We report on a new approach for creating water-soluble functionalized vesicles employing N-alkyl-3-boronopyridinium triflates (alkyl = Me, C12H25, C16H33) as sensors for monosaccharides. The nanoaggregate properties were studied by means of DLS, TEM, high-resolution (1)H NMR, and the solvatochromic dyes Reichardt's betaine and Methyl Orange. The vesicles were shown to have 30-200 nm diameters depending on the amphiphile chain length. Diol binding to the vesicles was studied by steady-state fluorescence and UV-vis using Alizarin Red S as a probe in the solution at pH 7.4 in the presence and in the absence of D-glucose and D-fructose. Strong sensing ability of boronic acid functional moieties in the order D-fructose > D-glucose was demonstrated, and apparent binding constants were estimated.

In this paper, we describe a simple and efficient procedure of original N‐alkyl‐3‐boronopyridinium triflates synthesis and report on the surface properties of these surfactants. Key micellar parameters were obtained, the critical micelle concentrations (CMC values) were determined and compared to conventional ionic surfactants as well as the surface activity of these surfactants (pC20 value and the surface tension at the CMC). These new boronic functionalized surfactants exhibit a stunning efficiency in their tendency to self‐assemble and are significantly more surface active that their conventional analogues. This new family of surfactants represents a new direction in both functionality and performance, and may open perspectives in chemical synthesis and applications.