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

doi:10.1016/j.saa.2021.119881

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

King Abdullah University of Science and Technology

Research output: Contribution to journal › Article › peer-review

17 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 language	English (US)
Pages (from-to)	119881
Journal	Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy
Volume	259
DOIs	https://doi.org/10.1016/j.saa.2021.119881
State	Published - 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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10.1016/j.saa.2021.119881

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Ullah, Z., Sonawane, P. M., Nguyen, T. S., Garai, M., Churchill, D. G., & Yavuz, C. T. (2021). Bisphenol–based cyanide sensing: Selectivity, reversibility, facile synthesis, bilateral “OFF-ON” fluorescence, C2ν structural and conformational analysis. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 259, 119881. https://doi.org/10.1016/j.saa.2021.119881

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

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.",

author = "Zakir Ullah and Sonawane, {Prasad M} and Nguyen, {Thien S} and Mousumi Garai and Churchill, {David G} and Yavuz, {Cafer T}",

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.",

year = "2021",

month = may,

day = "10",

doi = "10.1016/j.saa.2021.119881",

language = "English (US)",

volume = "259",

pages = "119881",

journal = "Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy",

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Ullah, Z, Sonawane, PM, Nguyen, TS, Garai, M, Churchill, DG & Yavuz, CT 2021, 'Bisphenol–based cyanide sensing: Selectivity, reversibility, facile synthesis, bilateral “OFF-ON” fluorescence, C2ν structural and conformational analysis', Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, vol. 259, pp. 119881. https://doi.org/10.1016/j.saa.2021.119881

Bisphenol–based cyanide sensing: Selectivity, reversibility, facile synthesis, bilateral “OFF-ON” fluorescence, C2ν structural and conformational analysis. / Ullah, Zakir; Sonawane, Prasad M; Nguyen, Thien S et al.
In: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, Vol. 259, 10.05.2021, p. 119881.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Bisphenol–based cyanide sensing: Selectivity, reversibility, facile synthesis, bilateral “OFF-ON” fluorescence, C2ν structural and conformational analysis

AU - Ullah, Zakir

AU - Sonawane, Prasad M

AU - Nguyen, Thien S

AU - Garai, Mousumi

AU - Churchill, David G

AU - Yavuz, Cafer T

N1 - 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.

PY - 2021/5/10

Y1 - 2021/5/10

N2 - 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.

AB - 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.

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UR - https://linkinghub.elsevier.com/retrieve/pii/S1386142521004571

UR - http://www.scopus.com/inward/record.url?scp=85105481636&partnerID=8YFLogxK

U2 - 10.1016/j.saa.2021.119881

DO - 10.1016/j.saa.2021.119881

M3 - Article

C2 - 33971439

SN - 1386-1425

VL - 259

SP - 119881

JO - Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy

JF - Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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