Subscribe to RSS
DOI: 10.1055/s-2005-872238
Open-Cage Fullerenes: Synthesis, Structure, and Molecular Encapsulation
Publication History
Publication Date:
20 July 2005 (online)
Abstract
The carbon-carbon bond scission of the fullerene cage offers an open-cage fullerene derivative having an opening on the fullerene surface. This account summarizes our recent studies on the syntheses of open-cage C60 derivatives as well as their properties of molecular encapsulation. The photochemical rearrangement of the cyclohexadiene derivative of C60 gives bis(fulleroid), the precursor for the cage scission. The photooxygenative carbon-carbon bond cleavage of bis(fulleroid) affords an open-cage diketone derivative having a 12-membered ring. The reaction of the diketone derivative with aromatic hydrazine or hydrazone allows the ring expansion of the orifice by regioselective cage scission to yield a product bearing a 16-membered ring. The orifice in the product is large enough to pass a hydrogen molecule, producing an endohedral hydrogen complex. In the case of the reaction with ortho-phenylenediamine, two carbon-carbon bonds are sequentially cleaved to afford a product having a 20-membered ring orifice. This product spontaneously encapsulates one water molecule to form an endohedral water complex.
-
1 Introduction
-
2 Preparation of Open-Cage Fullerenes
-
2.1 Bis(fulleroid) Derivatives
-
2.2 Open-Cage Diketone Derivative of C60
-
2.3 Expansion of the Orifice of the Open-Cage Diketone C60 (1) The Reactions with Aromatic Hydrazines or Hydrazones
-
2.4 Expansion of the Orifice of the Open-Cage Diketone C60 (2) The Reactions with Aromatic 1,2-Diamines
-
2.5 Expansion of the Orifice of the Open-Cage Ketolactam C60
-
3 Molecular Structures of the Open-Cage C60 Derivatives
-
4 Molecular Encapsulations in the Open-Cage C60 Derivatives
-
4.1 Hydrogen (H2)
-
4.2 Water
-
5 Conclusion and Future Aspects
Key words
fullerenes - cleavage - ring expansion - host-guest
- 1
Heath JR.O’Brien SC.Zhang Q.Liu Y.Curl RF.Kroto HW.Tittel FK.Smalley RE. J. Am. Chem. Soc. 1985, 107: 7779 - 2
Bethune DS.Johnson RD.Salem JR.de Vries MS.Yannoni CS. Nature 1993, 366: 123 - 3
Endofullerenes. A New Family of Carbon Clusters
Akasaka T.Nagase S. Kluwer Academic Publishers; Dordrecht: 2002. - 4
Fullerenes: Chemistry and Reactions
Hirsch A.Brettreich M. Wiley-VCH; Weinheim: 2005. - 5
Hummelen JC.Prato M.Wudl F. J. Am. Chem. Soc. 1995, 117: 7003 - 6
Birkett PR.Avent AG.Darwish AD.Kroto HW.Taylor R.Walton DRM. J. Chem. Soc., Chem. Commun. 1995, 1869 - 7
Rubin Y. Chem.-Eur. J. 1997, 3: 1009 - 8
Rubin Y. Top. Curr. Chem. 1999, 199: 67 - 9
Hummelen JC.Bellavia-Lund C.Wudl F. Top. Curr. Chem. 1999, 199: 93 - 10
Schick G.Jarrosson T.Rubin Y. Angew. Chem. Int. Ed. 1999, 38: 2360 - 11
Rubin Y.Jarrosson T.Wang G.-W.Bartberger MD.Houk KN.Schick G.Saunders M.Cross RJ. Angew. Chem. Int. Ed. 2001, 40: 1543 - 12
Murata Y.Murata M.Komatsu K. Chem.-Eur. J. 2003, 9: 1600 - 13
Murata Y.Murata M.Komatsu K. J. Am. Chem. Soc. 2003, 125: 7152 - 14
Stanisky CM.Cross RJ.Saunders M.Murata M.Murata Y.Komatsu K. J. Am. Chem. Soc. 2004, 299 - 15
Komatsu K.Murata M.Murata Y. Science 2005, 307: 238 - 16
Brown LD.Itoh K.Suzuki H.Hirai K.Ibers JA. J. Am. Chem. Soc. 1978, 100: 8232 - 17
Inoue H.Yamaguchi H.Suzuki T.Akasaka T.Murata S. Synlett 2000, 1178 - 18
Arce M.-J.Viado AL.An Y.-Z.Khan SI.Rubin Y. J. Am. Chem. Soc. 1996, 118: 3775 - 19
