含氮、硫分子内电荷转移化合物的合成及性质研究
|
摘要
分子内电荷转移化合物是构筑光学材料的重要组成部分,已经逐渐成为一个非常活跃的研究领域。其中,分子内自身就含有电子供体与电子受体的D-A化合物因其容易发生光诱导分子内电荷转移而呈现出一些特有的光学性质,被广泛研究并应用于荧光发光材料、光电导材料以及非线性光学材料等领域,研究前景相当广阔。所以本论文以一种新型的含氮、硫共轭体系的分子内电荷转移化合物4',5'-二氮-9'-(4,5-二(硫烷基)-1,3-二硫-2-叶立德)-芴)为研究对象,对其进行研究,主要包括以下内容:
一、综述部分简要介绍了分子内电荷转移化合物的分类及应用前景,并介绍了含氮、硫共轭体系的分子内电荷转移化合物的研究进展以及质子化与金属配位对分子内电荷转移化合物性质的影响。
二、合成了化合物L~1与L~2,制备了L~1与CF_3SO_3H、HClO_4以及L~2与CF_3SO_3H的质子化合物,培养了L~2以及质子化合物的晶体,通过单晶衍射测定了晶体结构,并测试了它们的的红外光谱、荧光光谱、紫外-可见光谱以及核磁共振光谱,进一步探讨了质子化了的二氮芴部分与富硫的电子供体之间的分子内电荷转移效应。
三、制备了化合物L~1与Zn(NO_3)_2、ZnCl_2、Zn(PhCOO)_2、Zn(ClO_4)_2的配合物以及化合物L~2与Zn(ClO_4)_2的配合物,培养了配合物的晶体,通过单晶衍射测定了这些配合物的晶体结构,并测试了它们的光谱性质,探讨了配合物分子内电荷转移现象。
Intramolecular charge transfer (ICT) compounds are very important for optical materials and have been an active research area. Among them, D-A compounds, because of their unique molecular structure, have been extensively (?)nvestigated and widely studied in luminescent, photoconductive, nonlinear optical materials and so on. In this thesis, we pay attention to the study on a kind of new ICT compounds with N-S conjugated system. The major contents we researched were as follows:
In introduction, the classification and potential applications of ICT compounds are reviewed briefly. The research progresses of ICT compounds with N-S conjugated system are described, and the effects of protonation and metal coordination on ICT property were discussed.
In chapter 2, protonated compounds of L~1 with CF_3SO_3H,HClO_4 and L~2 with CF_3SO_3H were synthesized (L~1/L~2=4',5'-diaza-9'-(4,5-dimethylthio/diethylthio -1,3-dithiole-2-ylidene)fluorine).The crystal structures of L~2 and the protonated compounds were determined by single crystal X-ray diffraction. The IR,UV-vis, fluorescence and ~1HNMR spectra were also studied to further investigate the ICT effect between protonated diazafluorene and sulfur-rich moiety.
In chapter 3, five complexes of L~1 with Zn(NO_3)_2,Zn(PhCOO)_2,ZnCl_2, Zn(ClO_4)_2 and L~2 with Zn(ClO_4)_2 were prepared. The crystal structures of these complexes were determined by single crystal X-ray diffraction. The spectral properties were investigated and the ICT behaves of these complexes were also discussed.
一、综述部分简要介绍了分子内电荷转移化合物的分类及应用前景,并介绍了含氮、硫共轭体系的分子内电荷转移化合物的研究进展以及质子化与金属配位对分子内电荷转移化合物性质的影响。
二、合成了化合物L~1与L~2,制备了L~1与CF_3SO_3H、HClO_4以及L~2与CF_3SO_3H的质子化合物,培养了L~2以及质子化合物的晶体,通过单晶衍射测定了晶体结构,并测试了它们的的红外光谱、荧光光谱、紫外-可见光谱以及核磁共振光谱,进一步探讨了质子化了的二氮芴部分与富硫的电子供体之间的分子内电荷转移效应。
三、制备了化合物L~1与Zn(NO_3)_2、ZnCl_2、Zn(PhCOO)_2、Zn(ClO_4)_2的配合物以及化合物L~2与Zn(ClO_4)_2的配合物,培养了配合物的晶体,通过单晶衍射测定了这些配合物的晶体结构,并测试了它们的光谱性质,探讨了配合物分子内电荷转移现象。
Intramolecular charge transfer (ICT) compounds are very important for optical materials and have been an active research area. Among them, D-A compounds, because of their unique molecular structure, have been extensively (?)nvestigated and widely studied in luminescent, photoconductive, nonlinear optical materials and so on. In this thesis, we pay attention to the study on a kind of new ICT compounds with N-S conjugated system. The major contents we researched were as follows:
In introduction, the classification and potential applications of ICT compounds are reviewed briefly. The research progresses of ICT compounds with N-S conjugated system are described, and the effects of protonation and metal coordination on ICT property were discussed.
