Synthesis, structure and photophysics of neutral π-associated [2]catenanes

Chemistry - A European Journal

Volumn 4, Issue 4, 1998, Pages 608-620

  Hamilton, Darren G ^a   Davies, John E ^a   Prodi, Luca ^b   Sanders, Jeremy K M ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Catenanes; Donor acceptor systems; Photochemistry; Template synthesis

Indexed keywords

EID: 0031804095     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980416)4:4<608::AID-CHEM608>3.0.CO;2-C     Document Type: Article

References (94)

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3. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
4. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
5. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
6. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
7. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
8. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
9. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
10. For the first reports of the use of each of these approaches see a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098 (transition-metal coordination); b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404; Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399 (donor-acceptor interactions); c) C. A. Hunter. J. Am. Chem. Soc. 1992, 114, 5303-5311 (amide hydrogen-bonding). The latter approach has also been employed in extensive studies by two other groups; see d) F. Vögtle, S. Meier, R. Hoss. Angew. Chem. 1992, 104, 1628; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622; e) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
11. Comprehensive Supramolecular Chemistry, Vols. 1-11 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Elsevier, New York, 1996.
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13. No recognition is expressed between the molecular components before bipyridinium formation; see D. B. Amabilino, F. M. Raymo, J. F. Stoddart in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol. F. Vögtle), Elsevier, New York, 1996, pp. 85-130. The assembly of these systems may thus be viewed as trapping, by a molecular recognition process, of a reactive intermediate formed on the reaction pathway. The process may be astonishingly efficient, with yields of catenated products sometimes approaching 90%.
14. For examples of supramolecular systems where preexisting recognition characteristics lead to covalent bond formation by preassembly processes, see a) N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek Jr., J. Am. Chem. Soc. 1995, 117, 85-88; b) D. W. J. McCallien, J. K. M. Sanders, ibid. 1995, 117, 6611-6612. The transition metal templated catenane and knot syntheses developed by Sauvage also rely on preassembly; see C. O. Dietrich-Buchecker, J.-P. Sauvage, Bull. Soc. Chim. Fr. 1992, 129, 113-120.
15. For examples of supramolecular systems where preexisting recognition characteristics lead to covalent bond formation by preassembly processes, see a) N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek Jr., J. Am. Chem. Soc. 1995, 117, 85-88; b) D. W. J. McCallien, J. K. M. Sanders, ibid. 1995, 117, 6611-6612. The transition metal templated catenane and knot syntheses developed by Sauvage also rely on preassembly; see C. O. Dietrich-Buchecker, J.-P. Sauvage, Bull. Soc. Chim. Fr. 1992, 129, 113-120.
16. For examples of supramolecular systems where preexisting recognition characteristics lead to covalent bond formation by preassembly processes, see a) N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek Jr., J. Am. Chem. Soc. 1995, 117, 85-88; b) D. W. J. McCallien, J. K. M. Sanders, ibid. 1995, 117, 6611-6612. The transition metal templated catenane and knot syntheses developed by Sauvage also rely on preassembly; see C. O. Dietrich-Buchecker, J.-P. Sauvage, Bull. Soc. Chim. Fr. 1992, 129, 113-120.
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47. Some of the results discussed here have previously been reported in preliminary form; see D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898.
48. 1H NMR analyses of intermediates 2-5 are included in the Experimental Section.
49. D. Marquis, H. Greiving, J.-P. Desvergne, N. Lahrahar, P. Marsau, H. Hopf, H. Bouas-Laurent, Liebigs Ann./Recueil 1997, 97-106.
50. At ambient temperature and 5 mM concentration in DMF the mixture of 11 and 5 is appreciably more soluble than that of 10 and 5.
51. 13C NMR spectrum to be recorded.
52. An alternating internal-external stack of the intended type is formed between a 4,4′-bipyridinium derivative and the enlarged crown bis(1,5-dinaphtho)-44-crown-12: J.-Y. Ortholand, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1989, 101, 1402; Angew. Chem. Int. Ed. Engl. 1989, 28, 1394-1396. It is intriguing that although the solid-state structure of this complex provided at least part of the inspiration for the first π-associated catenane syntheses, all of these derivative syntheses were based around smaller crown components like 5.
53. An alternating internal-external stack of the intended type is formed between a 4,4′-bipyridinium derivative and the enlarged crown bis(1,5-dinaphtho)-44-crown-12: J.-Y. Ortholand, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1989, 101, 1402; Angew. Chem. Int. Ed. Engl. 1989, 28, 1394-1396. It is intriguing that although the solid-state structure of this complex provided at least part of the inspiration for the first π-associated catenane syntheses, all of these derivative syntheses were based around smaller crown components like 5.
