Hexagonal packing of oligo(m-phenylene ethynylene)s in the solid state: Helical nanotubules [15]

Journal of the American Chemical Society

Volumn 122, Issue 25, 2000, Pages 6134-6135

  Mio, Matthew J ^a   Prince, Ryan B ^a,c   Moore, Jeffrey S ^a   Kuebel, Christian ^b   Martin, David C ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c 3M COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE DERIVATIVE; OLIGO(PHENYLENE ETHYNYLENE); UNCLASSIFIED DRUG;

ANALYTIC METHOD; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DRUG SYNTHESIS; LETTER; PROTEIN MODIFICATION; SOLID STATE; X RAY DIFFRACTION;

EID: 0034725404     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000380o     Document Type: Letter

References (30)

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15. Prince, R. B. Phenylene Ethynylene Foldamers: Cooperative Conformational Transition, Twist Sense Bias, Molecular Recognition Properties, and Solid-State Organization. Ph.D. Thesis, University of Illinois, Urbana, IL, January 2000.
16. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 2643-2644.
17. 1H NMR and mass spectrometry (FAB or MALDI). Purity was assessed by HPLC and GPC. As in our previous studies with these oligomers, the UV-vis absorption spectra and fluorescence emission spectra were solvent-dependent for all molecules except for sequences shorter than 10 units. Such oligomers are too short to solvophobically collapse into stable helical conformations.
18. Samples were stable at ambient temperature and pressure for at least 4 months. No change in X-ray patterns was observed after evacuation. Thus, we rule out a lyotropic phase.
19. 16 However, in these cases, very little internal space remains. In the case of series 2, an internal tube diameter of approximately 7 A° is generated.
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23. While the hydrogen-substituted octadecamer 1 (n = 18) has yet to be imaged due to the thickness of crystals, selected area electron diffraction (SAED) patterns of the methyl-substituted analogue 2 (n = 18) support the conclusion of hexagonal packing with lattice spacings of ̃30 Å. Lattice fringes of different crystallographic zones, including the ̃26 Å (100) and the ̃15.5 Å (110) spacings, were observed in high-resolution transmission electron microscopy (HR-TEM) and are consistent with the proposed structure.
24. Rigorous steps were taken to ensure these signals were not due to a sample impurity or instrumental artifacts.
25. The observed hexagonal packing is most likely metastable since those oligomers of 2 prepared from the melt form lamellar phases.
26. (a) Mindyuk, O. Y.; Stetzer, M. R.; Heiney, P. A.; Nelson, J. C.; Moore, J. S. Adv. Mater. 1998, 10, 1363-1366.
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30. (c) Prince, R. B.; Brunsveld, L.; Meijer, E. W.; Moore, J. S. Angew. Chem., Int. Ed. 2000, 39, 228-230.