Glucose Sensing via Aggregation and the Use of “Knock-Out” Binding To Improve Selectivity

Abstract

Aggregates of an amphiphilic monoboronic acid bearing a hydrophobic pyrene fluorophore were employed for highly modulating, sensitive, and selective ratiometric fluorescent sensing of glucose in aqueous solution. The selectivity for glucose was improved by "knock-out" binding of fructose by phenylboronic acid.

Anion–π and Cation–π Interactions on the Same Surface

“…The absorption spectra of 1 and 2 were recorded in comparison with their protected, uncharged precursors 3 b and 3 c. The largest red shifts in response to the formation of ion pair-p interactions were, not surprisingly, observed in the least polar solvent, i.e., CCl 4 (Figure 2 c, Table 1). At high dilution, the antiparallel configuration in isomer 1 caused a red shift of Dl max =+ 41 nm.…”

“…Table 1). Solvatochromism, [9] that is excited-state stabilization by polar solvents, could be observed as a red shift of Dl max = + 19 nm from l max = 421 nm to l max = 440 nm for control 3 b in CCl 4 and DMSO (Figure 2 a and c, dashed lines, Table 1). For the same change in solvent polarity, the antiparallel carboxylate-guanidinium pairs in 1 produced a small blue shift of Dl max = À9 nm from l max = 462 nm to l max = 453 nm, possibly due to weakened ion pair-p interactions in these more competitive solvents (Figure 2 a and c, solid lines, Table 1).…”

“…However, the combination of anions and cations near aromatic rings has been reported in the context of molecular recognition, [3,4] the spectral tuning of green-, red-, and cyan-fluorescent protein probes, [5] and the understanding of firefly luciferase [6] as well as the chemistry of vision.…”

Controlled self-assembly of small molecule probes and the related applications in bioanalysis

“…Sugars can also induce aggregation of the pyrene probes and result in excimer formation (Huang et al, 2013;Neupane et al, 2014). For example, Huang et al (2013) prepared a pyrene probe (Py-B) modified with a monoboronic acid receptor and a cationic pyridinium moiety (Fig.…”

“…For example, Huang et al (2013) prepared a pyrene probe (Py-B) modified with a monoboronic acid receptor and a cationic pyridinium moiety (Fig. 20).…”