54. Only two structures containing this diimide structural unit may be found in the CCDC database: a molecular cleft, see J. S. Nowick, P. Ballester, F. Ebmeyer, J. Rebek Jr., J. Am. Chem. Soc. 1990, 112, 8902-8906; and a complex of a diimide derived cyclophane, see ref. [11].
55. Electron donation into the naphthalenediimide LUMO does not have any measurable effect on the carbonyl bond lengths of the included substrate. Significant increases in these bond lengths are noted in the electronically equivalent parent dianhydride when reduced to its radical anion; see a) L. Born, G. Heywang, Z. Kristallogr. 1990, 190, 147-152; b) L. Born, G. Heywang, ibid. 1991, 197, 223-233.
56. Electron donation into the naphthalenediimide LUMO does not have any measurable effect on the carbonyl bond lengths of the included substrate. Significant increases in these bond lengths are noted in the electronically equivalent parent dianhydride when reduced to its radical anion; see a) L. Born, G. Heywang, Z. Kristallogr. 1990, 190, 147-152; b) L. Born, G. Heywang, ibid. 1991, 197, 223-233.
57. The structure of the 11·5 cocrystal serves to illustrate the distinct, and often misconceived, nature of donor-acceptor versus π-π interactions. Donor-acceptor interactions between complementary (that is, π-rich and π-poor) systems are characterised by substantial, symmetrical π-system overlap typically leading to linear columns of alternating donor and acceptor subunits. Cofacial interaction of electronically similar π systems leads to offset stacks, the herringbone arrays seen in the solid-state structures of many aromatic molecules; see C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534.
58. For an example of a chiral [2]catenate containing helical rings, see: C. Piguet, G. Bernardinelli, A. F. Williams, B. Bocquet, Angew. Chem. 1995, 107, 618; Angew. Chem. Int. Ed. Engl. 1995, 34, 582-584. Molecular knots are intrinsically chiral objects. The enantiomers of such a system have recently been resolved; see G. Rapenne, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 10932-10933.
59. For an example of a chiral [2]catenate containing helical rings, see: C. Piguet, G. Bernardinelli, A. F. Williams, B. Bocquet, Angew. Chem. 1995, 107, 618; Angew. Chem. Int. Ed. Engl. 1995, 34, 582-584. Molecular knots are intrinsically chiral objects. The enantiomers of such a system have recently been resolved; see G. Rapenne, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 10932-10933.
60. For an example of a chiral [2]catenate containing helical rings, see: C. Piguet, G. Bernardinelli, A. F. Williams, B. Bocquet, Angew. Chem. 1995, 107, 618; Angew. Chem. Int. Ed. Engl. 1995, 34, 582-584. Molecular knots are intrinsically chiral objects. The enantiomers of such a system have recently been resolved; see G. Rapenne, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 10932-10933.
61. See ref. [16a]. The relationship of host cavity size and twist angle for some related cyclophanes has been discussed; see H.-E. Hogberg, O. Wennerström, Acta. Chem. Scand. 1982, B 36, 661-667.
62. 6]DMSO solvent molecules.
63. D. G. Hamilton, N. Feeder, L. Prodi, S. J. Teat, W. Clegg, J. K. M. Sanders, J. Am. Chem. Soc. 1998, 120, 1096-1097.
64. 3.
65. 2 axis may be drawn perpendicular to the plane of the donor-acceptor pair of catenane 12, explaining the magnetic equivalence of the aromatic protons on each side of each component.
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67. 2 units in the polyether chain.
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80. 3, has been used to assemble a [2]catenane from two identical platinum-bridged macrocyles; see M. Fujita, F. Ibukuro, K. Yamaguchi, K. Ogura, J. Am. Chem. Soc. 1995, 117, 4175-4176.
81. 3, has been used to assemble a [2]catenane from two identical platinum-bridged macrocyles; see M. Fujita, F. Ibukuro, K. Yamaguchi, K. Ogura, J. Am. Chem. Soc. 1995, 117, 4175-4176.
82. 3, has been used to assemble a [2]catenane from two identical platinum-bridged macrocyles; see M. Fujita, F. Ibukuro, K. Yamaguchi, K. Ogura, J. Am. Chem. Soc. 1995, 117, 4175-4176.
83. 3, has been used to assemble a [2]catenane from two identical platinum-bridged macrocyles; see M. Fujita, F. Ibukuro, K. Yamaguchi, K. Ogura, J. Am. Chem. Soc. 1995, 117, 4175-4176.
84. 3, has been used to assemble a [2]catenane from two identical platinum-bridged macrocyles; see M. Fujita, F. Ibukuro, K. Yamaguchi, K. Ogura, J. Am. Chem. Soc. 1995, 117, 4175-4176.
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93. Note added in proof (6th March 1998): Increasing the ratio of bisacetylene 10 to crown 5 to 20:1 increases the isolated yield (based on crown 5) of [2]catenane 12 to 62%: Q. Zhang, D. G. Hamilton, J. K. M. Sanders, unpublished results.
94. Reference added in proof (6th March 1998): For the use of these and related building blocks in a reversible, thermodynamically controlled [2]catenane synthesis see: A. C. Try, M. M. Harding, D. G. Hamilton, J. K. M. Sanders, Chem. Commun. 1998, 723-724.