Download PDF
Synlett 2002(11): 1743-1761  
DOI: 10.1055/s-2002-34860
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

From Kinetic to Thermodynamic Assembly of Catenanes: Error Checking, Supramolecular Protection and Oligocatenanes

Laurence Raehma, Darren G. Hamilton*b, Jeremy K. M. Sanders*a
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK
e-Mail: jkms@cam.ac.uk;
Department of Chemistry, Mount Holyoke College, South Hadley, Massachusetts 01075, USA
e-Mail: hamilton@mtholyoke.edu;
Further Information

Publication History

Received 7 January 2002
Publication Date:
21 October 2002 (online)

    Permissions and Reprints All articles of this category

Abstract

Catenanes are molecules comprising at least two mechanically interlocked rings: they cannot be separated, yet do not possess covalent links between ring constituents. Over the last two decades several efficient templating mechanisms for the assembly of catenanes, and other topologically complex molecules, have been developed and exploited in the synthesis of numerous systems, often with impressive efficiency. Kinetically controlled assembly routes, employing transition metal complexation or amide hydrogen bonding interactions, have proved tremendously successful. A third arena of investigation, and perhaps the most thoroughly explored and exploited, is the utilisation of π-complementary components, principally bipyridinium dications and aromatic ethers. In our work electron deficient bipyridinium dications were replaced with uncharged, yet electron accepting, aromatic diimides. This replacement permitted the use of a variety of ring closing reactions for catenane formation by allowing us to step away from the structurally powerful but ultimately limited chemistry demanded by bipyridinium systems. A total of four ring-closing reactions were employed: acetylenic coupling, Mitsunobu alkylation, Grubbs’ alkene metathesis, and zinc(II)-bipyridyl ligation. The first three methods yielded fully covalent interlocked systems, the fourth a catenane containing a metallomacrocycle. The first two methods employed irreversible bond forming reactions in catenane formation, the latter two thermodynamically controlled processes.

This flexible system of interacting components, the synthetic chemistry used in their preparation, and the structural flexibility offered by the combination of these factors, is discussed in terms of a series of model systems leading to the proposition of a method for the synthesis of a polycatenane. Such systems, polymeric chains of interlocked rings, are unrealised yet coveted goals of chemists working in the area of supramolecular topology and are predicted to exhibit valuable and unusual material properties.

Key words

catenanes - supramolecular chemistry - templating - self-assembly - thermodynamic control

