Macromolecules, Vol.39, No.19, 6445-6450, 2006
Multicyclic polyethers derived from 1,4-dicyanotetrafluorobenzene and flexible diphenols
1,4-Dicyanotetrafluorobenzene (DCTB) was polycondensed with various diphenols in DMF or DMSO using K2CO3 as catalyst and HF acceptor. At concentrations of 0.1 or 0.2 mol/ L for DCTB, gels were obtained with 1,4-bis[2-(4-hydroxyphenyl)-2-propyl] benzene, with 1,3-bis[(4-hydroxyphenyl)- 2- propyl] benzene and with alpha,omega-bis(4-hydroxyphenoxy) alkanes as comonomers. Yet soluble multicyclic polyethers were formed with alpha,omega-bis(3-hydroxyphenoxy) alkanes. The lengths of the alkane chains did not play any role for the successful syntheses of soluble multicycles. Furthermore, a model reaction with p-cresol was conducted, proving the feasibility of a quantitative tetrasubstitution of all four F-atoms in DCTB. The multicyclic polyethers were characterized by elemental analyses, C-13 NMR spectroscopy, MALDI-TOF mass spectrometry, DSC, viscosity, and SEC measurements. As expected, high polydispersities (up to 8) were found. The DSC measurements indicated an amorphous character of all multicycles with glass-transition temperatures (Tgs) between 75 and 161 degrees C.