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

摘要

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 pi-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, H-1 NMR and 2D NMR spectroscopy.