Fluorenone-based organogel and self-assembled fibrous film: Synthesis, optical properties and reversible detection of aniline vapor

Two new low-molecular mass organic gelators (LMOGs) based on fluorenone and 3,4,5-tris(dodecyloxy)benzamide auxiliary group (SOF and DOF) were synthesized and characterized. Their photophysical properties were investigated systematically via spectroscopic and theoretical methods. Both compounds exhibit ¹π,π* transitions in the UV region, and broad, structureless intramolecular charge transfer (¹ICT) absorption bands in the visible spectral region. Both compounds are emissive in solution at room temperature, which can be attributed to ¹ICT state. In addition, the gel properties of the two compounds in 10 solvents was studied. Compared to SOF with a single auxiliary group, DOF bearing two auxiliary groups are easier to form gels in different solvents. Fluorescence behavior and sensing performance studies of DOF xerogel film obtained by self-assembling demonstrated that this film is chemically stable, and reversible and selective to the presence of aniline vapor through the photoinduced electron transfer (PET) mechanism. The self-assembled properties of the LMOGs will be more conducive to the functionalization of photofunctional materials.