claudia M, Jack Y, Malcolm J. J, Simon N. P. Adv. Mater. 1998, 10, 395.
    [10] (a) Iwahori F, Gohlen S, Ouahab L, Carlier R, Sutter J.-P. Inorg.Chem. 2001, 40, 6541; (b) Setifi F, Ouahab L, Golhen S, Yoshida, Saito G. Inorg. Chem. 2003, 42, 1791; (c) Ouahab L, Iwahori F, Golhen S, Carlier R, Sutter J.-P. Synth. Met. 2003, 133, 505; (d) HervéK, Gal Y. L, Ouahab L, Golhen S, Cador O. Synth. Met. 2005, 153, 461.
    [11] (a) Liu S.-X., Dolder S, Franz P., Neels A, Stoeckli-Evans H, Decurtins S.Inorg. Chem. 2003, 42, 4801; (b) Jia C.-Y., Liu S.-X., Ambrus C., Neels A., Labat G., Decurtins S. Inorg. Chem. 2006, 45, 3152.
    [12] Devic T, Avarvari N, Batail P. Chem. Eur. J. 2004, 10, 3697.
    [13] (a) Xu W., Zhang D.-Q, Li H, Zhu D.-B. J. Mater. Chem. 1999, 9, 1245; (b) Goldenberg L. M., Becker J. Y, Levi O. P.-T, Khodorkovsky V. Y, Bryce M. R, Petty M. C. J. Chem. Soc. Chem. Commun. 1995, 475; (c) Levi O. P.-T, Becker J. Y, Ellern A, Khodorkovsky V. Y. Tetrahedron Lett. 2001, 42, 1571; (d) Griffiths J.-P, Brown R. J, Day P, MatthewsC. J, Vital B, Wallis J. D. Tetrahedron. Lett. 2003, 44, 3127; (e) Jia C, Zhang D, Xu Y, Xu W, Hu H, Zhu D. Synth. Met. 2003, 132, 249.
    [14] (a) Iyoda M, Kuwatani Y., Ueno N, Oda M. J. Chem. Soc. Chem. Commun. 1992, 158; (b) Moore J, Batsanov A. S, Bryce M. R, Howard J. A. K., Khodorkovsky V, Shapiro L, Shames A. Eur. J. Org. Chem. 2001, 73.
    [15] Andreu R, Malfant I., Lacroix P. G, Cassoux P. Eur. J. Org. Chem. 2000, 737.
    [16] Liu S.-X., Dolder S., Pilkington M., Decurtins S. J. Org. Chem. 2002, 67, 3160.
    [17] (a) Campagna S., Serroni S., Puntoriero F., Loiseau F., De Cola L., Kleverlaan C. J., Becher J., Sorensen A. P., Hascoat P., Thorup N. Chem. Eur. J. 2002, 8, 4461; (b) Bouguessa S., Herv K., Golhen S., Ouahab L., Fabre J.-M. New J. Chem. 2003, 27, 560; (c) Liu S.-X., Dolder S., Rusanov E. B., Stoeckli-Evans H., Decurtins S., Acad C. R. Sci. Chimie. 2003, 6, 657.
    [18] (a) Iwahori F., Gohlen S., Ouahab L, Carlier R, Sutter J.-P. Inorg. Chem. 2001, 40, 6541; (b) Setifi F, Ouahab L, Gohlen S, YoshidaY, Saito G. Inorg. Chem. 2003, 42, 1791; (c) Ouahab L, Iwahori F, Gohlen S, CarlieR. r, Sutter J.-P. Synth. Met. 2003, 133, 505; (d) HervéK, Gal Y. L, Ouahab L, Golhen S, Cador O, Synth. Met. 2005, 153, 461.
    [19] O. Paz-Tal Levi, J. Y. Becker, A. Ellern, V. Khodorkovsky. Tetrahedron Letters, 2001, 42, 1571.
    [20] (a) Sheldrick, G. M. SHELXS-97, Program for structure solution, Universit?t of G?ttingen, Germany. 1999. (b) Sheldrick, G. M. SHELXL-97, Program for structure refinement, Universit?t of G?ttingen, Germany. 1997.
    [1] (a) Robertson, N.;Cronin,L.Coord. Chem. ReV. 2002, 227, 93-127.(b) Dithiolene Chemistry, Syntheses, Properties and Applications. In Progress in Inorgani Stiefel, E. I., Ed.; Wiley: New York, 2004; 52.
    [2] M. D. Ward, J. A. McCleverty, J. Chem. Soc., Dalton Trans. 2002, 275.
    [3] (a) R. Kimse, E. M?ller, C. Seitz, J. Reinhold, Z. Anorg. Allg. Chem. 1997, 623, 159. (b) W. E. Geiger, F. Barrie`re, R. J. LeSuer, S. Trupia, Inorg.Chem. 2001, 40, 2472. (c) K. Wung, Progr. Inorg. Chem. 2004, 52, 55.
    [4] P. Cassoux, Coord. Chem. Rev. 1999, 185, 213
    [5] (a) Winter, C. S; Oliver, S. N; Ruth, J. D; Hill, C. A. S; Underhill, A. E. J. Appl. Phys. 1992, 71, 512. (b) Winter, C. S; Oliver, S. N.; Manning, R. J.; Rush, J. D; Hill, C. A. S; Underhill, A. E. J. Mater. Chem. 1992, 2, 443.(c) Aloukos, P; Couris, S; Koutselas, J. B; Anyfantis, G. C; Papavassiliou,G. C. Chem. Phys. Lett. 2006, 428, 109.
    [6] Cassoux, P; Valade, L; Kobayashi, H; Kobayashi, A; Clark, R. A; Underhill, A. E. Coord. Chem. ReV. 1991, 110, 115.
    [7] (a) Mueller-Westerhoff,U.T; Vance, B.;Yoon, D. I. Tetrahedron 1991, 47, 909. (b) Bigoli, F.; Deplano, P; Devillanova, F.A; Lippolis, U; Lukes, P J.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Chem. Soc. Chem. Commun. 1995, 371. (c) Bigoli,F; Deplano,P;Devillanova,F.A; Frraro, J. R; Lippolis, U; Lukes,P.J; Mercuri, M L.; Pellinghelli, M.A; Trogu, E.F;Williams, J. M. InorgChem. 1997, 37, 1218 (d) Marshall, K L; Painter, G.; Lotito, K; Noto, A. G; Chang, P Mol. Cryst. Liq. Cryst. 2006, 454, 449.
    [8] Jeannin, O; Clerac, R.; Fourmigue, M. J. Am. Chem. Soc. 2006, 128, 14649.
    [9] (a) Lowe, N. D; Garner, C. D. J. Chem. Soc., Dalton Trans. 1993, 2197. (b) Nomura, M; Takayama, C; Kajitani, M. Inorg. Chem. 2003, 42, 6441.
    [10] Ofra P. T. L, James Y. B, Arkady E and Vladimir K, Tetrahedron. Lrtter. 2001, 42, 1571
    [11] Callum A.S.H, Adam C, Allan E U, Abdul M K M, Michael B.H, Karaulov A. I, Steven N, Oliver and Steven V. K, Chem. Soc, Dalton. Trans, 1995, 587
    [12] Lee H. J. and Noh D.Y, J. Mater. Chem. 2000, 10, 2167
    [13] Bondi, J.Phys.Chem, 1964, 68, 441