中文
Announcement
More
Progress in Chemistry 2008, Vol. 20 Issue (06): 909-917 Previous Articles   Next Articles

• Review •

Exohedral Functionalization of Endohedral Metallofullerenes

Lian Yongfu1** Yuan Fulong1 Guo Lihua2 Liu Meiling1   

  1. 1.College of chemistry chemical engnerring and Materials, Heilongjiang University, Harbin 150083, China; 2.Faculty of Physics and Chemistry, Harbin Normal University, Harbin 150080, China)
  • Received: Revised: Online: Published:
  • Contact: Lian Yongfu
PDF ( 2000 ) Cited
Export

EndNote

Ris

BibTeX

Owning to their unique structures and novel properties, Endohedral metallofullerenes, i.e. fullerenes with metallic species inside the hollow cage, have attracted much attention of chemists, physicists and even biologists. With the rapid improvement of metallofullerenes chemistry, exohedral functionalization is proven to be essential to determine the structure and property of metallofullerenes and to broaden their applications in various fields. Based on the classification of interaction and chemical reaction by nature, the development of exohedral functionalization of metallofullerenes in recent years is comprehensively reviewed, including cycloaddion reaction, self-assembly with crown ethers, singly bonded derivatives, water-soluble derivatives and filling of single-walled carbon nanotubes, etc. The potential applications of functionalized metallofullerenes are also remarked, and the future prospects for exohedral functionalization of metallofullerenes are presented.

CLC Number: 

