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First examples of functionalized triphenylene discotic dimers: molecular engineering of advanced materials
Abstract:A series of novel functionalized triphenylene discotic dimers was synthesized starting from 2-hydroxy-3,6,7,10,11-pentaalkoxytriphenylene. Nitration of monohydroxypentaalkoxytriphenylene gave the mononitromonohydroxypentaalkoxytriphenylene which was alkylated with 2-bromoethanol. The resulting alcohol was coupled with various diacids. These compounds are unique in that they possess an electron withdrawing group (and consequently a large dipole moment) connected directly to the aromatic core. It is well known that connecting two discotic molecules together via a spacer (discotic dimers) stabilizes the columnar mesophase significantly and often leads to the formation of glassy materials. The introduction of functionality into LCs allows the variation of their properties on a wide scale and opens the route to new synthetic supramolecular systems for various device applications.
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