The interaction of N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine with carboxylic acids resulted in a new series of dicationic protic alkanolammonium ionic liquids (PAAILs). New PAAILs were characterized by NMR, FTIR spectroscopy, and thermal analysis. The conformation of N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediammonium cations and intermolecular interactions in salts of 1-hydroxy-2-naphthoic and oxalic acids were studied using X-ray diffraction supplemented by Hirshfeld surfaces analysis. Some pharmacokinetic parameters of the synthesized dicationic PAAILs have been predicted to evaluate their potential biomedical applications. In comparison with monocationic PAAILs, their antimicrobial and buffering activity in ⁶⁸Ga-radiolabeling reactions of chelating agents and clinically relevant peptides were studied.