A latent reversible ratiometric optical pH sensing probe based on phenylboronic acid for alkaline pH detection and applications in test paper and alkalotic HK-2 cells

Abstract

Metabolic alkalosis, the most common acid–base disorder, is related to significantly increased mortality in hospitalized patients. Hunting for pH sensors lying in the neutral to alkaline pH range still remains challenging and in demand. Herein, we engineered a colorimetric/fluorescent method for monitoring alkalic pH based on a phenylboronic acid-containing probe (DDPB). In this approach, the dicyanoisophorone group of DDPB acted as an optical signal moiety, while the boronic acid acted as the latent pH response site. It was exactly deciphered that the reversible pH monitoring principle is based on the deprotonation/protonation mechanism and intramolecular charge transfer (ICT) strategy via¹H NMR and DFT calculations. This approach presented a pH-sensitive response over pH values ranging from 7.00 to 10.23 (pK_a = 9.33) with excellent reversibility. We further explored its application in sensing pH on a paper substrate for visual and rapid detection. In addition, it was successfully applied to measure pH variations in HK-2 cells when the cells underwent alkalosis. This work extends the application of optical probes based on boronic acid under alkaline pH conditions, and provides a new strategy for the design of alkaline pH probes.