Bisphenol–based cyanide sensing: Selectivity, reversibility, facile synthesis, bilateral “OFF-ON” fluorescence, C2ν structural and conformational analysis

Zakir Ullah, Prasad M Sonawane, Thien S Nguyen, Mousumi Garai, David G Churchill, Cafer T Yavuz

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

A structurally characterized novel dual–pocketed tetra–conjugated bisphenol–based chromophore (fluorescence = 652 nm) was synthesized in gram scale in ~90% yield from its tetraaldehyde. Highly selective, naked-eye detection of CN− (DMSO/H2O) was confirmed by interferent testing. A detection limit of 0.38 µM, within the permissible limit of CN− concentration in drinking water was achieved as mandated by WHO. The “reversibility” study shows potential applicability and reusability of Sen. Moreover, cost-effective and on-site interfaces, application tools such as fabricated cotton swabs, plastic Petri dishes, and filter papers further demonstrated the specific selectivity of Sen for the toxic CN−. In addition, an easily available and handy smartphone-assisted “Color Picker” app was utilized to help estimate the concentration of CN− ion present. A dual phenol deprotonation mechanism is active and supported by 1H NMR spectroscopic data and DFT calculation results.
Original languageEnglish (US)
Pages (from-to)119881
JournalSpectrochimica acta. Part A, Molecular and biomolecular spectroscopy
Volume259
DOIs
StatePublished - May 10 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-06-11
Acknowledgements: This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean government (MSIP) (No. NRF-2017M3A7B4042140 and NRF-2017M3A7B4042235) and the start-up funds provided by the King Abdullah University of Science and Technology (KAUST). D.G.C appreciates financial support and resources from KAIST and the International Joint Usage Project with ICR, Kyoto University (2019-115 and 2020-124) for the operation of the Molecular Logic Gate Laboratory to make this work possible. P.M.S. acknowledges the KGSP of Korea.

ASJC Scopus subject areas

  • Instrumentation
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Analytical Chemistry

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