    References

  • 1 Frisch HL. Wasserman E. J. Am. Chem. Soc.  1961,  83:  3789 
    CrossrefGoogle Scholar
  • 2 Wasserman E. J. Am. Chem. Soc.  1960,  82:  4433 
    CrossrefGoogle Scholar
  • 3 Amabilino DB. Stoddart JF. Chem. Rev.  1995,  95:  2725 
    CrossrefGoogle Scholar
  • 4 Dietrich-Buchecker CO. Marnot PA. Sauvage JP. Tetrahedron Lett.  1982,  23:  5291 
    CrossrefGoogle Scholar
  • 5 Dietrich-Buchecker CO. Sauvage J.-P. Kintzinger JP. Tetrahedron Lett.  1983,  24:  5095 
    CrossrefGoogle Scholar
  • 6 Dietrich-Buchecker CO. Sauvage JP. Chem. Rev.  1987,  87:  795 
    CrossrefGoogle Scholar
  • 7 Armaroli N. Balzani V. Collin JP. Gavina P. Sauvage JP. Ventura B. J. Am. Chem. Soc.  1999,  121:  4397 
    CrossrefGoogle Scholar
  • 8 Dietrich-Buchecker CO. Nierengarten JF. Sauvage J.-P. Tetrahedron Lett.  1992,  33:  3625 
    CrossrefGoogle Scholar
  • 9 Carina RF. Dietrich-Buchecker C. Sauvage J.-P. J. Am. Chem. Soc.  1996,  118:  9110 
    CrossrefGoogle Scholar
  • 10 Dietrich-Buchecker C. Frommberger B. Luer I. Sauvage J.-P. Vögtle F. Angew. Chem., Int. Ed. Engl.  1993,  32:  1434 
    Google Scholar
  • 11 Dietrich-Buchecker C. Leize E. Nierengarten JF. Sauvage J.-P. Van Dorsselaer A. J. Chem. Soc., Chem. Commun.  1994,  2257 
    CrossrefGoogle Scholar
  • 12 Nierengarten JF. Dietrich-Buchecker CO. Sauvage J.-P. New J. Chem.  1996,  20:  685 
    Google Scholar
  • 13 Cardenas DJ. Gavina P. Sauvage J.-P. J. Am. Chem. Soc.  1997,  119:  2656 
    CrossrefGoogle Scholar
  • 14 Ibukuro F. Fujita M. Yamaguchi K. Sauvage J.-P.
    J. Am. Chem. Soc.  1999,  121:  11014 
    CrossrefGoogle Scholar
  • 15 Sauvage J.-P. Acc. Chem. Res.  1998,  31:  611 
    CrossrefGoogle Scholar
  • 16 Cardenas DJ. Collin JP. Gavina P. Sauvage J.-P. De Cian A. Fischer J. Armaroli N. Flamigni L. Vicinelli V. Balzani V. J. Am. Chem. Soc.  1999,  121:  5481 
    CrossrefGoogle Scholar
  • 17 Hunter CA. J. Am. Chem. Soc.  1992,  114:  5303 
    CrossrefGoogle Scholar
  • 18 Adams H. Carver FJ. Hunter CA. J. Chem. Soc., Chem. Commun.  1995,  809 
    CrossrefGoogle Scholar
  • 19 Vögtle F. Meier S. Hoss R. Angew. Chem., Int. Ed. Engl.  1992,  31:  1619 
    Google Scholar
  • 20 Ottenshildebrandt S. Nieger M. Rissanen K. Rouvinen J. Meier S. Harder G. Vögtle F. J. Chem. Soc., Chem. Commun.  1995,  777 
    CrossrefGoogle Scholar
  • 21 Vögtle F. Jager R. Handel M. Ottenshildebrandt S. Pure Appl. Chem.  1996,  68:  225 
    Google Scholar
  • 22 Jager R. Vögtle F. Angew. Chem., Int. Ed. Engl.  1997,  36:  930 
    Google Scholar
  • 23 Mohry A. Schwierz H. Vögtle F. Synthesis  1999,  1753 
    Article in Thieme ConnectGoogle Scholar
  • 24 Safarowsky O. Nieger M. Frohlich R. Vögtle F. Angew. Chem. Int. Ed.  2000,  39:  1616 
    CrossrefGoogle Scholar
  • 25 Li QY. Vogel E. Parham AH. Nieger M. Bolte M. Frohlich R. Saarenketo P. Rissanen K. Vögtle F. Eur. J. Org. Chem.  2001,  4041 
    CrossrefGoogle Scholar
  • 26 Johnston AG. Leigh DA. Pritchard RJ. Deegan MD. Angew. Chem., Int. Ed. Engl.  1995,  34:  1209 
    Google Scholar
