Formation of supramolecular polymers from homoditopic molecules containing secondary ammonium ions and crown ether moieties

Angewandte Chemie - International Edition

Volumn 38, Issue 1-2, 1999, Pages 143-147

  Yamaguchi, Nori ^a   Gibson, Harry W ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Crown compounds; Homoditopic molecules; Noncovalent interactions; Self organization; Supramolecular chemistry

Indexed keywords

AMMONIA; CROWN ETHER; POLYMER;

ARTICLE; MATERIAL STATE; MOLECULAR INTERACTION; POLYMERIZATION; SYNTHESIS;

EID: 0033555197     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990115)38:1/2<143::aid-anie143>3.0.co;2-y     Document Type: Article

References (35)

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15. 1H NMR spectroscopy.
16. The NOESY spectra of 1:1 stoichiometric solutions of 3a and 7 could not be recorded at concentrations greater than 1.0M because of overloading of the analogue to digital converter.
17. The average molecular weight of 9 was calculated on the assumption that the cyclic oligomers such as 2:2 and 3:3 complexes were absent. It is noteworthy that linear polymerization is highly favored over cyclization at high solution concentrations (for example, 1.0M). For reviews on cyclization versus linear polymerization, see a) G. Odian, Principles of Polymerization, 3rd ed., Wiley, New York, 1991, p. 73;
18. n of 9 was calculated.
19. A mixture of acetone/chloroform (1/1) was added to a flask containing 3a (1.1233g) and 7 (0.8568 g) until complete dissolution occurred. The solution was slowly concentrated and vacuum dried to afford 9, which was then diluted with acetone/chloroform (1/1) to 0.50 mL.
20. Similar effects have been observed in a supramolecule assembled from a heteroditopic precursor. See N. Yamaguchi, D. S. Nagvekar, H. W. Gibson, Angew. Chem. 1998, 110, 2518-2520; Angew. Chem. Int. Ed. 1998, 37, 2361-2364.
21. Similar effects have been observed in a supramolecule assembled from a heteroditopic precursor. See N. Yamaguchi, D. S. Nagvekar, H. W. Gibson, Angew. Chem. 1998, 110, 2518-2520; Angew. Chem. Int. Ed. 1998, 37, 2361-2364.
22. 3]chloroform (1/1) did not show extra sets of signals from slow exchange or changes in the chemical shifts from fast exchange. The m-phenylene linkage prevents pseudorotaxane formation in solution.
23. The solutions were frozen at -93 C with an acetone-ethanol/liquid nitrogen bath and the solvents were removed under high vacuum to give yellow-orange solids.
24. 1 and the DSC thermograms were recorded.
25. n values of the freeze-dried (-93 C) samples were estimated by simple integration of relevant signals of the spectra recorded at -40 C.
26. A similar dimeric cyclic species has recently heen reported: P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347; Angew. Chem. Int. Ed. 1998, 37, 1294-1297.
27. A similar dimeric cyclic species has recently heen reported: P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347; Angew. Chem. Int. Ed. 1998, 37, 1294-1297.
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31. [2f h] For a review on fiber theory, see H. L. Needles, Handbook of Textile Fibers, Dyes, and Finishes, Garland STPM, New York, 1981, pp. 1-27.
32. [2f h] For a review on fiber theory, see H. L. Needles, Handbook of Textile Fibers, Dyes, and Finishes, Garland STPM, New York, 1981, pp. 1-27.
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