In chapter 2, protonated compounds of L~1 with CF_3SO_3H,HClO_4 and L~2 with CF_3SO_3H were synthesized (L~1/L~2=4',5'-diaza-9'-(4,5-dimethylthio/diethylthio -1,3-dithiole-2-ylidene)fluorine).The crystal structures of L~2 and the protonated compounds were determined by single crystal X-ray diffraction. The IR,UV-vis, fluorescence and ~1HNMR spectra were also studied to further investigate the ICT effect between protonated diazafluorene and sulfur-rich moiety.
In chapter 3, five complexes of L~1 with Zn(NO_3)_2,Zn(PhCOO)_2,ZnCl_2, Zn(ClO_4)_2 and L~2 with Zn(ClO_4)_2 were prepared. The crystal structures of these complexes were determined by single crystal X-ray diffraction. The spectral properties were investigated and the ICT behaves of these complexes were also discussed.
引文
[1] Mulliken, R.S.; J. Am. Chem.Soc, 1950, 72, 600.
[2] Mulliken, R.S.; J. Am. Chem. Soc, 1952,74,811.
[3] Mulliken, R.S.; J Phsy.Chem.,1952, 56, 801.
[4] Eva, M. Priego; Luis, Sanchez; M. Angeles, Herranz; Nazario, Martin;Rafael, Viruela; Enrique, Orti; Org. Biomol. Chem., 2007, 5, 1201.
[5] Take-aki, Koizumi; Kanako, Tsutsui; Koji, Tanaka; Eur. J. Org. Chem.,2003, 4528.
[6] Jongtae, Je; Oh-Kil, Kim; Macromol. Symp., 2007, 249-250, 44.
[7] Mikio, Yasutake; Toru, Koga; Youichi, Sakamoto; et al, J. Am. Chem. Soc,2002,124,10136.
[8] Evgeny, Tsiperman; James, Y. Becker; Vladimir, Khodorkovsky;Tetrahedron, Lett, 2007, 48, 4161.
[9] Rettig, W.; Gleiter, G.; JPhys Chem, 1985, 89(22), 4676.
[10] Fr(?)d(?)ric,Dumur; Nicolas, Gautier; Y(u|¨)cel, Sahin; Pi(?)trick, Hudhomme; et al,J.Org. Chem., 2004, 69, 2164.
[11] Jia,Chun-Yang; Xu, Yu; Xu, Wei; Zhu, Dao-Ben; Synth Met., 2003,137,979.
[12] Bonacic-Koutecky, V; Michl,J.;J.Am.Chem.Soc, 1985, 107, 1765.
[13] Burting, W.; Berib, S.; Egeerr, G.; et al, Syn. Met., 1997, 91, 325.
[14] Lu Z. Y, Zhu W. G, Xia M. G, Chin Chem Lett., 1999,10,679.
[15] 杨国强,吴世康,高等学校化学学报,1995,16(2),239.
[16] 赵波,卢文庆,吴芸,高等学校化学学报,2000,21(4),620.
[17] Krishnan, R.; Schlegel, H. B.; et al,Int J Quant Chem.,1978,14(5),545.
[18] 吴世康,化学世界,2005,17,16.
[19] Parg, R. P.; Kilburn, J. D.; Petty, M. C; Pearson, C; Ryan,T.G.;Synthesis,1994,613.
[20] Kukrek, A.; Wang, D.; Hou, Y.; Zong, R.; Thummel, R.;Inorg. Chem.,2006,45,10131.
[21]Chen,Ya;Liu,Wei;Liu,Bin;Zhou,Xin-Hui;Zou,Zhi-Gang;Zuo,Jing-Lin;You,Xiao-Zeng;Inorganica Chimica Acta,2009,362,143.
[22]Wu,Jin-cai;Liu,Shi-Xia;Antonia,Neels;Franck,Le.Derf;et al,Tetrahedron,2007,63,11282.
[23]Joshi,H.S.;Jamshidi,R.;Tor,Y.;Angew.Chem.,Int.Ed,1999,38,2722.
[24]Greiner,G.,Maier,I.;J.Chem.Soc,Perkin Trans.,2002,2,1005.
[25]Higgins,B.;DeGraff,B.A.;Demas,J.N.;Inorg.Chem.,2005,44,6662.
[26]Wong,K.M.C;Tang,W.S.;Lu,X.X.;Zhu,N.Y.;Yam,V.W.W.;Inorg.Chem.,2005,44,1492.
[27]Jangwon,Seo;Sehoon,Kim;Soo,Young Park;J.Am.Chem.Soc,2004,126,11154.
[28](a)Kim,S.K;Yoon,J.;Chem.Commun.2002,770.(b)Gunnlaugsson,T.;Davis,A.P.;Hussey,G.M.;Tierney,J.;Glynn,M.;Org.Biomol.Chem.,2004,2,1856.(c)Gunnlaugsson,T.;Davis,A.P.;O'Brien,J.E.;Glynn,M.;Org.Lett,2002,4,2449.(d)Gunnlaugsson,T.;Davis,A.P.;Glynn,M.;Chem.Commun.,2001,2556.(e)Nishizawa,S.;Kaneda,H.;Uchida,T.;Teramae,N.;J.Chem.Soc,Perkin Trans.1998,2325.(f)Nishizawa,S.;Kato,Y.;Teramae,N.;J.Am.Chem.Soc,1999,121,9463-9464.(g)Vance,D.H.;Czarnik,A.W.;J.Am.Chem.Soc.1994,116,9397.
