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Progress in Chemistry 2009, Vol. 21 Issue (01): 164-173 Previous Articles   Next Articles

• Review •

Research Progress of Cucurbituril

Yang Hui;Tan Yebang**;Huang Xiaoling;Wang Yuexia   

  1. (School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China)
  • Received: Revised: Online: Published:
  • Contact: Tan Yebang E-mail:ybtan@sdu.edu.cn
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In recent years, cucurbituril(CB[n]) and its derivatives have attracted considerable attentions because of their special structures and properties. In this paper, the new development of cucurbituril is summarized, including the design and synthesize of cucurbituril and their derivatives, forming the main-chain (pseudo) polyrotaxanes and side-chian (pseudo) polyrotaxane with the polyelectrolyte, and forming (pseudo) rotaxane with other organic guest molecules. Applications of cucurbituril are also reviewed including vesicles,2D polymers,stationary phases in chromatography, organism and drug release.

Contents
1 Synthesis
1.1 Synthesis of CB[n] analogues and congeners
1.2 Functionalization of CB[n]
1.2.1 Fully substituted CB[n] using substituted glycoluril
1.2.2 Partially substituted CB[n] using substituted glycoluril
1.2.3 Direct substituented CB[n]
2 Structure and characteristic of CB[n]
3 The formation of (pseudo)rotaxane by assembly of CB[n] with other molecules
3.1 Synthesis of polyrotaxanes using CB[n] as the catalyst by organic polymerization reaction
3.2 Side-chain polyrotaxane containing CB[n]
3.3 Interaction between CB[n] and other organic guest molecules
4 Applications
4.1 Vesicles
4.2 2D polymers
4.3 Application of CB[n] in chromatography
4.4 The development of CB[n] in organism and controlled drug delivery
5 Conclusions and outlook

Key words: cucurbituril, self-assembly, rotaxane, organic guest molecules

CLC Number: 

