Synthesis of novel mono BN substituted symmetrical and asymmetrical perylene diimides for fluoride anion detection

Three novel mono BN substituted perylene diimide (PDI) derivatives, namely PDI-BN1, PDI-BN2 and PDI-BN3, were designed and efficiently synthesised using a concise synthetic strategy. Their molecular structures were confirmed by NMR, high-resolution mass spectrometry and FTIR. The electronic and optical characteristics were also comparatively studied. These BN substituted PDI derivatives exhibited orange fluorescence, with their properties finely adjustable by integrating various fused aryl rings. Except for F− ions, all the BN substituted PDI derivatives have shown no affinity for other anions, such as Cl−, Br−, I−, NO3−, AcO−, BF4−, PF6−, ClO4−, H2PO4− and SO42−. Cytotoxic evaluation on HeLa cells revealed that PDI-BN1 was found to be non-toxic, and cellular imaging studies were carried out to authenticate the real applicability of PDI-BN1 in F− ion detection.