Boronic acids (BAs) can form reversible covalent linkages to 1,2- and 1,3-diols which in particular present in sugars. In the process of binding diols, BAs become considerably more acidic, with pKa decreases of 2-4 units. The binding-induced change in BA acidity can induce changes in solution pH, electrostatic interactions and surface charge. These properties may ultimately be useful for optical, conductimetric, and field-effect transistor-based glucose sensing. However, mono BAs (MBAs) show higher affinity to other interferential sugars in blood than glucose. Diboronic acids (DBAs) with molecular architectures have been developed with better selectivity toward glucose, however, reported DBAs with good selectivity lost the ability to change pKa around physiological pH. Thus we designed a new diboronic acid molecule, DBA+, which exhibits good affinity (Kd ≈ 1 mM) and selectivity toward glucose, and can changes the pKa from 9.4 to 6.3 upon binding with glucose. The properties of DBA+ enable opportunities for glucose detection based on the charge reversion at physiological pH.