A Cucurbituril-Based Gyroscane: A New Supramolecular Form
Anthony I. Day Dr.
School of Chemistry, University College University of New South Wales Australian Defence Force Academy Canberra, ACT 2600 (Australia) Fax: (+61) 2-6268-8002
Search for more papers by this authorRodney J. Blanch Dr.
School of Chemistry, University College University of New South Wales Australian Defence Force Academy Canberra, ACT 2600 (Australia) Fax: (+61) 2-6268-8002
Search for more papers by this authorAlan P. Arnold Dr.
School of Chemistry, University College University of New South Wales Australian Defence Force Academy Canberra, ACT 2600 (Australia) Fax: (+61) 2-6268-8002
Search for more papers by this authorSusan Lorenzo
School of Chemistry University of New South Wales Sydney NSW 2052 (Australia)
Search for more papers by this authorGareth R. Lewis Dr.
School of Chemistry University of Nottingham Nottingham NG7 2RD (UK)
Search for more papers by this authorIan Dance Prof. Dr.
School of Chemistry University of New South Wales Sydney NSW 2052 (Australia)
Search for more papers by this authorAnthony I. Day Dr.
School of Chemistry, University College University of New South Wales Australian Defence Force Academy Canberra, ACT 2600 (Australia) Fax: (+61) 2-6268-8002
Search for more papers by this authorRodney J. Blanch Dr.
School of Chemistry, University College University of New South Wales Australian Defence Force Academy Canberra, ACT 2600 (Australia) Fax: (+61) 2-6268-8002
Search for more papers by this authorAlan P. Arnold Dr.
School of Chemistry, University College University of New South Wales Australian Defence Force Academy Canberra, ACT 2600 (Australia) Fax: (+61) 2-6268-8002
Search for more papers by this authorSusan Lorenzo
School of Chemistry University of New South Wales Sydney NSW 2052 (Australia)
Search for more papers by this authorGareth R. Lewis Dr.
School of Chemistry University of Nottingham Nottingham NG7 2RD (UK)
Search for more papers by this authorIan Dance Prof. Dr.
School of Chemistry University of New South Wales Sydney NSW 2052 (Australia)
Search for more papers by this authorThis research was supported by the Australian Research Council and the University of New South Wales. G.R.L. acknowledges the award of a Royal Society Fellowship tenable in Australia.
Graphical Abstract
Konzentrische rotierende und präzedierende Makrocyclen: Einer Kristallstrukturanalyse des Einschlusskomplexes von Cucurbit[5]uril in Cucurbit[10]uril zufolge sind die beiden Makrocyclen konzentrisch, aber nicht koaxial, und ganz im Innern befindet sich ein Chloridion (siehe Bild). Beide Ringe bewegen sich in Lösung relativ zueinander, wie NMR-spektroskopisch gezeigt wurde. Die Rotation und Präzession des inneren Rings im äußeren lässt das Bild eines „molekularen Gyroskops“ zu.
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References
- 1 W. A. Freeman, W. L. Mock, N. Y. Shih, J. Am. Chem. Soc. 1981, 103, 7367–7368.
- 2 P. Cintas, J. Inclusion Phenom. 1994, 17, 205–220.
- 3 W. L. Mock, Top. Curr. Chem. 1995, 175, 1–24.
- 4 W. L. Mock in Comprehensive Supramolecular Chemistry, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle), Pergamon, Oxford, 1996, pp. 477–493.
- 5
- 5a A. I. Day, A. P. Arnold, R. J. Blanch Unisearch Limited, Australia, PCT Int. Appl. 2000, WO2000-2000AU412 20000505, 112 (Priority: AU 99-232 19990507);
- 5b A. Day, A. P. Arnold, R. J. Blanch, B. Snushall, J. Org. Chem. 2001, 66, 8094–8100.
- 6 J. Kim, I.-S. Jung, S.-Y. Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2000, 122, 540–541.
- 7 M. El Haouaj, M. Luhmer, Y. H. Ko, K. Kim, K. Bartik, J. Chem. Soc. Perkin Trans. 2 2001, 5, 804–807.
- 8 W. A. Freeman, Acta Crystallogr. Sect. B 1984, 40, 382–387.
- 9
- 9a Y.-M. Jeon, J. Kim, D. Whang, K. Kim, J. Am. Chem. Soc. 1996, 118, 9790–9791;
- 9b
D. Whang, J. Heo, J. H. Park, K. Kim, Angew. Chem. 1998, 110, 83–85;
10.1002/(SICI)1521-3757(19980116)110:1/2<83::AID-ANGE83>3.0.CO;2-S Google ScholarAngew. Chem. Int. Ed. 1998, 37, 78–80;10.1002/(SICI)1521-3773(19980202)37:1/2<78::AID-ANIE78>3.0.CO;2-9 CAS Web of Science® Google Scholar
- 9c
J. Heo, S.-Y. Kim, D. Whang, K. Kim, Angew. Chem. 1999, 111, 675–678;
10.1002/(SICI)1521-3757(19990301)111:5<675::AID-ANGE675>3.0.CO;2-# Google ScholarAngew. Chem. Int. Ed. 1999, 38, 641–643.10.1002/(SICI)1521-3773(19990301)38:5<641::AID-ANIE641>3.0.CO;2-O CAS PubMed Web of Science® Google Scholar
- 10 D. A. Dantz, C. Meschke, H.-J. Buschmann, E. Schollmeyer, Supramol. Chem. 1998, 9, 79–83.
