Donor–Acceptor Assembly of Amphiphilic Molecules Based on 9,10-Distyrylanthracene Derivatives with Terminal Naphthalene Groups

Abstract

Amphiphilic rod−coil compounds have excellent photophysical properties and can be assembled into supramolecular nanostructures of different sizes in water or polar solvents. Herein, we synthesized the amphiphilic compounds 2N-DSA, 4N-DSA, and 6N-DSA with 9,10-distyrylanthracene (DSA) as the core and a naphthalene unit as the terminal group that connected DSA through a tetraethylene glycol chain. These compounds have excellent aggregation-induced emission (AIE) properties in aqueous solution and are assembled into worm-like fragments or different sizes of spherical assemblies, defending the volume ratio of the rod to coil segments. Notably, the donor−acceptor interaction between DSA and electron-deficient compounds 2,4,6-trinitrophenol (TNP), 2,4,5,7-tetranitrofluorenone (TNF), and tetraethylene glycol dinitrobenzoate (TGDNB) forms a charge transfer complex, which can be used as a nanoreactor to improve the yield of the Suzuki coupling reaction about 8−10 times. The experimental results reveal that the synergy effect of the donor−acceptor, intermolecular π−π stacking, and hydrophobic−hydrophilic interactions significantly influences the morphology of aggregates and the efficiency of the nanoreactor.