Templated Synthesis of Electroactive Periodic Mesoporous Organosilica Bridged with Oligoaniline

The synthesis and characterization of novel electroactive periodic mesoporous organosilica (PMO) are reported. The silsesquioxane precursor, N,N'-bis(4'-(3-triethoxysilylpropylureido)phenyl)-1,4-quinonene-diimine (TSUPQD), was prepared from the emeraldine base of amino-capped aniline trimer (EBAT) using a one-step coupling reaction and was used as an organic silicon source in the co-condensation with tetraethyl orthosilicate (TEOS) in proper ratios. By means of a hydrothermal sol-gel approach with the cationic surfactant cetyltrimethyl-ammonium bromide (CTAB) as the structure-directing template and acetone as the co-solvent for the dissolution of TSUPQD, a series of novel MCM-41 type siliceous materials (TSU-PMOs) were successfully prepared under mild alkaline conditions. The resultant mesoporous organosilica were characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetry, X-ray diffraction, nitrogen sorption, and transmission electron microscopy (TEM) and showed that this series of TSU-PMOs exhibited hexagonally patterned mesostructures with pore diameters of 2.1-2.8 nm. Although the structural regularity and pore parameters gradually deteriorated with increasing loading of organic bridges, the electrochemical behavior of TSU-PMOs monitored by cyclic voltammetry demonstrated greater electroactivities for samples with higher concentration of the incorporated TSU units.