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

Luna Yang; Yifan Wang; Chenhao Wang; Feng Liu; Weiping Chen; Yonggang Wu; Hongchi Zhao

doi:10.1071/CH24146

RESEARCH ARTICLE

Next Contents Vol 78(3)

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

Luna Yang ^A , Yifan Wang ^A , Chenhao Wang ^B , Feng Liu

^B ^* , Weiping Chen ^A , Yonggang Wu ^A and Hongchi Zhao ^A ^*

+ Author Affiliations

- Author Affiliations

^A College of Chemistry and Materials Science, Hebei University, Baoding, 071002, PR China.

^B School of Basic Medical Sciences, Hebei University, Baoding, 071002, PR China.

^* Correspondence to: liufeng@hbu.edu.cn, zhc@hbu.edu.cn

Handling Editor: Martyn Coles

Australian Journal of Chemistry 78, CH24146 https://doi.org/10.1071/CH24146

Submitted: 7 October 2024 Accepted: 24 February 2025 Published online: 14 March 2025

Abstract

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⁻, ${NO}_{3}^{-}$ , AcO⁻, ${BF}_{4}^{-}$ , ${PF}_{6}^{-}$ , ${ClO}_{4}^{-}$ , $H_{2} {PO}_{4}^{-}$ and ${SO}_{4}^{2 -}$ . 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.

Keywords: BN substituted fluoride anion detection, cell imaging, cytotoxicity, fluorescence probe, fluorescence quenching, PDIs, perylene diimides, Suzuki coupling reaction.

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

Abstract

References

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