Synthesis of Novel Periodic Mesoporous Organosilicas Containing 1,4,5,8-Naphthalenediimides within the Pore Walls and Their Reduction To Generate Wall-Embedded Free Radicals.

Novel periodic mesoporous organosilicas (PMOs) containing 1,4,5,8-Naphthalenediimide (NDI) chromophores as an integral part of the pore walls were synthesized in acidic conditions, in the presence of inorganic tetraethyl orthosilicate, using triblock copolymer surfactant Pluronic P-123 as a template. The NDI precursor, the bridged silsesquioxane N, N'-bis(3-triethoxysilylpropyl)-1,4,5,8-naphthalenediimide, was synthesized by reaction of 1,4,5,8-naphthalenetetracarboxylic dianhydride with excess 3-aminopropyltriethoxysilane. A series of samples containing up to 19% (weight %) of NDI were prepared (the materials were labeled PMONDIs).