Cooling-Induced NIR Emission Enhancement and Targeting Fluorescence Imaging of Biperylene Monoimide and Glycodendrimer Conjugates

Under high concentrations, strong pressure, and low temperature, fluorophores usually exhibit the fluorescence quenching phenomenon. Of significance, the development of aggregation-induced emission (AIE) and pressure-induced emission (PIE) fluorophores has perfectly prevented fluorescence quenching under high concentrations and strong pressure. However, cooling-induced fluorescence quenching in water is still an urgent problem. In this paper, cooling-induced emission (CIE) enhancement based on a biperylene monoimide (BPMI) derivative, BPMI-18Lac, with a conjugated lactose-based glycodendrimer was developed. BPMI-18Lac, as a non-AIE molecule, exhibited the CIE phenomenon with a fluorescent intensity increasing 7-fold when the temperature decreased from 80 to ？40 °C. The mechanism was due to the inhibition of the intramolecular electron interactions between the perylene monoimide moieties linked by the C–C single bond. In addition, BPMI-18Lac, as a multivalent glycodendrimer, showed selective fluorescence imaging for HepG 2 cells through the ASGP receptor on the cell surface. Importantly, this work developed a water-soluble CIE molecule for potential application below freezing temperature