The high selective chemo-sensors for TNP based on the mono- and di-substituted multifarene[2,2] with different fluorescence quenching mechanism

Fei Qiu; Yin-Hui Huang; QingMei Ge; Mao Liu; Hang Cong; Zhu Tao

doi:10.1016/j.saa.2019.117583

The high selective chemo-sensors for TNP based on the mono- and di-substituted multifarene[2,2] with different fluorescence quenching mechanism

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Feb 5:226:117583. doi: 10.1016/j.saa.2019.117583. Epub 2019 Oct 13.

Authors

Fei Qiu¹, Yin-Hui Huang¹, QingMei Ge¹, Mao Liu¹, Hang Cong², Zhu Tao¹

Affiliations

¹ Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, 550025, PR China.
² Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, 550025, PR China. Electronic address: hcong@gzu.edu.cn.

PMID: 31655370
DOI: 10.1016/j.saa.2019.117583

Abstract

The chem-sensors, based on the triazole-CH₂-anthracene-functionalized multifarene[2,2] were successfully synthesized, which could efficiently and rapidly detect 2,4,6-trinitrophenol (TNP). The high specificities of the proposed macrocyclic sensors were achieved by selective response for TNP in the existence of other competing phenolic compounds, and the limits of detection in ∼10^-8 mol/L range were produced to confirm the high sensitivities of the chem-sensors, which could be attributed to the mechanism of electron and resonance energy transfer processes in the complexes with the supramolecular interactions. ¹H NMR titration analysis revealed the actual binding position should be the triazole rings of sensors with the hydroxyl group on TNP to offer a hydrogen bonding. The extraordinary sensing properties endued the compounds as sensitive fluorometric chem-sensors for the potential application of TNP detection.

Keywords: 2,4,6-Trinitrophenol; Fluorometric chemosensor; Molecular recognition; Multifarene; Supramolecular chemistry.