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Synthesis and Properties of Novel Crosslinkable Phthalocyanine Monomers

Polymer films incorporating phthalocyanine rings are useful for third-order nonlinear optical applications. Two axially modified silicon phthalocyanine monomers containing crosslinkable sites have been synthesized. A monomer containing acrylate groups was crosslinked thermally whereas a monomer containing cinnamate groups was crosslinked both thermally and photochemically. Both monomers can be made into solid polymeric films incorporating over 20% (w/w) of the phthalocyanine ring with no observable phase segregation. Elemental analysis, 1H NMR, FT-IR, and UV-Vis spectroscopy were employed for the structural characterization of the monomers. The kinetics of crosslinking such as reaction conversion versus time and temperature, heat of reaction (ΔH), activation energy (ΔE) and reaction order (n), and the thermal properties of the crosslinked films have also been investigated.