[ 1 ] Kroto H W, Heath J , O’Brien S C , et al . Nature , 1985 , 318 :162 —164
[ 2 ] Kratschmer W, Lamb L D , Fostiropoulos K, et al . Nature , 1990 ,347 : 354 —358
[ 3 ] Akasaka T , Nagase S. Endofullerenes : A New Family of Carbon Clusters. Dordrecht : Kluwer , 2002
[ 4 ] Shinohara H. Rep. Prog. Phys. , 2000 , 63 : 843 —892
[ 5 ] Heath J , O’Brien S , Zhang Q , et al . J . Am. Chem. Soc. ,1985 , 107 : 7779 —7780
[ 6 ] Chai Y, Guo T , Jin C , et al . J . Phys. Chem. , 1991 , 95 :7564 —7568
[ 7 ] Suzuki T , Kikuchi K, Oguri F , et al . Tetrahedron , 1996 , 52 :4973 —4982
[ 8 ] Mikawa M, Kato H , Okumura M, et al . Bioconjugate Chem. ,2001 , 12 : 510 —514
[ 9 ] Cagle D W, Kennel S J , Mirzadeh S , et al . Proc. Natl . Acad.Sci . USA , 1999 , 96 : 5182 —5187
[10] Akasaka T , Kato T , Kobayashi K, et al . Nature , 1995 , 374 :600 —601
[11] Akasaka T , Kato T , Kobayashi K, et al . Angew. Chem. Int .Ed. Engl . , 1995 , 34 : 2139 —2141
[12] Yamada M, Feng L , Wakahara T , et al . J . Phys. Chem. B ,2005 , 109 : 6049 —6051
[13] Wakahara T , Kobayashi J , Yamada M, et al . J . Am. Chem.Soc. , 2004 , 126 : 4883 —4887
[14] Yamada M, Nakahodo T , Wakahara T , et al . J . Am. Chem.Soc. , 2005 , 127 : 14570 —14571
[15] Iiduka Y, Ikenaga O , Sakuraba A , et al . J . Am. Chem. Soc. ,2005 , 127 : 9956 —9957
[16] Wakahara T , Iiduka Y, Ikenaga O , et al . J . Am. Chem. Soc. ,2006 , 128 : 9919 —9925
[17] Akasaka T , Nagase S , Kobayashi K, et al . J . Syth. Organ.Chem. Jpn. , 1996 , 54 : 580 —585
[18] Akasaka T , Kato T , Nagase S. Tetrahedron , 1996 , 52 : 5015 —5020
[19] Suzuki T , Maruyama Y, Kato T , et al . J . Am. Chem. Soc. ,1995 , 117 : 9606 —9607
[20] Feng L , Zhang X, Yu Z , et al . Chem. Mater. , 2002 , 14 :4021 —4023
[21] Maeda Y, Matsunaga Y, Wakahara T , et al . J . Am. Chem.Soc. , 2004 , 126 : 6858 —6859
[22] Lu X, Xu J X, He X R , et al . Chem. Mater. , 2004 , 16 : 953 —955
[23] Nikawa H , Kikuchi T , Wakahara T , et al . J . Am. Chem. Soc. ,2005 , 127 : 9684 —9685
[24] Wakahara T , Nikawa H , Kikuchi T , et al . J . Am. Chem. Soc. ,2006 , 128 : 14228 —14229
[25] Tagmatarchis N , Taninaka A , Shinohara H. Chem. Phys. Lett . ,2002 , 355 : 226 —232
[26] Goryunkov A A , Markov V Y, Ioffe I N , et al . Angew. Chem.Int . Ed. Engl . , 2004 , 43 : 997 —1000
[27] Kareev I , Lebedkin S , Bubnov V , et al . Angew. Chem. Int .Ed. Engl . , 2005 , 44 : 1846 —1849
[28] Schlueter J A , Seaman J M, Taha S , et al . J . Chem. Soc.Chem. Commun. , 1993 , 972 —974
[29] Komatsu K, Murata Y, Sugita N , et al Tetrahedron Lett . , 1993 ,34 : 8473 —8476
[30] Rotello V M, Howard J B , Yadev T , et al Tetrahedron Lett . ,1993 , 34 : 1561 —1562
[31] Iezzi E , Duchamp J , Harich K, et al . J . Am. Chem. Soc. ,2002 , 124 : 525 —526
[32] Lee H , Olmstead M, Iezzi E , et al . J . Am. Chem. Soc. , 2002 ,124 : 3494 —3495
[33] Stevenson S , Stephen R , Amos T , J . Am. Chem. Soc. , 2005 ,127 : 12776 —12777
[34] Maeda Y, Miyashita J , Hasegawa T , et al . J . Am. Chem. Soc. ,2005 , 127 : 12190 —12191
[35] Bolskar R , Benedetto A , Husebo L , et al . J . Am. Chem. Soc. ,2003 , 125 : 5471 —5478
[36] Cardona C M, Kitaygorodskiy A , Echegoyen L , J . Am. Chem.Soc. , 2005 , 127 : 10448 —10453
[37] Feng L , Nakahodo T , Wakahara T , et al . J . Am. Chem. Soc. ,2005 , 127 : 17136 —17137
[38] Feng L , Wakahara T , Nakahodo T , et al . Chem. Euro. J . ,2006 , 12 : 5578 —5586
