The synthesis and characterization of the first BODIPY appended to the five-membered heterocylic tellurophene [Te] moiety is reported. By incorporating tellurophene at the meso position, the tellurophene-appended boron-dipyrromethene dye (BODIPY) acts as a multimodal agent, becoming a potent photosensitizer with a mass cytometry tag. To synthesize the compound, we developed a method to enable late-stage Suzuki–Miyaura coupling by preparing and isolating tellurophene-2-BPin in a one-step procedure from the parent tellurophene. Coupling to a meso-substituted BODIPY functionalized with a pendant aryl bromide provides the desired tellurophene-appended BODIPY. This compound demonstrated a singlet oxygen quantum yield of 0.26 ± 0.01 and produced a light dose-dependent cytotoxicity with nanomolar IC50 values against 2D cultured HeLa cells and high efficacy against 3D cultured HeLa tumor spheroids, proving to be a strong photosensitizer. The presence of the tellurophene moiety could be detected using mass cytometry, thus showcasing the ability of a tellurophene-appended BODIPY as a novel photodynamic-therapy–mass-cytometry theranostic agent.

Reported herein are the synthesis and characterization of BODIPYs bearing heterocycles at boron. To synthesize this series, various chalcogenophenes (furan, thiophene, selenophene, and tellurophene) were lithiated and then used as nucleophiles to attack the boron center of a parent F-BODIPY. Compounds in the series were compared with respect to their photophysical and structural properties, and trends were discussed. By virtue of the "heavy atom effect", as the mass of the heterocycle appended to the BODIPY core increases, compounds exhibit a higher singlet oxygen quantum yield. The BODIPY with tellurophene at boron exhibits the highest quantum yield (Φ Δ = 0.68) in the series and reduced emission (Φ f = 0.01).

Gemini surfactants are composed of two hydrocarbon tails with corresponding polar headgroups, linked via a covalent spacer. The synthesis of these surfactants is a very active area of research due to their application as catalysts and other applied areas of study. The modification of green microwave techniques developed in our research on ionic liquids has resulted in the significant improvement of the synthesis of N,N ′-bis(dimethylalkyl)-α,ω-alkanediammonium dibromide (m–s–m type) symmetrical gemini surfactants. This approach utilizes a remarkably more economical, green, and sustainable methodology for the production of symmetrical gemini surfactants that can be utilized in numerous commercial applications. The improved synthetic approach of these gemini surfactants has led to the characterization of their crystalline packing for the first time ever using X-ray crystallographic analysis.