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

Laurence Raehm; Darren G. Hamilton; Jeremy K. M. Sanders

doi:10.1055/s-2002-34860

ACCOUNT

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

Laurence Raehm^a, 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;

Abstract

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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

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References

1 Frisch HL. Wasserman E. J. Am. Chem. Soc. 1961, 83: 3789

2 Wasserman E. J. Am. Chem. Soc. 1960, 82: 4433

3 Amabilino DB. Stoddart JF. Chem. Rev. 1995, 95: 2725

4 Dietrich-Buchecker CO. Marnot PA. Sauvage JP. Tetrahedron Lett. 1982, 23: 5291

5 Dietrich-Buchecker CO. Sauvage J.-P. Kintzinger JP. Tetrahedron Lett. 1983, 24: 5095

6 Dietrich-Buchecker CO. Sauvage JP. Chem. Rev. 1987, 87: 795

7 Armaroli N. Balzani V. Collin JP. Gavina P. Sauvage JP. Ventura B. J. Am. Chem. Soc. 1999, 121: 4397

8 Dietrich-Buchecker CO. Nierengarten JF. Sauvage J.-P. Tetrahedron Lett. 1992, 33: 3625

9 Carina RF. Dietrich-Buchecker C. Sauvage J.-P. J. Am. Chem. Soc. 1996, 118: 9110

10 Dietrich-Buchecker C. Frommberger B. Luer I. Sauvage J.-P. Vögtle F. Angew. Chem., Int. Ed. Engl. 1993, 32: 1434

11 Dietrich-Buchecker C. Leize E. Nierengarten JF. Sauvage J.-P. Van Dorsselaer A. J. Chem. Soc., Chem. Commun. 1994, 2257

12 Nierengarten JF. Dietrich-Buchecker CO. Sauvage J.-P. New J. Chem. 1996, 20: 685

13 Cardenas DJ. Gavina P. Sauvage J.-P. J. Am. Chem. Soc. 1997, 119: 2656

14 Ibukuro F. Fujita M. Yamaguchi K. Sauvage J.-P.
J. Am. Chem. Soc. 1999, 121: 11014

15 Sauvage J.-P. Acc. Chem. Res. 1998, 31: 611

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

17 Hunter CA. J. Am. Chem. Soc. 1992, 114: 5303

18 Adams H. Carver FJ. Hunter CA. J. Chem. Soc., Chem. Commun. 1995, 809

19 Vögtle F. Meier S. Hoss R. Angew. Chem., Int. Ed. Engl. 1992, 31: 1619

20 Ottenshildebrandt S. Nieger M. Rissanen K. Rouvinen J. Meier S. Harder G. Vögtle F. J. Chem. Soc., Chem. Commun. 1995, 777

