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Volumn 45, Issue 26, 2006, Pages 4281-4286

Dynamic covalently bonded rotaxanes cross-linked by imine bonds between the axle and ring: Inverse temperature dependence of subunit mobility

Author keywords

Entropy; Imines; Molecular dynamics; Rotaxanes; Template synthesis

Indexed keywords

CROSSLINKING; NITROGEN COMPOUNDS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33746274988     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600750     Document Type: Article
Times cited : (67)

References (48)
  • 1
    • 0003542983 scopus 로고    scopus 로고
    • (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim
    • a) Molecular Catenanes, Rotaxanes, and Knots (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999;
    • (1999) Molecular Catenanes, Rotaxanes, and Knots
  • 3
    • 0034596923 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3348-3391
  • 4
    • 0034852567 scopus 로고    scopus 로고
    • c) Molecular Machines Special Issue, Acc. Chem. Res. 2001, 34, 409-522;
    • (2001) Acc. Chem. Res. , vol.34 , Issue.MOLECULAR MACHINES SPEC. ISSUE , pp. 409-522
  • 5
    • 0004240038 scopus 로고    scopus 로고
    • (Eds.: B. L. Feringa), Wiley-VCH, Weinheim
    • d) Molecular Switches (Eds.: B. L. Feringa), Wiley-VCH, Weinheim, 2001;
    • (2001) Molecular Switches
  • 7
    • 0012317549 scopus 로고    scopus 로고
    • (Eds.: V. Balzani, M. Venturi, A. Credi), Wiley-VCH, Weinheim
    • f) Molecular Devices and Machines (Eds.: V. Balzani, M. Venturi, A. Credi), Wiley-VCH, Weinheim, 2003;
    • (2003) Molecular Devices and Machines
  • 8
    • 84867530446 scopus 로고    scopus 로고
    • (Eds.: T. Schrader, A. D. Hamilton), Wiley-VCH, Weinheim, chap. 7
    • g) E. R. Kay, D. A. Leigh in Functional Synthetic Receptors (Eds.: T. Schrader, A. D. Hamilton), Wiley-VCH, Weinheim, 2005, chap. 7.
    • (2005) Functional Synthetic Receptors
    • Kay, E.R.1    Leigh, D.A.2
  • 16
    • 0037192455 scopus 로고    scopus 로고
    • g) J.-M. Lehn, Science 2002, 295, 2400-2403.
    • (2002) Science , vol.295 , pp. 2400-2403
    • Lehn, J.-M.1
  • 18
  • 19
    • 0004043430 scopus 로고
    • (Ed.: S. Patai), Wiley, London, chap. 7
    • c) The Chemistry of the Amino Group (Ed.: S. Patai), Wiley, London, 1968, chap. 7;
    • (1968) The Chemistry of the Amino Group
  • 21
    • 0000234038 scopus 로고
    • Imine-bond formation has been utilized to construct individual axle or ring components in interlocked compounds, such as rotaxanes and a Borromean ring, see: a) J. Y. Sze, H. W. Gibson, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 1992, 33, 331-332;
    • (1992) Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. , vol.33 , pp. 331-332
    • Sze, J.Y.1    Gibson, H.W.2
  • 25
    • 0035906693 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1870-1875;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1870-1875
  • 29
    • 34848817399 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 1217-1221;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1217-1221
  • 31
    • 4544325562 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3292-3300;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3292-3300
  • 37
    • 0040979358 scopus 로고
    • For other methods for the preparation of interlocked compounds through covalent-bond formation, see: a) G. Schill, A. Lùttringhaus, Angew. Chem. 1964, 76, 567-568;
    • (1964) Angew. Chem. , vol.76 , pp. 567-568
    • Schill, G.1    Lùttringhaus, A.2
  • 44
    • 33746290946 scopus 로고    scopus 로고
    • 2) = 0.244 (all data). Estimated standard deviations for bond lengths and angles are 0.009-0.02 Å and 0.6-1.0° for non-hydrogen atoms. CCDC-252150 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
  • 45
    • 33746297566 scopus 로고    scopus 로고
    • See the Supporting information
    • See the Supporting information.
  • 46
    • 33746297827 scopus 로고    scopus 로고
    • note
    • 1H NMR signals, except for those of the end groups, broadened under the hydrolytic conditions, thus suggesting that the hydrolysis that generates 9e and 2e might proceed to some extent; however, the expected CHO signals were not clearly discernible and the propargyl methylene protons on the macrocycle remained nonequivalent to each other. Thus, the equilibration among 1e, 9e, and 2e seems to be heavily in favor of 1e under the hydrolytic conditions, and as a result the preorganization of the macrocycle favors imine formation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.