[ 1 ] 　刘育(Liu Y) , 尤长城(You C C) , 张衡益(Zhang H Y) . 超分子化学: 合成受体的分子识别与组装( Supramolecular Chemistry: Molecular Recognition and Assembly of Synthetic Receptors) . 天津: 南开大学出版社(Tianjin : Nankai University Press) , 2001. 385
[ 2 ] 　韩宝(Hang B H) , 刘育(Liu Y) . 有机化学(Chin. J . Org.Chem. ) , 2002 , 23 (2) : 139 —149
[ 3 ] 　Kim K. Chem. Soc. Rev. , 2002 , 31 (2) : 96 —107
[ 4 ] 　Lee J W, Samal S , Selvapalam N , et al . Acc. Chem. Res. , 2003 ,36 : 621 —630
[ 5 ] 　侯昭升(Hou Z S) , 谭业邦(Tan Y B) , 黄玉玲(Huang YL)等. 高分子通报(Chinese Polymer Bulletin) , 2005 , 3 : 47 —54
[ 6 ] 　Kim K, Selvapalam N , Oh D H. J . Inclusion Phenom. Macrocyclic.Chem. , 2004 , 50 : 31 —36
[ 7 ] 　Lagona J , Mukhopadhyay P , Chakrabarti S , et al . Angew. Chem.Int . Ed. , 2005 , 44 (31) : 4844 —4870
[ 8 ] 　Huang F H , Gibson H W. Prog. Polym. Sci . , 2005 , 30 : 982 —1018
[ 9 ] 　刘思敏(Liu S M) , 吴成泰(Wu C T) . 化学进展( Progress in Chemistry) , 2005 , 17 (1) : 143 —150
[10 ] 　张锐(Zhang R) , 薛红(Xue H) . 化工技术与开发(Technology&Development of Chemical Industry) , 2005 , 34 (1) : 24 —26
[11 ] 　江慧(Jiang H) , 韩莹( Han Y) , 李梅(Li M) . 化学研究(Chemical Research) , 2005 , 16 (1) : 99 —104
[12 ] 　霍方俊(Huo F J ) , 阴彩霞(Yin C X) , 杨频(Yang P) . 化学研究(Chemical Research) , 2006 , 17 (3) : 103 —107
[13 ] 　Behrend R , Meyer E , Rusche F. Justus Liebigs Ann. Chem. ,1905 , 339 : 1 —37
[14 ] 　Freeman W A , Mock W L , Shih N Y. J . Am. Chem. Soc. , 1981 ,103 (24) : 7367 —7368
[15 ] 　Buschmann HJ , Fink H , Schollmeyer E. DE 19603377 , 1997.
[16 ] 　Kim J , Jung I S , Kim S Y, et al . J . Am. Chem. Soc. , 2000 , 122 (3) : 540 —541
[17 ] 　毕强(Bi Q) , 胡英鹏(Hu Y P) , 杨琴(Yang Q) 等. 有机化学(Chin. J . Org. Chem. ) , 2007 , 27 (7) : 880 —884
[18 ] 　Jansen K, Buschmann H J , Wego A , et al . J . Incl . Phenom.Macrocyclic Chem. , 2001 , 39 : 357 —363
[19 ] 　Day A I , Blanch R J , Arnold A P , et al . Angew. Chem. Int . Ed. ,2002 , 41 (2) : 275 —277
[20 ] 　Liu S M, Zavalij P Y, Isaacs L. J . Am. Chem. Soc. , 2005 , 127 (48) : 16798 —16799
[21 ] 　Kim K, Samal S , Kumar R N , et al , WO 05P103053 , 2005
[22 ] 　Isaacs L , Park S K, Liu S M, et al . J . Am. Chem. Soc. , 2005 ,127 (51) : 18000 —18001
[23 ] 　Liu S , Kim K, Isaacs L. J . Org. Chem. , 2007 , 72 : 6840 —6847
[24 ] 　Huang W H , Zavalij P Y, Isaacs L. Angew. Chem. Int . Ed. ,2007 , 46 : 7425 —7427
[25 ] 　Kim K, Selvapalam N , Ko H Y, et al . Chem. Soc. Rev. , 2007 ,36 : 267 —279
[26 ] 　Flinn A , Hough G C , Stoddart J F , et al . Angew. Chem. Int . Ed. ,1992 , 31 (11) : 1475 —1477
[27 ] 　Zhao J Z, Kim H J , Oh J , et al . Angew. Chem. Int . Ed. , 2001 ,40 (22) : 4233 —4235
