Highly Sensitive Water Detection Through Reversible Fluorescence Changes in a syn-Bimane Based Boronic Acid Derivative

Abstract

Reported herein is a fluorometric and colorimetric sensor for the presence of trace amounts of water in organic solvents, using syn-bimane based boronate ester 1. This sensor responds to the presence of water with a highly sensitive turn-off fluorescence response, with detection limits as low as 0.018% water (v/v). Moreover, analogously high performance was observed when compound 1 was adsorbed on filter paper, with the paper-based sensor responding both to the presence of liquid water and to humid atmospheres. Reusability of the paper-based sensor up to 11 cycles was demonstrated, albeit with progressive decreases in the performance, and 1H NMR and mass spectrometry analyses were used to explain the observed, hydrolysis-based sensor response.

A Short Review on Recent Advances and Applications of Bimane Chemistry

“…This structure, available from the Sonogashira-catalyzed cross-coupling of diiodo compound 24, responded to water in both the liquid phase and as water vapor, resulting in fluorescence quenching in both cases. 28 This response can be seen both in the solution of bimane 25 and on filter papers to which bimane 25 was adsorbed, resulting in colorimetric and fluorometric changes. The addition of water induces the fluorescence quenching of bimane 25 is mostly via the water induced hydrolysis of the boronate ester moieties on compound 25 to form the hydrolyzed boronic acid.…”

Highly tunable bimane-based fluorescent probes: design, synthesis, and application as a selective amyloid binding dye

“…22 In addition, bimane has the capability to act as an O-donor ligand in metal-bimane complexes, including those with Pd(II), Na(I), and Li(I). 23 However, with the exception of a few derivatives, [23][24][25] exploration of bimanes in complex biological applications has been limited due to their UV absorption and blue uorescence.…”