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5-Bromo-2-iodopyrimidine
Abstract
The title compound, C4H2BrIN2, is a useful intermediate for various sytheses. The complete molecule is located on a crystallographic mirror plane.
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A simple synthesis of the novel 5-bromo-2-iodopyrimidine is described and examples are provided of the use of the compound in selective palladium-catalysed cross-coupling reactions with a wide range of arylboronic acids and alkynylzincs to give the efficient syntheses of many substituted pyrimidine compounds.
Palladium-catalyzed Stille and Sonogashira coupling reactions were sequentially applied for constructing novel pyrimidine-containing linear molecules. The chemoselectivity of 5-bromo-2-iodopyrimidine (1) towards Pd-catalyzed coupling reaction serves as a tool for the successful control of the arrangement of dipolar pyrimidine moieties inside the conjugated backbone. The influence of the arrangement of dipolar pyrimidine in the linear backbone on their absorption and photoluminescence are not stupendous. Thermogravimetric analysis (TGA) indicate that all linear molecules in this study exhibit high thermal stability.
[reaction: see text] Conjugated oligomers with an alternating phenylene-pyrimidine structure have been synthesized by the successive Suzuki coupling reaction starting from 2-bromo-5-iodopyrimidine. The photoluminescence properties and quasi-reversible redox behavior of these oligomers make them applicable as an active material for a light-emitting device. Blue light-emitting electroluminescent devices with an external quantum efficiency up to 1.8% have been fabricated.
The synthesis of a novel, photopolymerisable liquid crystal (reactive mesogen) with a high mobility of electrons in the smectic C phase at room temperature is reported for the first time as a potential charge transport layer for OLEDs.