[28 ] 　赵云洁(Zhao Y J ) , 薛赛凤(Xue S F) , 陶朱(Tao Z) 等. 科学通报(Chinese Science Bulletin) , 2004 , 49 (11) : 1046 —1051
[29 ] 　赵云洁(Zhao Y J ) , 薛赛凤(Xue S F) , 陶朱(Tao Z) 等. 化学学报(Acta Chim. Sinica) , 2005 , 63 (10) : 913 —918
[30 ] 　张云黔(Zhang Y Q) , 陶朱(Tao Z) , 赵云洁(Zhao Y J ) 等. 无机化学学报(Chin. J . Inor. Chem. ) , 2005 , 21 (10) : 1576 —1582
[31 ] 　郑利梅(Zheng L M) , 祝黔江(Zhu Q J ) , 陶朱(Tao Z) 等. 无机化学学报(Chin. J . Inor. Chem. ) , 2005 , 21 (10) : 1583 —1588
[32 ] 　郑利梅(Zheng L M) , 朱建男(Zhu J N) , 陶朱(Tao Z) 等. 贵州大学学报(Guizhou Univ. J . ) , 2005 , 22 (2) : 151 —157
[33 ] 　Isobe H , Sato S , Nakamura E. Org. Lett . , 2002 , 4 : 1287 —1289
[34 ] 　Day A I , Arnold A P , Blanch R J . Molecules , 2003 , 8 : 74 —84
[35 ] 　Zhao Y, Xue S , Zhu Q , et al . Chin. Sci . Bull . , 2004 , 49 :1111 —1113
[36 ] 　Lin J X, Zhang Y Q , Tao Z, et al . J . Mol . Sturct . , 2008 , 875 :442 —446
[37 ] 　Jon S Y, Selvapalam N , Kim K, et al . J . Am. Chem. Soc. , 2003 ,125 (34) : 10186 —10187
[38 ] 　尉震(Wei Z) , 林景祥(Lin J X) , 陶朱(Tao Z) 等. 贵州大学学报自然版( Guizhou Univ. J . Nature Sci . ) , 2007 , 24 (3) :313 —317
[39 ] 　Whang D , Jeon YM, Heo J , et al . J . Am. Chem. Soc. ,1996 , 118 (45) : 11333 —11334
[40 ] 　Tuncel D , Steinke J H G. Chem. Commun. , 1999 , 1509 —1511
[41 ] 　Krasia T C , Steinke J H G. Chem. Commun. , 2002 , 22 —23
[42 ] 　Tuncel D , Steinke J H G. Chem. Commun. , 2001 , 253 —254
[43 ] 　Meschke C , Buschmann H J , Schollmeyer E , et al . Macromol .Rapid Commun. , 1998 , 19 : 59 —63
[44 ] 　Meschke C , Buschmann H J , Schollmeyer E. Polymer , 1999 , 40 :945 —949
[45 ] 　Buschmann H J , Wego A , Schollmeyer E , et al . Supramol . Chem. ,2000 , 11 : 225 —227
[46 ] 　Choi S , Lee J W, Ko Y H , Kim K. Macromolecules , 2002 , 35 :3526 —3531
[47 ] 　侯昭升(Hou Z S) , 谭业邦(Tan Y B) , 王成威(Wang C W)等. 高等学校化学学报(Chem. J . Chin. Univ. ) , 2005 , 26 (4) : 773 —777
[48 ] 　Rekharsky M V , Yamamura H , Kawai M, Kim K, et al . Org.Lett . , 2006 , 8 (5) : 815 —818
[49 ] 　Kim S Y, Ka Y H , Kim K, et al . Chem. Asian J . , 2007 , 2 :747 —754
[50 ] 　Huo F J , Yin C X, Yang P. J . Inclusion Phenom. Macrocyclic Chem. , 2006 , 56 : 193 —196
[51 ] 　Tan Y B , Choi S W, Kim K, et al . Macromolecules , 2002 , 35 :7161 —7165
[52 ] 　侯昭升(Hou Z S) , 谭业邦(Tan Y B) , 黄玉玲(Huang YL)等. 高分子学报(Acta Polymerica Sinica) , 2005 , 4 : 491 —495
[53 ] 　侯昭升(Hou Z S) , 谭业邦(Tan Y B) , 黄玉玲(Huang YL)等. 化学学报(Acta Chim. Sinica) , 2005 , 63 (7) : 653 —657
[54 ] 　Choi S W, Ritter H. Macoromol . Rapid Commun. , 2007 , 28 :101 —108
[55 ] 　Liu Y, Ke C F , Zhang H Y, et al . Journal of Organic Chemistry ,2007 , 72 : 280 —283
[56 ] 　侯昭升(Hou Z S) , 谭业邦(Tan YB) , 许静(Xu J ) . 有机化学(Chin. J . Org. Chem. ) , 2005 , 25 (8) : 934 —939