[29](a)Kovalchuk,A.;Bricks,J.L.;Reck,G.;Rurack,K.;Schulz,B.;Szumna,A.;Weibhoff,H.;Chem.Commun.,2004,1946.(b)Wu,F.-Y.;Jiang,Y.-B.;Chem.Phys.Lett,2002,555,438.
[30](a)Zhang,X.;Guo,L.;Wu,F.-Y.;Jiang,Y.-B.;Org.Lett,2003,5,2667.(b)Choi,K.;Hamilton,A.D.;Angew.Chem.,Int.Ed:2001,40,3912.
[31]Robson,Valentim,Pereira;Ana,Paula,Garcia,Ferreira;Marcelo,Henrique,Gehlen;J.Phys.Chem.A.,2005,109,5978.
[32]Zhu,Qin-Yu;Liu,Yu;Lu,Wen;Zhang,Yong;Bian,Guo-Qing;Niu,Gai-Yan;Dai,Jie;Inorg.Chem.,2007,46,10065.
[33]Pablo,R.;Sainz-Rozas;Jose,Ramon Isasi;Miguel,Sanchez;Gloria,Tardajos;Gustavo,Gonzalez-Gaitano;J.Phys.Chem.A.,2004,108,392.
[34] Andrea, Listorti; Alessandra, Degli Esposti; Ravuri, S. K. Kishore;Venkateshwarlu, Kalsani; Michael, Schmittel; Nicola, Armaroli; J. Phys. Chem. A,2007, 111,7707.
[35] Wu,Jin-cai; Dupont,Nathalie; Liu, Shi-Xia; Neels,Antonia; Hauser,Andreas; Decurtins, Silvio; Chem. Asian J., 2009, 4, 392.
[36] Xu, Zhao-chao; Xiao Yi, Qian Xu-hong; Cui, Jing-nan; Cui, Da-wei; Org.Lett., 2005, 7. 889.
[37] Beer, P. D.;Acc.Chem. Res., 1998,31,71.
[38] Valeur, B.; Leray, I.; Coord. Chem. ReV., 2000, 205, 3.
[39] Henary, M. M.;Fahrni, C. J.; J. Phys. Chem. A. 2002,106,5210.
[40] Henary, M. M.; Wu, Y.; Fahrni, C. J.; Chem.-Eur.J., 2004,10,3015.
[41] Zhang, Lu; Zhu, Lei; J. Org. Chem., 2008, 73, 8321.
[42] Thorfinnur, Gunnlaugsson; Joseph, P. Leonard; Niamh,S. Murray; Org.Lett., 2004, 6, 1557.
[43] (a) de, Silva; A. P.; Nimal,Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A.J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E.; Chem. ReV., 1997, 97, 1515.(b)Valeur, B.; Leray, I.; Coord. Chem. ReV., 2000, 205, 3. (c) Prodi, L.; Bolletta, F.;Montalti, M.; Zaccheroni, N.; Coor. Chem. ReV., 2000, 205, 59. (d) Rurack, K.;Spectrochim.Acta A 2001, 57, 2161.
[44] Peng, Xiao-jun; Du, Jian-jun; Fan, Jiang-li;Wang, Jing-yun; Wu, Yun-kou;Zhao, Jian-zhang; Sun, Shi-guo; Xu, Tao; J. Am. Chem. Soc, 2007,129,1500.
[45] Wang, Jiao-bing; Qian,Xu-hong; Cui, Jing-nan; J. Org. Chem. 2006, 71,4308.
[46] Evgeny, Tsiperman; James, Y. Becker; Vladimir, Khodorkovsky;Tetrahedron Lett., 2007, 48, 4161.
[47] Mikio, Yasutake; Toru, Koga; Youichi, Sakamoto; et al,J. Am. Chem. Soc,2002,124,10136.
[48] Nicolas, Gautier; Nuria, Gallego-Planas; et al, J. Org. Chem., 2004, 69,2164.
[49] Dmaodarna, B.; Krishnpaillai, S.; J. Mater. Chem., 1999, 9, 1425.
[1] (a) Belser, P.; Cola, L. D.; Haiti,F.;Adamo,V.; Bozic, B.; Chriqui, Y.; Lyer,V. M; Jukes, R. T. E; Kiihni, J.; Querol, M; Roma, S.; Salluce, N. Adv. Funct.Mate.2006, 16, 195-208. (b) Wong, K.-T.; Chen, H.-E; Fang, E-C. Org. Lett. 2006, 8,3501-3504. (c) Su, H.-C; Chen, H.-E; Wu, C.-C; Wong, K.-T. Chemistry Asian J.an early view paper.
[2] (a) Sans, M. Q.; Belser, P. Coord. Chem.Rev. 2002, 229, 59-66. (b) Wong,W.-Y. Coord. Chem. Rev. 2005, 249, 971-997.