  • 27 Johnston AG. Leigh DA. Nezhat L. Smart JP. Deegan MD. Angew. Chem., Int. Ed. Engl.  1995,  34:  1212 
    Google Scholar
  • 28 Leigh DA. Moody K. Smart JP. Watson KJ. Slawin AMZ. Angew. Chem., Int. Ed. Engl.  1996,  35:  306 
    Google Scholar
  • 29 Leigh DA. Murphy A. Smart JP. Deleuze MS. Zerbetto F. J. Am. Chem. Soc.  1998,  120:  6458 
    CrossrefGoogle Scholar
  • 30 Raymo FM. Bartberger MD. Houk KN. Stoddart JF. J. Am. Chem. Soc.  2001,  123:  9264 
    CrossrefGoogle Scholar
  • 31 Ashton PR. Goodnow TT. Kaifer AE. Reddington MV. Slawin AMZ. Spencer N. Stoddart JF. Vicent C. Williams DJ. Angew. Chem., Int. Ed. Engl.  1989,  28:  1396 
    Google Scholar
  • 32 Schroff LG. van der Weerdt AJA. Staalman DHJ. Verhoeven JW. de Boer TJ. Tetrahedron Lett.  1973,  1649 
    CrossrefGoogle Scholar
  • 33 Borkent JH. Verhoeven JW. de Boer TJ. Chem. Phys. Lett.  1976,  42:  50 
    CrossrefGoogle Scholar
  • 34 Lokey RS. Iverson BL. Nature (London)  1995,  375:  303 
    CrossrefGoogle Scholar
  • 35 Hamilton DG. Lynch DE. Byriel KA. Kennard CHL. Aust. J. Chem.  1997,  50:  439 
    Google Scholar
  • 36 Dietrich-Buchecker CO. Khemiss A. Sauvage J.-P. J. Chem. Soc., Chem. Commun.  1986,  1376 
    CrossrefGoogle Scholar
  • 37 Hamilton DG. Sanders JKM. Davies JE. Clegg W. Teat SJ. Chem. Commun.  1997,  897 
    CrossrefGoogle Scholar
  • 38 Anelli PL. Ashton PR. Ballardini R. Balzani V. Delgado M. Gandolfi MT. Goodnow TT. Kaifer AE. Philp D. Pietraszkiewicz M. Prodi L. Reddington MV. Slawin AMZ. Spencer N. Stoddart JF. Vicent C. Williams DJ. J. Am. Chem. Soc.  1992,  114:  193 
    CrossrefGoogle Scholar
  • 39 Hamilton DG. Davies JE. Prodi L. Sanders JKM. Chem.-Eur. J.  1998,  4:  608 
    Google Scholar
  • 40 Hamilton DG. Prodi L. Feeder N. Sanders JKM. J. Chem. Soc., Perkin Trans. 1  1999,  1057 
    CrossrefGoogle Scholar
  • 41 Hamilton DG. Feeder N. Prodi L. Teat SJ. Clegg W. Sanders JKM. J. Am. Chem. Soc.  1998,  120:  1096 
    CrossrefGoogle Scholar
  • 42 Zhang Q. Hamilton DG. Feeder N. Teat SJ. Goodman JM. Sanders JKM. New J. Chem.  1999,  23:  897 
    CrossrefGoogle Scholar
  • 43 Hansen JG. Feeder N. Hamilton DG. Gunter MJ. Becher J. Sanders JKM. Org. Lett.  2000,  2:  449 
    CrossrefGoogle Scholar
  • 44 Houk KN. Menzer S. Newton SP. Raymo FM. Stoddart JF. Williams DJ. J. Am. Chem. Soc.  1999,  121:  1479 
    CrossrefGoogle Scholar
  • 45 Leigh DA. Lusby PJ. Teat SJ. Wilson AJ. Wong JKY. Angew. Chem. Int. Ed.  2001,  40:  1538 
    CrossrefGoogle Scholar
  • 46 Yan LZ. Dawson PE. Angew. Chem. Int. Ed.  2001,  40:  3625 
    CrossrefGoogle Scholar
  • 47 Wikoff WR. Liljas L. Duda RL. Tsuruta H. Hendrix RW. Johnson JE. Science  2000,  289:  2129 
    CrossrefGoogle Scholar
  • 48 Yeh CY. Chang CJ. Nocera DG. J. Am. Chem. Soc.  2001,  123:  1513 
    CrossrefGoogle Scholar
  • 49 Yellin RA. Green BS. Knossow M. Rysanek N. Tsoucaris G. J. Inclusion Phenom.  1985,  3:  317 
    CrossrefGoogle Scholar
  • 50 Amabilino DB. Ashton PR. Perezgarcia L. Stoddart JF. Angew. Chem., Int. Ed. Engl.  1995,  34:  2378 