[57 ] 　Liu Y, Li X Y, Zhang H Y, et al . Journal of Organic Chemistry ,2007 , 72 , (10) : 3640 —3645
[58 ] 　Liu Y, Li C J , Guo D S , et al . Supramolecular Chemistry , 2007 ,19 : 517 —523
[59 ] 　张建新(Zhang J X) , 薛赛凤(Xue S F) , 陶朱(Tao Z) 等. 贵州大学学报自然版( Guizhou Univ. J . Nature Sci. ) , 2007 , 24 (2) : 198 —200
[60 ] 　马培华(Ma P H) , 陶朱(Tao Z) , 薛赛凤(Xue S F) 等. 有机化学(Chin. J . Org. Chem. ) , 2007 , 27 (3) : 414 —418
[61 ] 　董南(Dong N) , 薛赛凤(Xue S F) , 陶朱(Tao Z) 等. 化学学报(Acta Chim. Sinica) , 2007 , 65 (11) : 1045 —1050
[62 ] 　张云黔(Zhang YQ) , 肖昕(Xiao X) , 薛赛凤(Xue S F) 等. 贵州大学学报自然版( Guizhou Univ. J . Nature Sci. ) , 2007 , 24 (4) : 404 —406
[63 ] 　Wang R B , Yuan L , Ihmels H , Macartney D H. Chem. Eur. J . ,2007 , 13 : 6468 —6473
[64 ] 　Yuan L , Wang R B , Macartney D H. Tetrahedron : Asymmetry ,2007 , 18 : 483 —487
[65 ] 　Rekharsky M V , Ko Y H , Selvapalam N , Kim K, et al .Supramalecular Chemistry , 2007 , 19 : 39 —46
[66 ] 　Eelkema R , Maeda K, Anderson HL , et al . J . Am. Chem. Soc. ,2007 , 129 : 12384 —12385
[67 ] 　Zhang H Z, Ferrell TA , Dearden D V. International Journal of Mass Spectrometry , 2007 , 265 : 187 —196
[68 ] 　Maddipatla M V S N , Kaanumadle L S , Ramamurthy V , et al .Langmuir , 2007 , 23 : 7545 —7554
[69 ] 　Montes-Navajas P , Corma A , Garcia H. J . Mol . Catal . A:Chemical , 2008 , 279 : 165 —169
[70 ] 　Kim D , Kim E , Kim J , et al . Angew. Chem. Int . Ed. , 2007 , 46 :3471 —3474
[71 ] 　Edmondson S , Huck W T S. Adv. Mater. , 2004 , 16 : 1327 —1328
[72 ] 　Kim K, Jeon W S , Kim D , et al . WO 05P103125 , 2005.
[73 ] 　Kim K, Balaji R , Oh D H , et al . WO 04P072151 , 2004.
[74 ] 　Liu S M, Xu L , Feng Y Q , et al , Talanta , 2004 , 64 (4) : 929 —934
[75 ] 　Nagarajan E R , Oh D H , Kim K, et al . Tetrahedron Lett . , 2006 ,47 : 2073 —2075
[76 ] 　Hwang L , Baek K, Jung M, Kim K, et al . J . Am. Chem. Soc. ,2007 , 129 : 4170 —4171
[77 ] 　李来生(Li L S) , 王上文(Wang S W) , 刘超(Liu C) 等. 化学学报(Acta Chim. Sinica) , 2007 , 65 (17) : 1855 —1862
[78 ] 　Jeon Y J , Kim S Y, Ko Y H , et al . Org. Biomol . Chem. , 2005 , 3 (11) : 2122 —2125
[79 ] 　Choi J , Kim J , Kim K, et al . Chem. Commun. , 2007 , 1151 —1153
[80 ] 　KimJ , Ahn Y, Park K M, et al . Angew. Chem. Int . Ed. , 2007 ,46 : 7393 —7395
[81 ] 　Zhang F , Yajima T, Li Y Z, Chen HL , et al . Angew. Chem. Int .Ed. , 2005 , 4 (22) : 3402 —3407
[82 ] 　丛航(Cong H) , 陶龙玲(Tao L L) , 陶朱(Tao Z) 等. 化学学报(Acta Chim. Sinica) , 2006 , 64 (10) : 989 —996
[83 ] 　傅晓钟(Fu X Z) , 沈祥春(Shen X C) , 黄英(Huang Y) 等. 贵州大学学报(Guizhou Univ. J . ) , 2007 , 24 : 650 —652
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Abstract

Research Progress of Cucurbituril