This study focuses on the synthesis of a class of novel biologically-inspired ionic liquids coupled with a phosphonate group containing short to long side chains (C₃–C₁₁) via the Pudovic reaction. The ionic liquids exhibited very low glass transition temperatures and were hydrophobic in character. This method has the attributes of “click” chemistry with outstanding efficiency, simplicity, yields and regioselectivity. The results of their calcium(II) ligating capability are also presented.