Synthesis of 4-(2-triphenylaminovinyl) Phenoxy Derivative

Triphenylamine derivatives and quaternary ammonium salt-based antimicrobial peptide mimics are two types of antimicrobial molecules with broad application prospects. The incorporation of these derivatives endows them with inherent fluorescence imaging capabilities and photodynamic antibacterial activity, thus achieving the integration of therapeutic and diagnostic functions. Through this modification, the compound acquires the ability to mimic the physical membrane disruption mechanism of antimicrobial peptides, exhibits broad-spectrum and highly effective antimicrobial activity, and reduces the tendency to induce drug resistance. In this work, triphenylamine quaternary ammonium salt derivatives (TPQ) were designed and synthesized through four consecutive reactions: Wittig reaction, Heck reaction, substitution reaction, and quaternization reaction. Double bonds, hydroxyl groups, brominated alkyl chains, and quaternary ammonium groups were gradually introduced to finally obtain the target product (E)-2-(4-(4-(diphenylamino)styryl)phenoxy)-N,N,N-trimethyloctan-1-aminium (7). This study provides new insights into the development of antimicrobial agents with excellent biocompatibility.