Fluorescent carbazole-containing dyes: Synthesis and supramolecular assembly by self-complementary donor-acceptor π-stacking and dipolar interactions

Six carbazole-based dyes were synthesized by fluorescence turn on amino-ene click reactions. Two high quality single-crystals of new dyes were prepared, and their X-ray diffraction structure analyses reveal the formation of antiparallel stacking superstructures driven by self-complementary dipole-dipole and π-stacking interactions between carbazole donors and acceptors. The optical behaviors and donor-acceptor interactions of these dyes were investigated by ultraviolet–visible absorption, fluorescence emission spectroscopy, and electrochemical cyclic voltammetry. Blue fluorescence appears and increases as dye-based supramolecular polymer grows, as revealed by dynamic light scattering, fluorescence, 1H NMR and 2D NMR spectroscopy. Single-crystal X-ray diffraction analysis reveals that the carbazole-based dyes are assembled into an antiparallel supramolecular structure by self-complementary dipole-dipole and π-π stacking interactions between donor and acceptor. Blue fluorescence appears and increases as supramolecular polymer grows. [Display omitted] •Six carbazole-containing dyes were synthesized by fluorescence turn on amino-ene click reactions•Two high quality single crystals were prepared. Their X-ray diffraction structure analyses reveal that the carbazole-based dyes are assembled into an antiparallel supramolecular structure by self-complementary dipole-dipole and π-stacking interactions between donor and acceptor.•Blue fluorescence appears and increases as dye-based supramolecular polymer grows.