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Abstract: Molecular imprinted silicate materials for phosphates and phosphonates have been prepared via the sol-gel method. Guanidine functionality, with its unique combination of electrostatic and hydrogen bonding ability, were used as selective binding points in imprinted receptor cavities. We prepared the monomer 1-trimethoxysilylpropyl-3-guanidinium chloride and incorporated it into TEOS xerogels with a phosphonate template molecule. Spectroscopic analyses, including solid state 29Si NMR, found that the guanidine monomer was quantitatively incorporated into the gel. Binding affinities of various phosphate and phosphonate substrates were determined for templated and non-templated materials using HPLC analysis and a modified Bartlett assay. Molecular memory was observed and these results will be discussed along with comparative results of imprinted xerogels functionalized with amine and trimethylammonium groups. This work was performed at Sandia National Laboratories, supported by US Department of Energy under Contract No. DE-AC04-94AL85000