[39] Feng L , Tsuchiya T , Wakahara T , et al . J . Am. Chem. Soc. ,2006 , 128 : 5990 —5991
[40] Ocfrain M, Herranz M A , Maex L , et al . Chem. Euro. J . ,2003 , 9 : 4811 —4819
[41] Maggini M, Scorrano G, Prato M. J . Am. Chem. Soc. , 1993 ,115 : 9798 —9799
[42] Cao B P , Wakahara T , Maeda Y, et al . Chem. Euro. J . , 2004 ,10 : 716 —720
[43] Lu X, He X R , Feng L , et al . Tetrahedron , 2004 , 60 : 3713 —3716
[44] Feng L , Lu X, He X R , et al . Inor. Chem. Commun. , 2004 ,7 : 1010 —1013
[45] Yamada M, Wakahara T , Nakahodo , et al . J . Am. Chem. Soc. ,2006 , 128 : 1402 —1403
[46] Cardona C M, Kitaygorodskiy A , Ortiz A. J . Org. Chem. ,2005 , 70 : 5092 —5097
[47] Cai T , Ge Z X, Iezzi E B , et al . Chem. Commun. , 2006 ,3594 —3596
[48] Cai T , Slebodnick C , Xu L S , et al . J . Am. Chem. Soc. ,2006 , 128 : 6486 —6492
[49] Chen N , Zhang E Y, Tan K, et al . Org. Lett . , 2007 , 9 :2011 —2013
[50] Martin N , Altable M, Filippone S , et al . Angew. Chem. Int .Ed. Engl . , 2006 , 45 : 110 —114
[51] Atwood J L , Koutsantonis GA , Raston CL. Nature , 1994 , 368 :229 —231
[52] Suzuki T , Nakashina K, Shinkai S. Chem. Lett . 1994 , 699 —702
[53] Yang S F , Yang S H. Langmuir , 2002 , 18 : 8488 —8495
[54] Tsuchiya T , Sato K, Kurihara H , et al . J . Am. Chem. Soc. ,2006 , 128 : 6699 —6703
[55] Smith B W, Monthioux M, Luzzi D E. Nature , 1998 , 396 :323 —324
[56] Luzzi D E , Smith B W. Chem. Phys. Lett . , 2000 , 321 : 169 —174
[57] Guan L H , Li HJ , Shi ZJ , et al . Solid State Commun. , 2005 ,133 —136
[58] Hirahara K, Suenaga K, Bandow S , et al . Phys. Rev. Lett . ,2000 , 85 : 5384 —5387
[59] Sun B Y, Inoue T , Shimada T , et al . J . Phys. Chem. B , 2004 ,18 : 9011 —9015
[60] Suenaga K, Okazaki T , Hirahara K, et al . Appl . Phys. A ,2003 , 76 : 445 —447
[61] Chiu P W, Yang S F , Yang S H , et al . Appl . Phys. A , 2003 ,76 : 463 —467
[62] Lee J , Kim H , Kahng S J , et al . Nature , 2002 , 415 : 1005 —1008
[63] Cagle D , Thrash T , Alford M, et al . J . Am. Chem. Soc. ,1996 , 118 : 8043 —8047
[64] Kato H , Kanazawa Y, Okumura M, et al . J . Am. Chem. Soc. ,2003 , 125 : 4391 —4397
[65] Zhang S , Sun D , Li X, et al . Full . Sci . Tech. , 1997 , 5 (7) :1635 —1638
[66] Stevenson S , Burbank P , Harich K, et al . J . Phys. Chem. A ,1998 , 102 : 2833 —2837
[67] Sun D , Huang H , Yang S. Chem. Mater. , 1999 , 11 : 374 —377
[68] Zhang Y Z , Xiang J F , Zhuang J P , et al . Chem. Lett . , 2005 ,34 : 1264 —1265
[69] 孙宝云(Sun B Y) , 顾镇南( Gu Z N) , 高等学校化学学报(Chem. J . Chinese Univ. ) , 2003 , 24 : 1747 —1749
[70] Shu C Y, Gan L H , Wang C R , et al . Carbon , 2006 , 44 : 496 —500
[71] 卢兴(Lu X) , 徐建勋(Xu J X) , 施祖进(Shi ZJ) 等. 高等学校化学学报(Chem. J . Chinese Univ. ) , 2005 , 25 : 697 —700
[72] Shu C Y, Zhang E Y, Xiang J F , et al . J . Phys. Chem. B ,2006 , 110 : 15597 —15601
[73] Lu X, He X R , Feng L , et al . Inor. Chim. Acta , 2004 , 357 :2397 —2400
[74] Iezzi EB , Duchamp J C , Fletcher KR , et al . Nano Lett . , 2002 ,2 : 1187 —1190
[75] Gu G, Huang HJ , Yang S H , et al . Chem. Phys. Lett . , 1998 ,289 : 167 —173
[76] Funasaka H , Sugiyama K, Yamamoto K, et al . J . Phys. Chem. ,1995 , 99 : 1826 —1830
[77] Cram D J , CramJ M. Science , 1974 , 183 : 803 —809
[78] Kyba E , Helgeson R C , Madan K, et al . J . Am. Chem. Soc. ,1977 , 99 : 2564 —2571
[79] Lian Y F , Shi Z J , Zhou X H , et al . Chem. Mater. , 2001 , 13 :39 —42

