N,N,N ',N '-tetrakis(2-pyridylmethyl)-1,2-ethylenediamine (TPEN) has been shown previously to exhibit a high separation factor for the separation of americium (III) and europium (III). Application of TPEN is limited due to the solubility of the material under acidic conditions (pH < 4). A variety of analogs were synthesized in this study to examine effects caused by various structural modifications in an effort to retain the selectivity of the parent compound while decreasing solubility in acidic media. Results indicate that the substitution at the ethylene linker of TPEN eliminates the ability of the compound to separate americium (III) over europium (III).