[3] (a) Warrener, R. N.; Ferreira, A. B. B.; Schultz, A. C; Butler, D. N., Keene,F. R., Kelso, L. S. Angew. Chem. Int. Ed. 1996, 55, 2485-2487. (b) Kraft, B. J.,Eppley, H. J., Huffman, J. C; Zaleski, J. M. J. Am. Chem. Soc.2002,124, 272-280.
[4] Joshi, H. S.; Jamshidi, R.; Tor, Y.; Angew. Chem., Int. Ed, 1999, 38, 2722.
[5] Greiner, G.; Maier, I.; J. Chem. Soc, Perkin Trans., 2002, 2, 1005.
[6] Higgins, B.; DeGraff, B. A.; Demas, J. N.; Inorg.Chem., 2005, 44, 6662.
[7] Wong, K. M. C; Tang, W. S.; Lu, X. X.; Zhu, N. Y.; Yam, V. W. W.; Inorg.Chem., 2005, 44,1492.
[8] Pan, J.-E; Chen, Z.-K.; Chua, S.-J.; Huang, W. J. Phys. Chem. A. 2001,105,8775-8781.
[9] (a)Armaroli, N.;De Cola, L.; Balzani,V.; Sauvage, J. P.;Dietrich-Buchecker,C.O.;Kern, J. M. J. Chem. Soc, Faraday Trans. 1992, 88, 553-556. (b)Dietrich-Buchecker, C.O.;Sauvage, J. P.; Armaroli, N.; Ceroni,P.; Balzani, V. New J.Chem. 1996, 20, 801. (c) Armaroli, N.; Ceroni, P.; Balzani, V.; Kern, J. M.; Sauvage,J. P.;Weidmann, J. L. J. Chem. Soc, Faraday Trans. 1997, 93, 4145-4150.(d)Armaroli; N. Photochem.Photobiol.Sci.2003, 2, 73-87. (e) Listorti, A.; Degli Esposti, A.; Kishore, R. S. K.; Kalsani, V.; Schmittel, M.; Armaroli, N. J. Phys. Chem.A 2007, 111,7707-7718.
[10] Sammes, P. G.; Yahioglu, G.; Chem. Soc Rev. 1994, 327.
[11]Pena-Cabrera,E.;Norrby,P.0.;Sjogren,M.;Vitagliano,A.;Felice,V.;De,Oslob J.,Ishii S.,O'Neill D.,Akermark B.,Helquist P.,J.Am.Chem.Soc,1996,118,4299.
[12]Klein,A.;Kaim,W.;Waldhor,E.;Hausen,H.D.;J.Chem.Soc,Perkin Trans.,1995,2,2121.
[13]Ernst,S.;Vogler,C;Klein,A.;Kaim,W.;Zalis,S.;Inorg.Chem.1996,35,1295.
[14]Henderson,L.J.;Frank,J.;Fronczek,R.;William,R.;J.Am.Chem.Soc.1984,106,5876.
[15]Svenstrup,N.;Rasmussen,K.M.;Hansen,T.K.;Becher,J.;Synthesis,1994,809.
[16]Svenstrup,N.;Becher,J.;Synthesis,1995,215.
[17]Sako,K.;Kusakabe,M.;Tatemitsu,H.;Mol.Cryst.Liq.Cryst,1996,255,101.
[18]Kulkarni,P.;Padhye,S.;Sinn,E.;Inorg.Chim.Acta,2001,321,193.
[1] Lipscomb, W. N; Strater, N.; Recent advances in zinc enzymology[J]. Chem.Rev. 1996, 96(7), 2375-2434.
[2] 席振峰,姚光庆,项斯芬,等译.生物无机化学原理[M].北京:北京大学出版社,2000,1.
[3] Zhang, Jing; Lin, Wenbin; Chen; Zhen-Feng; Xiong; Ren-Gen; Abrahams,Brendan, F.; Fun, Hoong-Kun; J. Chem. Soc, Dalton Trans., 2001,1806-1808.
[4] Lin, Wenbin; Evans, Owen, R.; Xiong, Rengen; Wang, Zhiyong; J. Am.Chem. Soc, 1998 ,120 :13272 -13273.
[5] Ayala, N. P., Flynn, C. M. Jr.; Sacksteder, L.; Demas, J. N.; DeGraff,B.A.; J.Am.Chem. Soc. 1990,112,3837.
[6] Kam-Wing, L. Kenneth; Wai-Ki, H.; Chun-Ming, N. Dominic; Kung-Kai, C;Inorg. Chem. 2002, 41,40.
[7] Sammes, P. G; Yahioglu, G; Chem. Soc. Rev. 1994, 327.
[8] Pe(?)a-Cabrera, E.; Norrby, P.O.; Jogren, M. S; Vitagliano, A.; Felice, V. De;Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P.; J. Am. Chem. Soc. 1996,118, 4299.
[9] Klein, A.; Kaim,W; Waldhor, E.; Hausen, H. D.; J. Chem. Soc, Perkin Trans.1995,2,2121.
[10] Ernst, S.; Vogler, C; Klein, A.; Kaim, W; Zalis,S.; Inorg.Chem.1996, 55,1295.
[11] Dmitry, N.; Kozhevnikov;Olga,V.; Shabunina; Dmitry, S.; Kopchuk;Pavel, A.; Slepukhina; Valery, N.; Kozhevnikov;Tetrahedron Lett 2006, 47, 7025.