Hsiao T.-Y.Santhosh KC.Liou KF.Cheng C.-H. J. Am. Chem. Soc. 1998, 120: 12232 - 20
Murata Y.Kato N.Komatsu K. J. Org. Chem. 2001, 66: 7235 - 21
Murata Y.Murata M.Komatsu K. J. Org. Chem. 2001, 66: 8187 - 22
Qian W.Bartberger MD.Pastor SJ.Houk KN.Wilkins CL.Rubin Y. J. Am. Chem. Soc. 2000, 122: 8333 - 23
Qian W.Chuang S.-C.Amador RB.Jarrosson T.Sander M.Pieniazek S.Khan SI.Rubin Y. J. Am. Chem. Soc. 2003, 125: 2066 - 24
Iwamatsu S.-i.Vijayalakshmi PS.Hamajima M.Suresh CH.Koga N.Suzuki T.Murata S. Org. Lett. 2002, 4: 1217 - 25
Hsiao T.-Y.Chidambareswaran SK.Cheng C.-H. J. Org. Chem. 1998, 63: 8617 - 26
Janssen RAJ.Hummelen JC.Wudl F. J. Am. Chem. Soc. 1995, 117: 544 - 27
Zimmerman HE.Wu G.-S. Can. J. Chem. 1983, 61: 866 - 28
Suresh CH.Vijayalakshmi PS.Iwamatsu S.-i.Murata S.Koga N. J. Org. Chem. 2003, 68: 3522 - 29
Diederich F.Isaacs L.Philp D. J. Chem. Soc., Perkin Trans. 2 1994, 391 - 30
Hall MH.Lu H.Shevlin PB. J. Am. Chem. Soc. 2001, 123: 1349 - 31
Inoue H.Yamaguchi H.Iwamatsu S.-i.Uozaki T.Suzuki T.Akasaka T.Nagase S.Murata S. Tetrahedron Lett. 2001, 42: 895 - 32
Murata Y.Komatsu K. Chem. Lett. 2001, 30: 896 - 33
Arbogast JW.Darmanyan AP.Foote CS.Diederich FN.Whetten RL.Rubin Y.Alvarez MM.Anz SJ. J. Phys. Chem. 1991, 95: 11 - 34
Arbogast JW.Foote CS. J. Am. Chem. Soc. 1991, 113: 8886 - 35
Tokuyama H.Nakamura E. J. Org. Chem. 1994, 59: 1135 - 36
Creegan KM.Robbins JL.Robbins WK.Millar JM.Sherwood RD.Tindall PJ.Cox Smith AB.McCauley JP.Jones DR.Gallagher RT. J. Am. Chem. Soc. 1992, 114: 1103 - 37
Tsyboulski D.Heymann D.Bachilo SM.Alemany LB.Weisman RB. J. Am. Chem. Soc. 2004, 126: 7350 - 38
Komatsu K.Murata Y. Chemistry 2004, 59 (2): 23 - 39
Iwamatsu S.-i.Ono F.Murata S. Chem. Commun. 2003, 1268 - 40
Chen Z.-X.Wang G.-W. J. Org. Chem. 2005, 70: 2380 - 41
Soliman FM.Yakout E.-SM.Said MM. Bull. Chem. Soc. Jpn. 1994, 67: 2162 - 42
Kuder JE. Tetrahedron 1972, 28: 1973 - 43
Iwamatsu S.-i.Kuwayama T.Kobayashi K.Nagase S.Murata S. Synthesis 2004, 2962 - 44
Kimura T.Minabe M.Suzuki K. J. Org. Chem. 1978, 43: 1247 - 45
Iwamatsu S.-i.Uozaki T.Kobayashi K.Suyong R.Nagase S.Murata S. J. Am. Chem. Soc. 2004, 126: 2668 - 46
Hummelen JC.Knight B.Pavlovich J.González R.Wudl F. Science 1995, 269: 1554 - 47
Iwamatsu S.-i.Ono F.Murata S. Chem. Lett. 2003, 32: 614 - 48
Iwamatsu S.-i.Murata S. Tetrahedron Lett. 2004, 45: 6391 - 49
Vougioukalakis GC.Prassides K.Campanera JM.Heggie MI.Orfanopoulos M. J. Org. Chem. 2004, 69: 4524 - 50
Vougioukalakis GC.Prassides K.Orfanopoulos M. Org. Lett. 2004, 6: 1245 - 51
Iwamatsu S.-i.Murata S.Andoh Y.Minoura M.Kobayashi K.Mizorogi N.Nagase S. J. Org. Chem. 2005, 70: 4820 - 52
Sternfeld T.Saunders M.Cross RJ.Rabinovitz M. Angew. Chem. Int. Ed. 2003, 42: 3136 - 53
Williams CI.Whiehead MA.Pang L. J. Phys. Chem. 1993, 97: 11652 - 54
Maniwa Y.Kataura H.Abe M.Suzuki S.Achiba Y.Kira H.Matsuda K. J. Phys. Soc. Jpn. 2002, 71: 2863 - 55
Kolesnikov AI.Zanotti J.-M.Loong C.-K.Thiyagarajan P.Moravsky AP.Loutfy RO.Burnham CJ. Phys. Rev. Lett. 2004, 93: 035503 - 56
Syamala MS.Cross RJ.Saunders M. J. Am. Chem. Soc. 2002, 124: 6216 - 57
Stackow R.Schick G.Jarrosson T.Rubin Y.Foote CS. J. Phys. Chem. B 2000, 104: 7914 - 58
Oberdörster E. Environ Health Perspect. 2004, 112: 1058 - 59
Sayes CM.Fortner JD.Guo W.Lyon D.Boyd AM.Ausman KD.Tao YJ.Sitharaman B.Wilson LJ.Hughes JB.West JL.Colvin VL. Nano Lett. 2004, 4: 1881