Michelle L. Renak, G. P. Bartholomew, Shujun Wang
Aug 13, 1999
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Journal
Journal of the American Chemical Society
Abstract
A series of fluorinated distyrylbenzene (DSB) derivatives were synthesized and studied in order to probe the effect of fluorine substitution on molecular properties and on the arrangement of molecules in the solid state. Reaction of 1,4-diiodobenzene with 4-fluorostyrene or pentafluorostyrene in the presence of Pd(OAc)2 gives trans-trans-bis(4-fluorostyryl)benzene (2Ft) and trans-trans-1,4-bis(pentafluorostyryl)benzene (10Ft), respectively. Bis(2,5-difluorostyryl)benzene (4Ft) was prepared by the reaction of 2,5-difluorobenzaldehyde with p-xylylenebis-(triphenylphosphonium bromide) in the presence of LiOEt in EtOH. Coupling of 1,4-dibromo-2,5-difluorobenzene with styrene, 4-fluorostyrene, or pentafluorostyrene using Pd(OAc)2 gives 1,4-bis(styryl)-2,5-difluorobenzene (2Fc), 1,4-bis(4-fluorostyryl)-2,5-difluorobenzene (2Fc2Ft), and 1,4-bis(pentafluorostyryl)-2,5-difluorobenzene (2Fc10Ft), respectively. Absorption spectroscopy shows that DSB, 2Ft, 2Fc, 2Fc2Ft, 4Ft, 10Ft, and 2Fc10Ft have a λmax at approximat...