[12] Liu, Xiao-ming; Mu, Xiao-yue; Xia, Hong; Ye, Ling; Gao, Wei; Wang,Hao-yu; Mu, Ying; Eur. J. Inorg. Chem., 2006, 4317.
[13] Sanjib, Das; Parimal, K.; Bharadwaj; Cryst. Growth Des.,2006, 6,187.
[14] Ye, Bao-Hui; Xue, Feng; Xue, Gen-Qiang; Jia, Liang-Nian; Thomas, C.W.;Mak, Polyhedron, 1999, 18, 1785.
[15] Kwong, Hoi-Lun; Lau, Kwok-Mei; Lee, Wing-Sze; Wong, Wing-Tak; New J.Chem.,1999, 23, 629.
[16] Charles, J.; Simmons; Brian, J.; Hathaway; Kitti, Amornjarusiri; Bernard,D.; Santarsiero; Abraham, Clearfield; J. Am. Chem. Soc, 1987,109,1947.
[17] Sanjib, Das; Parimal, K. Bharadwaj; Inorg. Chem., 2006, 45, 5257.
[18] Rice, Craig R.; Onions, Stuart; Vidal,Natalia; Wallis, John, D.; Senna,Maria-Cristina; Pilkington, Melanie; Helen, Stoeckli-Evans; Eur. J. Inorg. Chem.,2002,1985.
[19] Janiak,Christoph; Deblon, Stephan; Wu, He-Ping; Kolm,Mario,J.,Kl(u|¨)fers, Peter; Piotrowski, Holger; Mayer, Peter; Eur. J. Inorg,Chem.,1999,1507.
[20] Xue,Ming; Zhu, Guang-shan; Hong, Ding; Wu, Lei; Zhao, Xiao-jun; Jin,Zhao; Qiu, Shi-lun;Cryst. Growth Des., 2009, 9,1481.
[21] Henderson, L. J.; Frank, J.; Fronczek, R.; William, R.; J. Am. Chem. Soc.1984,106,5876.
[22] Svenstrup, N.; Rasmussen, K. M.; Hansen, T. K.; Becher, J.; Synthesis,1994, 809.
[23] Svenstrup, N.; Becher, J.; Synthesis, 1995, 215.
[24] Sako, K.; Kusakabe, M.; Tatemitsu, H.; Mol.Cryst. Liq. Cryst,1996,255,101.
[25] Chen, Xu; Hong-Yan, Mao; Hong-Yun, Zhang; Hong-Lei, Liu; Qing-An,Wu; Hong-Wei, Hou; Yu, Zhu; J. Inorg. Chem., 2004, 20, 539-542.
[26] Jing-Hua, Xu; Jian-Ming, Gu; J. Inorg. Chem., 1998,14,237-240.
[27] Masood, A. Khan, Dennis, G. Tuck; Acta Cryst. 1984, C40, 60-62.
[2] Mulliken, R.S.; J. Am. Chem. Soc, 1952,74,811.
[3] Mulliken, R.S.; J Phsy.Chem.,1952, 56, 801.
[4] Eva, M. Priego; Luis, Sanchez; M. Angeles, Herranz; Nazario, Martin;Rafael, Viruela; Enrique, Orti; Org. Biomol. Chem., 2007, 5, 1201.
[5] Take-aki, Koizumi; Kanako, Tsutsui; Koji, Tanaka; Eur. J. Org. Chem.,2003, 4528.
[6] Jongtae, Je; Oh-Kil, Kim; Macromol. Symp., 2007, 249-250, 44.
[7] Mikio, Yasutake; Toru, Koga; Youichi, Sakamoto; et al, J. Am. Chem. Soc,2002,124,10136.
[8] Evgeny, Tsiperman; James, Y. Becker; Vladimir, Khodorkovsky;Tetrahedron, Lett, 2007, 48, 4161.
[9] Rettig, W.; Gleiter, G.; JPhys Chem, 1985, 89(22), 4676.
[10] Fr(?)d(?)ric,Dumur; Nicolas, Gautier; Y(u|¨)cel, Sahin; Pi(?)trick, Hudhomme; et al,J.Org. Chem., 2004, 69, 2164.
[11] Jia,Chun-Yang; Xu, Yu; Xu, Wei; Zhu, Dao-Ben; Synth Met., 2003,137,979.
[12] Bonacic-Koutecky, V; Michl,J.;J.Am.Chem.Soc, 1985, 107, 1765.
[13] Burting, W.; Berib, S.; Egeerr, G.; et al, Syn. Met., 1997, 91, 325.
[14] Lu Z. Y, Zhu W. G, Xia M. G, Chin Chem Lett., 1999,10,679.
[15] 杨国强,吴世康,高等学校化学学报,1995,16(2),239.
[16] 赵波,卢文庆,吴芸,高等学校化学学报,2000,21(4),620.
[17] Krishnan, R.; Schlegel, H. B.; et al,Int J Quant Chem.,1978,14(5),545.
[18] 吴世康,化学世界,2005,17,16.