21 Vögtle F. Jager R. Handel M. Ottenshildebrandt S. Pure Appl. Chem. 1996, 68: 225

22 Jager R. Vögtle F. Angew. Chem., Int. Ed. Engl. 1997, 36: 930

23 Mohry A. Schwierz H. Vögtle F. Synthesis 1999, 1753

24 Safarowsky O. Nieger M. Frohlich R. Vögtle F. Angew. Chem. Int. Ed. 2000, 39: 1616

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

26 Johnston AG. Leigh DA. Pritchard RJ. Deegan MD. Angew. Chem., Int. Ed. Engl. 1995, 34: 1209

27 Johnston AG. Leigh DA. Nezhat L. Smart JP. Deegan MD. Angew. Chem., Int. Ed. Engl. 1995, 34: 1212

28 Leigh DA. Moody K. Smart JP. Watson KJ. Slawin AMZ. Angew. Chem., Int. Ed. Engl. 1996, 35: 306

29 Leigh DA. Murphy A. Smart JP. Deleuze MS. Zerbetto F. J. Am. Chem. Soc. 1998, 120: 6458

30 Raymo FM. Bartberger MD. Houk KN. Stoddart JF. J. Am. Chem. Soc. 2001, 123: 9264

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

32 Schroff LG. van der Weerdt AJA. Staalman DHJ. Verhoeven JW. de Boer TJ. Tetrahedron Lett. 1973, 1649

33 Borkent JH. Verhoeven JW. de Boer TJ. Chem. Phys. Lett. 1976, 42: 50

34 Lokey RS. Iverson BL. Nature (London) 1995, 375: 303

35 Hamilton DG. Lynch DE. Byriel KA. Kennard CHL. Aust. J. Chem. 1997, 50: 439

36 Dietrich-Buchecker CO. Khemiss A. Sauvage J.-P. J. Chem. Soc., Chem. Commun. 1986, 1376

37 Hamilton DG. Sanders JKM. Davies JE. Clegg W. Teat SJ. Chem. Commun. 1997, 897

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

39 Hamilton DG. Davies JE. Prodi L. Sanders JKM. Chem.-Eur. J. 1998, 4: 608

40 Hamilton DG. Prodi L. Feeder N. Sanders JKM. J. Chem. Soc., Perkin Trans. 1 1999, 1057

41 Hamilton DG. Feeder N. Prodi L. Teat SJ. Clegg W. Sanders JKM. J. Am. Chem. Soc. 1998, 120: 1096

42 Zhang Q. Hamilton DG. Feeder N. Teat SJ. Goodman JM. Sanders JKM. New J. Chem. 1999, 23: 897

43 Hansen JG. Feeder N. Hamilton DG. Gunter MJ. Becher J. Sanders JKM. Org. Lett. 2000, 2: 449

44 Houk KN. Menzer S. Newton SP. Raymo FM. Stoddart JF. Williams DJ. J. Am. Chem. Soc. 1999, 121: 1479

45 Leigh DA. Lusby PJ. Teat SJ. Wilson AJ. Wong JKY. Angew. Chem. Int. Ed. 2001, 40: 1538

46 Yan LZ. Dawson PE. Angew. Chem. Int. Ed. 2001, 40: 3625

47 Wikoff WR. Liljas L. Duda RL. Tsuruta H. Hendrix RW. Johnson JE. Science 2000, 289: 2129

48 Yeh CY. Chang CJ. Nocera DG. J. Am. Chem. Soc. 2001, 123: 1513

49 Yellin RA. Green BS. Knossow M. Rysanek N. Tsoucaris G. J. Inclusion Phenom. 1985, 3: 317

50 Amabilino DB. Ashton PR. Perezgarcia L. Stoddart JF. Angew. Chem., Int. Ed. Engl. 1995, 34: 2378

51 Fujita M. Ibukuro F. Hagihara H. Ogura K. Nature (London) 1994, 367: 720

52 Fujita M. Acc. Chem. Res. 1999, 32: 53

53 Fujita M. Aoyagi M. Ibukuro F. Ogura K. Yamaguchi K. J. Am. Chem. Soc. 1998, 120: 611

54 Fujita M. Fujita N. Ogura K. Yamaguchi K. Nature (London) 1999, 400: 52

55 McArdle CP. Irwin MJ. Jennings MC. Puddephatt RJ. Angew. Chem. Int. Ed. 1999, 38: 3376

56 McArdle CP. Jennings MC. Vittal JJ. Puddephatt RJ. Chem.- Eur. J. 2001, 7: 3572

57 Bilyk A. Harding MM. J. Chem. Soc., Chem. Commun. 1995, 1697

58 Houghton MA. Bilyk A. Harding MM. Turner P. Hambley TW. J. Chem. Soc., Dalton Trans. 1997, 2725

59 Try AC. Harding MM. Hamilton DG. Sanders JKM. Chem. Commun. 1998, 723

60 Grubbs RH. Miller SJ. Fu GC. Acc. Chem. Res. 1995, 28: 446

61 Mohr B. Weck M. Sauvage J.-P. Grubbs RH. Angew. Chem., Int. Ed. Engl. 1997, 36: 1308

62 Dietrich-Buchecker C. Rapenne G. Sauvage JP. Coord. Chem. Rev. 1999, 186: 167

63 Hamilton DG. Feeder N. Teat SJ. Sanders JKM. New J. Chem. 1998, 22: 1019

64 Marsella MJ. Maynard HD. Grubbs RH. Angew. Chem., Int. Ed. Engl. 1997, 36: 1101

65 Hamilton DG. Sanders JKM. Chem. Commun. 1998, 1749

66 Kidd TJ. Leigh DA. Wilson AJ. J. Am. Chem. Soc. 1999, 121: 1599

67 Weidmann JL. Kern JM. Sauvage J.-P. G eerts Y. Muscat D. Mullen L. Chem. Commun. 1996, 1243

68 Muscat D. Kohler W. Rader HJ. Martin K. Mullins S. Muller B. Mullen K. Geerts Y. Macromolecules 1999, 32: 1737

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

70 Menzer S. White AJP. Williams DJ. Belohradsky M. Hamers C. Raymo FM. Shipway AN. Stoddart JF. Macromolecules 1998, 31: 295

71 Simone DL. Swager TM. J. Am. Chem. Soc. 2000, 122: 9300

72 Amabilino DB. Ashton PR. Reder AS. Spencer N. Stoddart JF. Angew. Chem., Int. Ed. Engl. 1994, 33: 1286

73 Amabilino DB. Ashton PR. Boyd SE. Lee JY. Menzer S. Stoddart JF. Williams DJ. Angew. Chem., Int. Ed. Engl. 1997, 36: 2070

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

75 Schwanke F. Safarowsky O. Heim C. Silva G. Vögtle F. Helv. Chim. Acta. 2000, 83: 3279