<span style="mso-fareast-font-family: 'Abadi Extra Light';">Design and Synthesis of Arylboronic Acid Chemosensors for the Fluorescent-Thin Layer Chromatography (f-TLC) <span style="mso-bookmark: _Hlk186185499;"><span style="mso-fareast-font-family: 'Abadi Extra Light';">Detection of <span style="mso-bookmark: _Hlk186185499;"><span style="mso-fareast-font-family: 'Abadi Extra Light';">Mycolactone

Fluorescent chemosensors are increasingly becoming relevant in recognition chemistry due to their sensitivity, selectivity, fast response time, real-time detection capability, and low cost. Boronic acids have been reported for the recognition of mycolactone, the cytotoxin responsible for tissue damage in Buruli ulcer disease. A library of fluorescent arylboronic acid chemosensors with various signaling moieties with certain beneficial photophysical characteristics (i.e. aminoacridine, aminoquinoline, azo, BODIPY, coumarin, fluorescein, and rhodamine variants); and a recognition moiety (i.e. boronic acid unit) were rationally designed and synthesized using combinatorial approaches; purified and fully characterized using a set of complementary spectrometric and spectroscopic techniques such as NMR, LC-MS, FT-IR, and X-ray crystallography. In addition, a complete set of basic photophysical quantities such as absorption maxima (labsmax), emission maxima (lemmax), Stokes shift (∆&lambda;), molar extinction coefficient (&epsilon;), fluorescence quantum yield (&Phi;F), and brightness were determined using UV-vis absorption and fluorescence emission spectroscopy techniques. The synthesized arylboronic acid chemosensors were investigated as chemosensors for mycolactone detection using the fluorescent-thin layer chromatography (f-TLC) method. Compound 7 (with a coumarin core) emerged the best (labsmax = 456 nm, (lemmax = 590 nm, ∆&lambda; = 134 nm, &epsilon; = 52816 M-1cm-1, &Phi;F = 0.78, and brightness = 41197 M-1cm-1).