[19] Parg, R. P.; Kilburn, J. D.; Petty, M. C; Pearson, C; Ryan,T.G.;Synthesis,1994,613.
[20] Kukrek, A.; Wang, D.; Hou, Y.; Zong, R.; Thummel, R.;Inorg. Chem.,2006,45,10131.
[21]Chen,Ya;Liu,Wei;Liu,Bin;Zhou,Xin-Hui;Zou,Zhi-Gang;Zuo,Jing-Lin;You,Xiao-Zeng;Inorganica Chimica Acta,2009,362,143.
[22]Wu,Jin-cai;Liu,Shi-Xia;Antonia,Neels;Franck,Le.Derf;et al,Tetrahedron,2007,63,11282.
[23]Joshi,H.S.;Jamshidi,R.;Tor,Y.;Angew.Chem.,Int.Ed,1999,38,2722.
[24]Greiner,G.,Maier,I.;J.Chem.Soc,Perkin Trans.,2002,2,1005.
[25]Higgins,B.;DeGraff,B.A.;Demas,J.N.;Inorg.Chem.,2005,44,6662.
[26]Wong,K.M.C;Tang,W.S.;Lu,X.X.;Zhu,N.Y.;Yam,V.W.W.;Inorg.Chem.,2005,44,1492.
[27]Jangwon,Seo;Sehoon,Kim;Soo,Young Park;J.Am.Chem.Soc,2004,126,11154.
[28](a)Kim,S.K;Yoon,J.;Chem.Commun.2002,770.(b)Gunnlaugsson,T.;Davis,A.P.;Hussey,G.M.;Tierney,J.;Glynn,M.;Org.Biomol.Chem.,2004,2,1856.(c)Gunnlaugsson,T.;Davis,A.P.;O'Brien,J.E.;Glynn,M.;Org.Lett,2002,4,2449.(d)Gunnlaugsson,T.;Davis,A.P.;Glynn,M.;Chem.Commun.,2001,2556.(e)Nishizawa,S.;Kaneda,H.;Uchida,T.;Teramae,N.;J.Chem.Soc,Perkin Trans.1998,2325.(f)Nishizawa,S.;Kato,Y.;Teramae,N.;J.Am.Chem.Soc,1999,121,9463-9464.(g)Vance,D.H.;Czarnik,A.W.;J.Am.Chem.Soc.1994,116,9397.
[29](a)Kovalchuk,A.;Bricks,J.L.;Reck,G.;Rurack,K.;Schulz,B.;Szumna,A.;Weibhoff,H.;Chem.Commun.,2004,1946.(b)Wu,F.-Y.;Jiang,Y.-B.;Chem.Phys.Lett,2002,555,438.
[30](a)Zhang,X.;Guo,L.;Wu,F.-Y.;Jiang,Y.-B.;Org.Lett,2003,5,2667.(b)Choi,K.;Hamilton,A.D.;Angew.Chem.,Int.Ed:2001,40,3912.
[31]Robson,Valentim,Pereira;Ana,Paula,Garcia,Ferreira;Marcelo,Henrique,Gehlen;J.Phys.Chem.A.,2005,109,5978.
[32]Zhu,Qin-Yu;Liu,Yu;Lu,Wen;Zhang,Yong;Bian,Guo-Qing;Niu,Gai-Yan;Dai,Jie;Inorg.Chem.,2007,46,10065.
[33]Pablo,R.;Sainz-Rozas;Jose,Ramon Isasi;Miguel,Sanchez;Gloria,Tardajos;Gustavo,Gonzalez-Gaitano;J.Phys.Chem.A.,2004,108,392.
[34] Andrea, Listorti; Alessandra, Degli Esposti; Ravuri, S. K. Kishore;Venkateshwarlu, Kalsani; Michael, Schmittel; Nicola, Armaroli; J. Phys. Chem. A,2007, 111,7707.
[35] Wu,Jin-cai; Dupont,Nathalie; Liu, Shi-Xia; Neels,Antonia; Hauser,Andreas; Decurtins, Silvio; Chem. Asian J., 2009, 4, 392.
[36] Xu, Zhao-chao; Xiao Yi, Qian Xu-hong; Cui, Jing-nan; Cui, Da-wei; Org.Lett., 2005, 7. 889.
[37] Beer, P. D.;Acc.Chem. Res., 1998,31,71.
[38] Valeur, B.; Leray, I.; Coord. Chem. ReV., 2000, 205, 3.
[39] Henary, M. M.;Fahrni, C. J.; J. Phys. Chem. A. 2002,106,5210.
[40] Henary, M. M.; Wu, Y.; Fahrni, C. J.; Chem.-Eur.J., 2004,10,3015.
[41] Zhang, Lu; Zhu, Lei; J. Org. Chem., 2008, 73, 8321.
[42] Thorfinnur, Gunnlaugsson; Joseph, P. Leonard; Niamh,S. Murray; Org.Lett., 2004, 6, 1557.
[43] (a) de, Silva; A. P.; Nimal,Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A.J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E.; Chem. ReV., 1997, 97, 1515.(b)Valeur, B.; Leray, I.; Coord. Chem. ReV., 2000, 205, 3. (c) Prodi, L.; Bolletta, F.;Montalti, M.; Zaccheroni, N.; Coor. Chem. ReV., 2000, 205, 59. (d) Rurack, K.;Spectrochim.Acta A 2001, 57, 2161.