- 11 V. P. Fedin, A. V. Virovets, M. N. Sokolov, D. N. Dybtsev, O. A. Gerasko, W. Clegg, Inorg. Chem. 2000, 39, 2227–2230.
- 12 D. Tuncel, J. H. G. Steinke, Chem. Commun. 2001, 253–254.
- 13
- 13a
K. Kim, in Transition metals in supramolecular chemistry ( ), Wiley, New York, 1999, pp. 371–402;
10.1002/9780470511510.ch8 Google Scholar
- 13b
S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672–675;
Angew. Chem. Int. Ed. 1999, 38, 638–641;
10.1002/(SICI)1521-3773(19990301)38:5<637::AID-ANIE637>3.0.CO;2-4 CAS Web of Science® Google Scholar
- 13c J. Heo, S.-Y. Kim, S.-G. Roh, K.-M. Park, G.-J. Park, D. Whang, K. Kim, Mol. Cryst. Liq. Cryst. 2000, 342, 29–38;
- 13d
E. Lee, J. Heo, K. Kim, Angew. Chem. 2000, 112, 2811–2813;
Angew. Chem. Int. Ed. 2000, 39, 2699–2701;
10.1002/1521-3773(20000804)39:15<2699::AID-ANIE2699>3.0.CO;2-Z CAS PubMed Web of Science® Google Scholar
- 13e
E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413–416;
Angew. Chem. Int. Ed. 2001, 40, 399–402.
10.1002/1521-3773(20010119)40:2<399::AID-ANIE399>3.0.CO;2-W CAS PubMed Web of Science® Google Scholar
- 14
S.-Y. Kim, I.-S. Jung, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 2177–2179;
Angew. Chem. Int. Ed. 2001, 40, 2119–2121.
10.1002/1521-3773(20010601)40:11<2119::AID-ANIE2119>3.0.CO;2-4 CAS PubMed Web of Science® Google Scholar
- 15 S. Lorenzo, A. Day, D. Craig, R. Blanch, A. Arnold, I. Dance, CrystEngComm 2001, 49.
- 16 R. J. Blanch, A. J. Sleeman, T. J. White, A. P. Arnold, A. I. Day, Nano Lett. 2001, in press, web release date: December 6, 2001.
- 17
Crystal data: colorless parallelepipeds 0.25×0.15×0.15 mm, (C60H60N40O20)(C30H34N20O12Cl)⋅23.75 H2O⋅10 HCl, Mr=3321.14, triclinic, space group P
, a=20.047(4), b=20.064(4), c=23.978(5) Å, α=67.44(3), β=84.93(3), γ=66.36(3)°, V=8134(3) Å3, Z=2, ρcalcd=1.662 g cm−3, T=293 K, Bruker-AXS SMART CCD diffractometer, MoKα (λ=0.71073 Å), μ=0.755 cm−1, 59 909 reflections measured for θ≤23°, R1 (I>2σ(I))=0.1255. Higher symmetry was excluded with the program PLATON, but it is possible that some twinning is present in the crystal investigated. A number (15.75) of the water molecules in the lattice are ill-defined, but the gyroscane complex is well-defined. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-169807. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: [email protected]).
- 18a The Cl− ion is 0.03 Å from the equatorial plane of Q5, and 0.04 Å from the equatorial plane of Q10;
- 18b the relevant hydrogen atoms have not been located. It is not known whether the central species is Cl−, HCl, or HClH+. Around each Q5 portal water site there are seven O atoms (five from Q5 at about 2.7 Å and two from Q10 at about 3.4 Å) that are geometrically consistent with it possessing disordered hydrogen bonding of OH2 or OH3+. The internal assembly could be [H3O⋅H⋅Cl⋅H⋅OH3]3+.
- 19 H. W. Kroto, Nature 1992, 359, 670–671.
- 20
- 20a
V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484–3530;
10.1002/1521-3757(20001002)112:19<3484::AID-ANGE3484>3.0.CO;2-O Google ScholarAngew. Chem. Int. Ed. 2000, 39, 3348–3391;10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 20b Special Issue: Acc. Chem. Res. 2001, 34(6), is devoted to molecular machines and contains several excellent reviews in this area.
- 21 J. Cumings, A. Zettl, Science 2000, 289, 602–604.
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