Design And Synthesis Of Fluorescent Dyes Based On Rylene Bisimide Substituted On The Bay Region And The Research Of Their Properties

Higher rylene diimide dyes have been a chromophore with potential applications in various research fields due to their exceptional photoelectric properties, thermal and photochemical stabilities. So we prepared the rylene bisimide with substituted groups on the bay region. Details are as follows:1. Perylenedicarboximides lined in the free peri-position to dyads were modified by PEG chain to get compound PDPDI, then we got compound GDPDI by guanidinylating the PEG chain. PDPDI is insoluble in the water due to the strong aggregation, while GDPDI with polycationic dendrons which can inhibit the aggregation behaviors has high water-solubility.The peri-linking of perylene dyes substituted in the bay region exhibited a red fluorescence with increasing the Stokes Shifts from 34 nm to 100 nm. The GDPDI dyes showed over 98%cell viability, indicating good biocompatibility. GDPDI dyes can be efficiently internalized by live cells, which can be used for bioimaging.2. We synthesized quaterrylendiimides(QDI), then ether groups, sulfide groups,sulfoxide groups and sulfone groups were introduced into the bay region of quaterrylendiimides to get four compounds(QDI-4S, QDI-4SO, QDI-4SO2, QDI-4O). We researched their solubility and optical properties which showed their absorption and emission peak generated bathochromic shift. Among of them, the absorption and emission peak of quaterrylendiimides substituted with sulfone groups generated the largest bathochromic shift with 47 nm and 24 nm. The quaterrylendiimides with sulfide substituents showed a reduced fluorescent quantum yields(4%), while the quaterrylendiimides with sulfoxide substituents exhibited a improved fluorescent quantum yields(28%). The photostability of quaterrylendiimides compounds was excellent photostability.