[44] Peng, Xiao-jun; Du, Jian-jun; Fan, Jiang-li;Wang, Jing-yun; Wu, Yun-kou;Zhao, Jian-zhang; Sun, Shi-guo; Xu, Tao; J. Am. Chem. Soc, 2007,129,1500.
[45] Wang, Jiao-bing; Qian,Xu-hong; Cui, Jing-nan; J. Org. Chem. 2006, 71,4308.
[46] Evgeny, Tsiperman; James, Y. Becker; Vladimir, Khodorkovsky;Tetrahedron Lett., 2007, 48, 4161.
[47] Mikio, Yasutake; Toru, Koga; Youichi, Sakamoto; et al,J. Am. Chem. Soc,2002,124,10136.
[48] Nicolas, Gautier; Nuria, Gallego-Planas; et al, J. Org. Chem., 2004, 69,2164.
[49] Dmaodarna, B.; Krishnpaillai, S.; J. Mater. Chem., 1999, 9, 1425.
[1] (a) Belser, P.; Cola, L. D.; Haiti,F.;Adamo,V.; Bozic, B.; Chriqui, Y.; Lyer,V. M; Jukes, R. T. E; Kiihni, J.; Querol, M; Roma, S.; Salluce, N. Adv. Funct.Mate.2006, 16, 195-208. (b) Wong, K.-T.; Chen, H.-E; Fang, E-C. Org. Lett. 2006, 8,3501-3504. (c) Su, H.-C; Chen, H.-E; Wu, C.-C; Wong, K.-T. Chemistry Asian J.an early view paper.
[2] (a) Sans, M. Q.; Belser, P. Coord. Chem.Rev. 2002, 229, 59-66. (b) Wong,W.-Y. Coord. Chem. Rev. 2005, 249, 971-997.
[3] (a) Warrener, R. N.; Ferreira, A. B. B.; Schultz, A. C; Butler, D. N., Keene,F. R., Kelso, L. S. Angew. Chem. Int. Ed. 1996, 55, 2485-2487. (b) Kraft, B. J.,Eppley, H. J., Huffman, J. C; Zaleski, J. M. J. Am. Chem. Soc.2002,124, 272-280.
[4] Joshi, H. S.; Jamshidi, R.; Tor, Y.; Angew. Chem., Int. Ed, 1999, 38, 2722.
[5] Greiner, G.; Maier, I.; J. Chem. Soc, Perkin Trans., 2002, 2, 1005.
[6] Higgins, B.; DeGraff, B. A.; Demas, J. N.; Inorg.Chem., 2005, 44, 6662.
[7] Wong, K. M. C; Tang, W. S.; Lu, X. X.; Zhu, N. Y.; Yam, V. W. W.; Inorg.Chem., 2005, 44,1492.
[8] Pan, J.-E; Chen, Z.-K.; Chua, S.-J.; Huang, W. J. Phys. Chem. A. 2001,105,8775-8781.
[9] (a)Armaroli, N.;De Cola, L.; Balzani,V.; Sauvage, J. P.;Dietrich-Buchecker,C.O.;Kern, J. M. J. Chem. Soc, Faraday Trans. 1992, 88, 553-556. (b)Dietrich-Buchecker, C.O.;Sauvage, J. P.; Armaroli, N.; Ceroni,P.; Balzani, V. New J.Chem. 1996, 20, 801. (c) Armaroli, N.; Ceroni, P.; Balzani, V.; Kern, J. M.; Sauvage,J. P.;Weidmann, J. L. J. Chem. Soc, Faraday Trans. 1997, 93, 4145-4150.(d)Armaroli; N. Photochem.Photobiol.Sci.2003, 2, 73-87. (e) Listorti, A.; Degli Esposti, A.; Kishore, R. S. K.; Kalsani, V.; Schmittel, M.; Armaroli, N. J. Phys. Chem.A 2007, 111,7707-7718.
[10] Sammes, P. G.; Yahioglu, G.; Chem. Soc Rev. 1994, 327.
[11]Pena-Cabrera,E.;Norrby,P.0.;Sjogren,M.;Vitagliano,A.;Felice,V.;De,Oslob J.,Ishii S.,O'Neill D.,Akermark B.,Helquist P.,J.Am.Chem.Soc,1996,118,4299.
[12]Klein,A.;Kaim,W.;Waldhor,E.;Hausen,H.D.;J.Chem.Soc,Perkin Trans.,1995,2,2121.
[13]Ernst,S.;Vogler,C;Klein,A.;Kaim,W.;Zalis,S.;Inorg.Chem.1996,35,1295.
[14]Henderson,L.J.;Frank,J.;Fronczek,R.;William,R.;J.Am.Chem.Soc.1984,106,5876.
[15]Svenstrup,N.;Rasmussen,K.M.;Hansen,T.K.;Becher,J.;Synthesis,1994,809.
[16]Svenstrup,N.;Becher,J.;Synthesis,1995,215.
