Fluorescent Amphiphilic Quaternized β-Chitin: Antibacterial Mechanism and Cell Imaging.

Fluorescent materials span multiple applications from biological probes and chemical sensing to optoelectronic systems. Although great efforts have been made toward developing classes of fluorescent materials, 100,000+ traditional fluorescent dyes still suffer from the obstacle of aggregation-caused quenching (ACQ). Thus, designing fluorescent materials with excellent optical performance from ACQ luminogens remains challenging. In this work, we prepared fluorescent amphiphilic quaternized β-chitin (QC-F) via nucleophilic addition between the amino groups of QC and isothiocyanate groups of fluorescein isothiocyanate (FITC). Due to the covalent anchoring of the QC backbone, steric hindrance of the bulky acetamido groups, electrostatic repulsion of the quaternary ammonium groups, and homogeneous distribution of FITC units, the FITC units were spatially and electronically isolated, and the QC-F series exhibited unique fluorescent behaviors. The QC-F series could be used to observe their interactions with microbial cells through fluorescence imaging to gain insights into the QC antibacterial mechanism. Moreover, with their favorable cytocompatibility, the QC-F series are also suitable for cell imaging. Thus, the present work will broaden the applications of chitin and conventional ACQ luminogens.