Cooperative polar ordering of acentric guest molecules in topologically controlled host frameworks

Chemistry of Materials

Volumn 12, Issue 6, 2000, Pages 1501-1504

  Swift, Jennifer A ^a,b   Ward, Michael D ^a  

^a University of Minnesota   (United States)

^b GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 IODONAPHTHALENE; 1 NAPHTHONITRILE; 1 NITRONAPHTHALANE; 4,4' BIPHENYLDISULFONIC ACID; GUANIDINE; NAPHTHALENE DERIVATIVE; NITRO 2 XYLENE; ORTHO XYLENE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; DIPOLE; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY;

EID: 0033804102     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm000026p     Document Type: Article

References (31)

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11. Evans, C. C.; Sukarto, L.; Ward, M. D. J. Am. Chem. Soc. 1999, 121, 320.
12. Swift, J. A.; Reynolds, A. M.; Ward, M. D. Chem. Mater. 1998, 10, 4159.
13. w = 0.047/0.107. Presently, we have not observed any polymorphs of these materials.
14. The values for the dihedral angle φ are as follows: I, 34.4°; II, 33.9°; III, 35.2°; and IV, 35.0°.
15. This is described as a "pseudo" body-centered orthorhombic motif because the lattice representations in Figure 2 actually have dimensions corresponding to a/2, b, c due to the crystallographic inequivalence of adjacent guests in the a-axis channels.
16. 1 space group because the data supported an unequal population of the two guest orientations; however, the disorder closely approaches that expected for a centrosymmetric solution.
17. Marder, S. R.; Perry, J. W.; Schaefer, W. P. Science 1989, 245, 626.
18. Whitesell, J. K.; Davis, R. E.; Saunders, L. L.; Wilson, R. J.; Feagins, J. P. J. Am. Chem. Soc. 1991, 113, 3267.
19. Reported dipole moments: μ(NX) = 4.82: Ivanov, M. G.; Zhuravlev, E. Z.; Dergunov, Yu. I.; Elizarova, T. P. J. Gen. Chem. USSR 1990, 60, 1078. μ(NN) = 4.00: Rampolla, R. W.; Smyth, C. P. J. Am. Chem. Soc. 1958, 80, 1057. μ(IN) = 3.99: Le Fevre, R. J.; Sundaram, W. A. J. Chem. Soc. 1962, 4756. μ(CN) = 1.44: Jain, S. R.; Walker, S. J. Phys. Chem. 1971, 75, 2942.
20. Reported dipole moments: μ(NX) = 4.82: Ivanov, M. G.; Zhuravlev, E. Z.; Dergunov, Yu. I.; Elizarova, T. P. J. Gen. Chem. USSR 1990, 60, 1078. μ(NN) = 4.00: Rampolla, R. W.; Smyth, C. P. J. Am. Chem. Soc. 1958, 80, 1057. μ(IN) = 3.99: Le Fevre, R. J.; Sundaram, W. A. J. Chem. Soc. 1962, 4756. μ(CN) = 1.44: Jain, S. R.; Walker, S. J. Phys. Chem. 1971, 75, 2942.
21. Reported dipole moments: μ(NX) = 4.82: Ivanov, M. G.; Zhuravlev, E. Z.; Dergunov, Yu. I.; Elizarova, T. P. J. Gen. Chem. USSR 1990, 60, 1078. μ(NN) = 4.00: Rampolla, R. W.; Smyth, C. P. J. Am. Chem. Soc. 1958, 80, 1057. μ(IN) = 3.99: Le Fevre, R. J.; Sundaram, W. A. J. Chem. Soc. 1962, 4756. μ(CN) = 1.44: Jain, S. R.; Walker, S. J. Phys. Chem. 1971, 75, 2942.
22. Reported dipole moments: μ(NX) = 4.82: Ivanov, M. G.; Zhuravlev, E. Z.; Dergunov, Yu. I.; Elizarova, T. P. J. Gen. Chem. USSR 1990, 60, 1078. μ(NN) = 4.00: Rampolla, R. W.; Smyth, C. P. J. Am. Chem. Soc. 1958, 80, 1057. μ(IN) = 3.99: Le Fevre, R. J.; Sundaram, W. A. J. Chem. Soc. 1962, 4756. μ(CN) = 1.44: Jain, S. R.; Walker, S. J. Phys. Chem. 1971, 75, 2942.
23. The crystal structures reveal N-H⋯heteroatom distances that are larger than conventionally accepted values for hydrogen bond distances, assuming ideal positions for the hydrogen atoms. [See: Taylor, R.; Kennard, O. Acc. Chem. Res. 1984, 17, 320; Etter, M. C. Acc. Chem. Res. 1990, 23, 120.]
