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  • Title: Organic glass-forming materials: 1,3,5-tris(naphthyl)benzene derivatives.
    Author: Bonvallet PA, Breitkreuz CJ, Kim YS, Todd EM, Traynor K, Fry CG, Ediger MD, McMahon RJ.
    Journal: J Org Chem; 2007 Dec 21; 72(26):10051-7. PubMed ID: 18020366.
    Abstract:
    The organic glass-forming materials 1,3-bis(1-naphthyl)-5-(2-naphthyl)benzene (2) and its partially deuterated analogue, 1,3-bis(1-naphthyl-d(7))-5-(2-naphthyl)benzene (2-d(14)), have been synthesized on a gram scale using Suzuki coupling reactions. Detailed spectroscopic studies afford complete NMR assignments (1H, 2H, 13C) for both compounds. Modest energy barriers for the interconversion of atropisomers (ca. 15 kcal/mol) result in a propensity for these materials to form supercooled liquids and glasses, rather than undergoing crystallization. The preparation of these materials enables detailed studies of physical properties of organic glasses and molecular diffusion in condensed phases.
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