Fluorescent BF₂ Complexes Inspired by Ageladine A

Abstract

Abstract. The pH‐dependent UV/Vis absorption and fluorescence of several analogs of the marine natural product ageladine A were investigated. Besides ageladine A itself, its BF2 complex, and the corresponding debrominated analogs were included, as were the chloro analog of the debromoageladine‐BF2 complex, an imidazolone analog, and a triazole derivative, which lack the free amino group. Importantly, the pH‐dependence of the fluorescence of the chloro analog closely resembles that of the natural product ageladine A, but with about 25‐fold higher fluorescence intensity and a maximum between pH 3 and 6. The imidazolone derivative behaves in a complementary manner and shows fluorescence only above pH 6, but with less intensity than ageladine A. The calculated Stokes shifts agrees well with the experiment, which underlines the accuracy of the DFT calculation method (ωB97XD/TApr‐cc‐pVDZ, water, PCM). The combination of BF2 units with arylated imidazo[4,5‐c]pyridine structural motifs encourages further research on more strongly fluorescent derivatives of comparable molecular size.