Synthesis of some novel heteroarylene ethynylene polymers containing 1,10-phenanthroline in the polymer backbone

Palladium-catalyzed polycondensation between 3,8-dibromo-1,10-phenanthrolin e and substituted phenyl-1,4-diacetylenes in the presence of diisopropylami ne produced the soluble pi-conjugated poly(heteroarylene ethynylene)s 7a an d 7b. The polymers were obtained in high yields (86-92%) and had molecular weights of (M) over bar(n) = 8700 g . mol(-1) (7a; vapor pressure osmometry ) and 6900 g . mol(-1) (7b; vapor pressure osmometry). The low molecular mo del compounds 6a and 6b were prepared to analyze the connection between the primary structure and spectroscopic properties. (C) 1999 John Wiley & Sons , Inc.