[1] Ruyue Cao, Jingjing Xiao, Yixuan Wang, Xiangyu Li, Anchao Feng, Liqun Zang. Cascade RAFT Polymerization of Hetero Diels-Alder Cycloaddition Reaction [J]. Progress in Chemistry, 2023, 35(5): 721-734.
[2] Jun Dong, Jiaxi Xu. An Overview on the Synthesis and Reactions of Sulfines [J]. Progress in Chemistry, 2022, 34(5): 1088-1108.
[3] Liao Yiming, Wu Baoqi, Tang Rongzhi, Lin Feng, Tan Yu. Strain-Promoted Azide-Alkyne Cycloaddition [J]. Progress in Chemistry, 2022, 34(10): 2134-2145.
[4] Di Zeng, Xuechen Liu, Yuanyi Zhou, Haipeng Wang, Ling Zhang, Wenzhong Wang. Renewable Aromatic Production from Biomass-Derived Furans [J]. Progress in Chemistry, 2022, 34(1): 131-141.
[5] Lei Wu, Lihui Liu, Shufen Chen. Flexible Organic Light-Emitting Diodes Using Carbon-Based Transparent Electrodes [J]. Progress in Chemistry, 2021, 33(5): 802-817.
[6] Qiang Zhang, Wenjun Huang, Yanbin Wang, Xingjian Li, Yiheng Zhang. Functionalization of Polyurethane Based on Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction [J]. Progress in Chemistry, 2020, 32(2/3): 147-161.
[7] Yangrong Yao, Suyuan Xie. Structures and Progress of Carbon Clusters [J]. Progress in Chemistry, 2019, 31(1): 50-62.
[8] Zhicheng Fu, Jiaxi Xu*. Synthesis of Azetidines [J]. Progress in Chemistry, 2018, 30(8): 1047-1066.
[9] Qi-Feng Zhou, Bo Jiang*, Hai-Bo Yang*. Design and Synthesis of Conjugated Aromatic Macrocyclic Rings That Can Serve as Carbon Nanotube Segments [J]. Progress in Chemistry, 2018, 30(5): 628-638.
[10] Xiaolei Gong, Wenchao Gao, Honghong Chang, Wenlong Wei*, Xing Li*. The Research in Cycloaddition Reactions of Allenic Compounds [J]. Progress in Chemistry, 2017, 29(11): 1331-1350.
[11] Wan Xiaomei, Zhang Chuan, Yu Dinghua, Huang He, Hu Yi. Enzyme Immobilized on Carbon Nanotubes [J]. Progress in Chemistry, 2015, 27(9): 1251-1259.
[12] Song Chengjie, Wang Erjing, Dong Binghai, Wang Shimin. Non-Fullerene Organic Small Molecule Acceptor Materials [J]. Progress in Chemistry, 2015, 27(12): 1754-1763.
[13] Zhu Jin, Lou Zimo, Wang Zhuoxing, Xu Xinhua. Preparation of Iron and Manganese Oxides/Carbon Composite Materials for Arsenic Removal from Aqueous Solution [J]. Progress in Chemistry, 2014, 26(09): 1551-1561.
[14] Li Yuda, Wang Xunchang, Lv Renliang, Wang Feng. Non-Covalent Separation of Optically Active Single-Walled Carbon Nanotubes [J]. Progress in Chemistry, 2014, 26(08): 1361-1368.
[15] Li Jian, Guan Yibiao, Fu Kai, Su Yuefeng, Bao Liying, Wu Feng. Applications of Carbon Nanotubes and Graphene in the Energy Storage Batteries [J]. Progress in Chemistry, 2014, 26(07): 1233-1243.