Methyl Cinnamate-Derived Fluorescent Rigid Organogels Based on Cooperative π-π Stacking and C═O···π Interactions Instead of H-Bonding and Alkyl Chains.

A new class of rigid low-molecular-mass organic gelators (LMOGs) was synthesized by McMurry and Heck reactions, and their gels and photophysical properties were investigated. The LMOGs lacked alkyl chain and H-bonding units and produced good gelation ability in selected mixed organic solvents facilitated by cooperative π-π stacking and C═O···π interactions. Sensitive gel-sol transformation by molecular aggregation and disaggregation was easily achieved upon heating and cooling. H-H 2D NOESY and X-ray diffraction (XRD) patterns showed the π-π stacking and C═O···π interactions between tiny methyl acrylate groups as "tails". Importantly, this soft interaction model offers a useful tool for the future design and construction of supramolecular structures. At present, the LMOGs reported herein offer a sensitive gel-formation ability and aggregation-induced emission (AIE) property and thus have promising application potentials as functional soft matter in amorphous materials, photoelectric materials, and so on.

CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides.

In this study, a facile CuI catalyzed synthesis of sulfones involving a nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides is realized. This reaction proceeds efficiently at room temperature, giving rise to various functional group substituted sulfones, generally in moderate to high yields. The method provides a novel, simple, and promising strategy for functionalized sulfone synthesis in the research field of sulfur chemistry.