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Anionic Surfactant-Triggered Excimer Emission from Dipyrene-Based Amphiphilic Dyes for Wash-Free Cell Membrane
Yongling Zheng1, Bailin Guo1, Enju Wang2
1Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou, 571158, P. R. China.
None:
Compared to monomer emission, excimer emission usually exhibits red-shifted, broadened, and large Stokes-shifted characteristics, which offer distinct advantages in biological imaging. In this work, we developed a rational design strategy for excimer-based cell membrane fluorescent probes, and on this basis, three fluorescent dyes (BPVP-C3, BPVP-C5 and BPVP-C8) exhibiting tunable excimer/monomer emission were obtained by covalent coupling of two pyrene units. In sodium dodecyl sulfate micelles, these fluorophores show bright excimer emission, whereas in dilute aqueous solutions, they emit monomer-dominated fluorescence. We proposed that the anionic micellar environment promotes intramolecular excimer formation between coupled pyrene units due to its balanced amphiphilicity, while these dye molecules can freely swing in dilute aqueous solution. Among them, BPVP-C8 exhibited optimal excimer-monomer switching property. Leveraging this environment-responsive dual-emission, it was explored as a wash-free cell membrane probe for simultaneous dual-channel (green and red) imaging.
