Synthesis and Characterization of Poly(2,6-triptycene)

We report the syntheses of two monomers, 2,6-dibromotriptycene and 2,6-diiodotriptycene, and their applications in the homopolymn. via a nickel(0)-mediated Yamamoto-type polycondensation polymn., leading to a novel arom. polymer-poly(2,6-triptycene). This new polymer was characterized by 1H and 13C NMR spectroscopy, which exhibited an excellent match with the NMR spectra of the model compd., 2,2′-bitriptycene. In addn., the polymer was found to be highly sol. in common org. solvents, although it does not contain any flexible side chains. This good soly. was attributed to its high content of triptycene units, whose rigid three-dimensional structure was proposed to prevent dense packing of polymer chains. A highly transparent film could be obtained by spin-casting a chloroform soln. This polymer also demonstrated good thermal stability. [on SciFinder(R)]