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 ...