24. The crystal structures reveal N-H⋯heteroatom distances that are larger than conventionally accepted values for hydrogen bond distances, assuming ideal positions for the hydrogen atoms. [See: Taylor, R.; Kennard, O. Acc. Chem. Res. 1984, 17, 320; Etter, M. C. Acc. Chem. Res. 1990, 23, 120.]
25. (a) Tiller, W. A The Science of Crystallization: Microscopic Interfacial Phenomena; Cambridge University Press: Cambridge, April 1991.
26. (b) Tiller, W. A. The Science of Crystallization: Macroscopic Phenomena and Defect Generation; Cambridge University Press: Cambridge, March 1992.
27. Real-time, in-situ atomic force microscopy performed in our laboratory has demonstrated that the growth of molecular crystals typically proceeds via layer-by-layer growth. (a) Carter, P. W.; Hillier, A. C.; Ward, M. D. J. Am. Chem. Soc. 1994, 116, 944-953. (b) Mao, G. Z.; Lobo, L.; Scaringe, R.; Ward, M. D. Chem. Mater. 1997, 9, 773. Compounds I-IV each exhibit a blocklike morphology, signifying roughly equal growth rates in the three principal lattice directions. We surmise this is a consequence of the favorable growth parallel to the GS sheet because of hydrogen bonding, and growth normal to the sheet promoted by the protruding pillars. (Crystals with the brick architecture as in I-IV cannot terminate with a molecularly smooth surface.) AFM investigations of the crystallization of these inclusion compounds are in progress.
28. Real-time, in-situ atomic force microscopy performed in our laboratory has demonstrated that the growth of molecular crystals typically proceeds via layer-by-layer growth. (a) Carter, P. W.; Hillier, A. C.; Ward, M. D. J. Am. Chem. Soc. 1994, 116, 944-953. (b) Mao, G. Z.; Lobo, L.; Scaringe, R.; Ward, M. D. Chem. Mater. 1997, 9, 773. Compounds I-IV each exhibit a blocklike morphology, signifying roughly equal growth rates in the three principal lattice directions. We surmise this is a consequence of the favorable growth parallel to the GS sheet because of hydrogen bonding, and growth normal to the sheet promoted by the protruding pillars. (Crystals with the brick architecture as in I-IV cannot terminate with a molecularly smooth surface.) AFM investigations of the crystallization of these inclusion compounds are in progress.
29. Interestingly, the dipole motifs in C and D closely resemble that in "spin frustrated" triangular Ising spin lattices, in which optimal antiferromagnetic alignment of neighboring spins is not achievable, making conditions for a ferromagnetic state more favorable. [Wannier, G. H. Phys. Rev. 1950, 79, 357. Bruinsma, R.; Aeppli, G. Phys. Rev. B 1984, 29, 2644.] Similarly, "dipole frustration" in motifs C and D would make motif A more favorable if dipole-dipole terms contribute to guest ordering.
30. Interestingly, the dipole motifs in C and D closely resemble that in "spin frustrated" triangular Ising spin lattices, in which optimal antiferromagnetic alignment of neighboring spins is not achievable, making conditions for a ferromagnetic state more favorable. [Wannier, G. H. Phys. Rev. 1950, 79, 357. Bruinsma, R.; Aeppli, G. Phys. Rev. B 1984, 29, 2644.] Similarly, "dipole frustration" in motifs C and D would make motif A more favorable if dipole-dipole terms contribute to guest ordering.
31. Zyss, J.; Oudar, J. L. Phys. Rev. A 1982, 26, 2028.