Tuning the Photophysical Properties of BODIPY Dyes and Studying Their Self-Assembly via Hydrogen Bonding

Abstract

Here, BODIPY derivatives were functionalized with barbituric acid, which has multiple hydrogen bonding abilities that are directional, to have highly ordered hydrogen bond-mediated self-assembled structures to tune BODIPY's photophysical properties. The synthesis of barbituric acid-functionalized BODIPY derivatives via Vilsmeier and Knoevenagel reactions was achieved, and the resulting compounds were characterized with FT-IR, 1H NMR, 13C NMR spectroscopy, and mass spectrometry. Hydrogen bond-mediated self-assembled structures were investigated through UV-vis and fluorescence spectrophotometry, 1H NMR spectroscopy, and a dynamic light scattering method in solution. Moreover, SEM, HR-TEM, and PXRD were used to study the self-assembly of compounds in bulk.