Polydiacetylenes (PDAs) have attracted great interest due to their potential uses as advanced materials, such as chemical/bio sensors, nano wires or nonlinear optical materials, etc. PDAs are commonly prepared by 1,4 polymerization of diacetylene monomers in the solid state. Recently, we have reported the first single-crystal-to-single-crystal polymerization of a terminal diacetylene. Herein, a series of new terminal diacetylene monomers, including aryl terminal diacetylenes have been prepared. They have been successfully arranged via host-guest chemistry in patterns suitable for solid state 1,4 polymerization. The heat-induced polymerization of these diacetylenes is being carefully investigated.