    Google Scholar
  • 51 Fujita M. Ibukuro F. Hagihara H. Ogura K. Nature (London)  1994,  367:  720 
    CrossrefGoogle Scholar
  • 52 Fujita M. Acc. Chem. Res.  1999,  32:  53 
    CrossrefGoogle Scholar
  • 53 Fujita M. Aoyagi M. Ibukuro F. Ogura K. Yamaguchi K. J. Am. Chem. Soc.  1998,  120:  611 
    CrossrefGoogle Scholar
  • 54 Fujita M. Fujita N. Ogura K. Yamaguchi K. Nature (London)  1999,  400:  52 
    CrossrefGoogle Scholar
  • 55 McArdle CP. Irwin MJ. Jennings MC. Puddephatt RJ. Angew. Chem. Int. Ed.  1999,  38:  3376 
    CrossrefGoogle Scholar
  • 56 McArdle CP. Jennings MC. Vittal JJ. Puddephatt RJ. Chem.- Eur. J.  2001,  7:  3572 
    CrossrefGoogle Scholar
  • 57 Bilyk A. Harding MM. J. Chem. Soc., Chem. Commun.  1995,  1697 
    CrossrefGoogle Scholar
  • 58 Houghton MA. Bilyk A. Harding MM. Turner P. Hambley TW. J. Chem. Soc., Dalton Trans.  1997,  2725 
    CrossrefGoogle Scholar
  • 59 Try AC. Harding MM. Hamilton DG. Sanders JKM. Chem. Commun.  1998,  723 
    CrossrefGoogle Scholar
  • 60 Grubbs RH. Miller SJ. Fu GC. Acc. Chem. Res.  1995,  28:  446 
    CrossrefGoogle Scholar
  • 61 Mohr B. Weck M. Sauvage J.-P. Grubbs RH. Angew. Chem., Int. Ed. Engl.  1997,  36:  1308 
    Google Scholar
  • 62 Dietrich-Buchecker C. Rapenne G. Sauvage JP. Coord. Chem. Rev.  1999,  186:  167 
    CrossrefGoogle Scholar
  • 63 Hamilton DG. Feeder N. Teat SJ. Sanders JKM. New J. Chem.  1998,  22:  1019 
    CrossrefGoogle Scholar
  • 64 Marsella MJ. Maynard HD. Grubbs RH. Angew. Chem., Int. Ed. Engl.  1997,  36:  1101 
    CrossrefGoogle Scholar
  • 65 Hamilton DG. Sanders JKM. Chem. Commun.  1998,  1749 
    CrossrefGoogle Scholar
  • 66 Kidd TJ. Leigh DA. Wilson AJ. J. Am. Chem. Soc.  1999,  121:  1599 
    CrossrefGoogle Scholar
  • 67 Weidmann JL. Kern JM. Sauvage J.-P. G eerts Y. Muscat D. Mullen L. Chem. Commun.  1996,  1243 
    CrossrefGoogle Scholar
  • 68 Muscat D. Kohler W. Rader HJ. Martin K. Mullins S. Muller B. Mullen K. Geerts Y. Macromolecules  1999,  32:  1737 
    CrossrefGoogle Scholar
  • 69 Weidmann JL. Kern JM. Sauvage JP. Muscat D. Mullins S. Kohler W. Rosenauer C. Rader HJ. Martin K. Geerts Y. Chem.-Eur. J.  1999,  5:  1841 
    Google Scholar
  • 70 Menzer S. White AJP. Williams DJ. Belohradsky M. Hamers C. Raymo FM. Shipway AN. Stoddart JF. Macromolecules  1998,  31:  295 
    CrossrefGoogle Scholar
  • 71 Simone DL. Swager TM. J. Am. Chem. Soc.  2000,  122:  9300 
    CrossrefGoogle Scholar
  • 72 Amabilino DB. Ashton PR. Reder AS. Spencer N. Stoddart JF. Angew. Chem., Int. Ed. Engl.  1994,  33:  1286 
    CrossrefGoogle Scholar
  • 73 Amabilino DB. Ashton PR. Boyd SE. Lee JY. Menzer S. Stoddart JF. Williams DJ. Angew. Chem., Int. Ed. Engl.  1997,  36:  2070 
    Google Scholar
  • 74 Amabilino DB. Ashton PR. Balzani V. Boyd SE. Credi A. Lee JY. Menzer S. Stoddart JF. Venturi M. Williams DJ. J. Am. Chem. Soc.  1998,  120:  4295 
    CrossrefGoogle Scholar
  • 75 Schwanke F. Safarowsky O. Heim C. Silva G. Vögtle F. Helv. Chim. Acta.  2000,  83:  3279 
    CrossrefGoogle Scholar