Synthesis and characterization of organic materials with conveniently accessible supercooled liquid and glassy phases: Isomeric 1,3,5-tris(naphthyl)benzenes

Journal of Physical Chemistry

Volumn 100, Issue 3, 1996, Pages 1081-1090

  Whitaker, Craig M ^a   McMahon, Robert J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748544001     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9529329     Document Type: Article

References (68)

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59. In principle, the symmetry-equivalent 1-naphthyl groups in 1b can rotate in either of two nonequivalent directions: toward the syn 1-naphthyl group or toward the anti 1-naphthyl group. The computed barriers for these processes, 13 kcal/mol, are indistinguishable within the accuracy of our calculations.
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62. 13C NMR resonances in 1 and 2, we obtained four separate values for the aryl-1-naphthyl rotational barriers. In each case, these four values were averaged to give the quoted barrier of 12.0 kcal/mol. The individual values all lie within the range 12.0 ± 0.4 kcal/mol.
63. In principle, the symmetry equivalent 1-naphthyl groups in 2a and 2c can rotate in either of two nonequivalent directions: toward the other 1-naphthyl group or toward the 2-naphthyl group. The computed barriers for these processes, 14 kcal/mol, are indistinguishable within the accuracy of our calculations.
64. In principle, the 1-naphthyl groups in 2b can rotate in either of two nonequivalent directions: toward the other 1-naphthyl group or toward the 2-naphthyl group. The computed barriers for these processes, 14 kcal/ mol, are indistinguishable within the accuracy of our calculations. Similarly, the 2-naphthyl group in 2b can rotate in either of two nonequivalent directions: toward the syn 1-naphthyl group or toward the anti 1-naphthyl group. The computed barriers for these processes, 2 kcal/mol, are indistinguishable within the accuracy of our calculations.
65. The limited solubility of tris(naphthyl)benzenes 1 and 2 in THF at temperatures below 193 K precluded NMR studies at lower temperatures.
66. 1H NMR spectroscopy would not have been diagnostic.
67. See unpublished data cited in refs 7 and 8.
68. g from the midpoint along the curve between the two tangents to the base lines or from the extrapolated onset of the glass transition (see Figure 7).