Synthesis and thermal cyclopolymerization of heterocycle containing bis-ortho-diynyl arenes

A new class of heteroatom terminated bis-ortho-diynyl arene (BODA) compounds have been synthesized via efficient in situ palladium catalyzed cross coupling between tetra alkynyl silanes and aryl bromides and iodides. BODA monomers undergo Bergman-type cyclization upon heating, and afford processable intermediates and ultimately network polymers. The new heterocycle terminated oligomers are compared to phenyl terminated derivatives and exhibit bathochromic shifts (25 nm) in their emission spectra.