[17]Sako,K.;Kusakabe,M.;Tatemitsu,H.;Mol.Cryst.Liq.Cryst,1996,255,101.
[18]Kulkarni,P.;Padhye,S.;Sinn,E.;Inorg.Chim.Acta,2001,321,193.
[1] Lipscomb, W. N; Strater, N.; Recent advances in zinc enzymology[J]. Chem.Rev. 1996, 96(7), 2375-2434.
[2] 席振峰,姚光庆,项斯芬,等译.生物无机化学原理[M].北京:北京大学出版社,2000,1.
[3] Zhang, Jing; Lin, Wenbin; Chen; Zhen-Feng; Xiong; Ren-Gen; Abrahams,Brendan, F.; Fun, Hoong-Kun; J. Chem. Soc, Dalton Trans., 2001,1806-1808.
[4] Lin, Wenbin; Evans, Owen, R.; Xiong, Rengen; Wang, Zhiyong; J. Am.Chem. Soc, 1998 ,120 :13272 -13273.
[5] Ayala, N. P., Flynn, C. M. Jr.; Sacksteder, L.; Demas, J. N.; DeGraff,B.A.; J.Am.Chem. Soc. 1990,112,3837.
[6] Kam-Wing, L. Kenneth; Wai-Ki, H.; Chun-Ming, N. Dominic; Kung-Kai, C;Inorg. Chem. 2002, 41,40.
[7] Sammes, P. G; Yahioglu, G; Chem. Soc. Rev. 1994, 327.
[8] Pe(?)a-Cabrera, E.; Norrby, P.O.; Jogren, M. S; Vitagliano, A.; Felice, V. De;Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P.; J. Am. Chem. Soc. 1996,118, 4299.
[9] Klein, A.; Kaim,W; Waldhor, E.; Hausen, H. D.; J. Chem. Soc, Perkin Trans.1995,2,2121.
[10] Ernst, S.; Vogler, C; Klein, A.; Kaim, W; Zalis,S.; Inorg.Chem.1996, 55,1295.
[11] Dmitry, N.; Kozhevnikov;Olga,V.; Shabunina; Dmitry, S.; Kopchuk;Pavel, A.; Slepukhina; Valery, N.; Kozhevnikov;Tetrahedron Lett 2006, 47, 7025.
[12] Liu, Xiao-ming; Mu, Xiao-yue; Xia, Hong; Ye, Ling; Gao, Wei; Wang,Hao-yu; Mu, Ying; Eur. J. Inorg. Chem., 2006, 4317.
[13] Sanjib, Das; Parimal, K.; Bharadwaj; Cryst. Growth Des.,2006, 6,187.
[14] Ye, Bao-Hui; Xue, Feng; Xue, Gen-Qiang; Jia, Liang-Nian; Thomas, C.W.;Mak, Polyhedron, 1999, 18, 1785.
[15] Kwong, Hoi-Lun; Lau, Kwok-Mei; Lee, Wing-Sze; Wong, Wing-Tak; New J.Chem.,1999, 23, 629.
[16] Charles, J.; Simmons; Brian, J.; Hathaway; Kitti, Amornjarusiri; Bernard,D.; Santarsiero; Abraham, Clearfield; J. Am. Chem. Soc, 1987,109,1947.
[17] Sanjib, Das; Parimal, K. Bharadwaj; Inorg. Chem., 2006, 45, 5257.
[18] Rice, Craig R.; Onions, Stuart; Vidal,Natalia; Wallis, John, D.; Senna,Maria-Cristina; Pilkington, Melanie; Helen, Stoeckli-Evans; Eur. J. Inorg. Chem.,2002,1985.
[19] Janiak,Christoph; Deblon, Stephan; Wu, He-Ping; Kolm,Mario,J.,Kl(u|¨)fers, Peter; Piotrowski, Holger; Mayer, Peter; Eur. J. Inorg,Chem.,1999,1507.
[20] Xue,Ming; Zhu, Guang-shan; Hong, Ding; Wu, Lei; Zhao, Xiao-jun; Jin,Zhao; Qiu, Shi-lun;Cryst. Growth Des., 2009, 9,1481.
[21] Henderson, L. J.; Frank, J.; Fronczek, R.; William, R.; J. Am. Chem. Soc.1984,106,5876.
[22] Svenstrup, N.; Rasmussen, K. M.; Hansen, T. K.; Becher, J.; Synthesis,1994, 809.
[23] Svenstrup, N.; Becher, J.; Synthesis, 1995, 215.
[24] Sako, K.; Kusakabe, M.; Tatemitsu, H.; Mol.Cryst. Liq. Cryst,1996,255,101.
[25] Chen, Xu; Hong-Yan, Mao; Hong-Yun, Zhang; Hong-Lei, Liu; Qing-An,Wu; Hong-Wei, Hou; Yu, Zhu; J. Inorg. Chem., 2004, 20, 539-542.
[26] Jing-Hua, Xu; Jian-Ming, Gu; J. Inorg. Chem., 1998,14,237-240.
[27] Masood, A. Khan, Dennis, G. Tuck; Acta Cryst. 1984, C40, 60-62.