Organic glass-forming materials: 1,3,5-tris(naphthyl)benzene derivatives.
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.
Bonvallet
Paul A
PA
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Breitkreuz
Caroline J
CJ
Kim
Yong Seol
YS
Todd
Eric M
EM
Traynor
Katherine
K
Fry
Charles G
CG
Ediger
M D
MD
McMahon
Robert J
RJ