Amphiphilic and Zwitterionic Multi Arylpyrroles with Near-Infrared Aggregation-Induced Emission for Cell Membrane Imaging

The cell membrane protects the cell stability and balance and participates in various physiological activities as an exchange channel. Therefore, the real-time monitoring of cell membrane biological dynamics can help us understand the physiological state of the current cell. Herein, a type of amphiphilic near infrared (NIR) aggregation-induced emission (AIE) molecules was designed and synthesized. Multiarylpyrroles (MAPs) with a dodecyl chain at the 1-position of the pyrrole ring, charged pyridinium sulfonate at the 2,5-position of the pyrrole ring and free rotating aryls at the 3-position of the pyrrole ring can target cell membranes. One of the MAPs, MAP22, had a maximum emission wavelength in the aggregation state of up to 721 nm with a large Stokes shift (similar to 280 nm). In addition, MAP22 nanoparticles can produce reactive oxygen species (ROS) with a quantum yield of 224%. Therefore, these AIE MAPs are promising candidates for theranostic nanoagents, including NIR fluorescence imaging to target cell membranes and ablate cancer cells by producing ROS.