SYNTHESIS AND POLYMERIZATION OF COUPLED COMPOUNDS OF 1,11-DODECADIYNE

The dimer, trimer, and tetramer of 1,11-dodecadiyne, HC=C-(CH2)(8)-C=C H, were synthesized. The solid-state polymerization of the dimer was i nvestigated by infrared (IR) spectroscopy. IR bands due to the diacety lene moiety were identified through the comparison of the IR spectra o f the dimer, trimer, and tetramer. The dimer was found to have two pol ymorphs, melt-crystallized and solution-crystallized. Both of the poly morphs undergo solid-state polymerization by exposure to gamma-ray or UV irradiation. The former has higher polymerizability for the diacety lene moiety than the latter. The solid-state polymerization of the ter minal acetylene group was not observed. It is shown that the previousl y reported dimer structure in which both the diacetylene and terminal acetylene groups are polymerized to form an inherently electrically co nducting polymer is incorrect. (C) 1995 John Wiley and Sons, Inc.