Journal of the American Chemical Society
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analyte detection in a flow. An insoluble polymer 10 carrying a
1b fragment was prepared using a commercial cross-linked
poly(4-vinylpyridine). When a thiol solution passed through a
plug of 10, compound 11 was quantitatively formed and its
amount, and hence the amount of thiol, could be quantified by
(2) Chan, J.; Dodani, S. C.; Chang, C. J. Reaction-based small-
molecule fluorescent probes for chemoselective bioimaging.
Nature Chem. 2012, 4, 973−984.
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Principles, Strategies, and Applications. ed; Wang, B.; Anslyn, E.
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measuring the fluorescence quenching of
downstream cuvette (Figure 5b, and Figure S46).
I located in a
(
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Chem. Rev. 2015, 115, 7893-7943. (b) Nguyen, B. T.; Anslyn, E.
V. Indicator–Displacement Assays. Coord. Chem. Rev. 2006, 250,
12
(
Finally, we successfully applied SWIFT in vapor analysis on a
solid support. To this end, three bands of III were deposited on a
TLC plate and co-spotted with 1a, 3 and 5, respectively. When the
plate was placed in a vial containing a thiol-absorbed cotton plug,
the fluorescence changes due to the corresponding reactions with
PhSH were observed within several minutes under either UV or
visible LED irradiation (Figure 6).
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118–3127.
0
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(
6) Chen, S.; Yu, Y.-L.; Wang, J.-H. Inner filter effect-based
fluorescent sensing systems: a review. Anal. Chim. Acta 2018,
999, 13–26.
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8) Kubista, M.; Sjoback, R.; Eriksson, S.; Albinsson, B.
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5907–15946.
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labeling technologies), 11th ed.; chapter 2 Thiol-reactive probes,
Thermo Fisher Scientific, 2010.
(
12) See Supporting Information for the experimental details.
(13) Rezende, M. C.; Ponce, I.; Oס
ate, R.; Almodovar, I.; Aliaga C.
Change of mechanism with a change of substituents for a Zincke
reaction. Tetrahedron Lett. 2014, 55, 3097–3099.
Figure 6. Thiol detection in gas phase. The detection is
performed with either UV or blue LED excitation.
(
14) Coe, B. J.; Harris, J. A.; Asselberghs, I.; Wostyn, K.; Clays, K.;
Persoons, A.; Brunschwig, B. S.; Coles, S. J.; Gelbrich, T.; Light,
M. E.; Hursthouse, M. B.; Nakatani, K. Quadratic optical
nonlinearities of N-methyl and N-aryl pyridinium salts. Adv.
Funct. Mater. 2003, 13, 347-357.
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nonprotein sulfhydryl groups in tissue with Ellman’s reagent.
Anal. Biochem. 1968, 25, 192–205.
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glutathione using a latent rhodamine. Org. Lett. 2008, 10, 837–
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17) Lee, M. H.; Han, J. H.; Kwon, P.-S.; Bhuniya, S.; Kim, J. Y.;
Sessler, J. L.; Kang, C.; Kim, J. S. Hepatocyte-targeting single
galactose-appended naphthalimide: a tool for intracellular thiol
imaging in vivo. J. Am. Chem. Soc. 2012, 134, 1316–1322.
18) Lee, J. H.; Lim, C. S.; Tian, Y. S.; Han, J. H.; Cho, B. R. A two-
photon fluorescent probe for thiols in live cells and tissues. J. Am.
Chem. Soc. 2010, 132, 1216–1217.
In summary, we presented a new technique (SWIFT) for
designing of fluorescent probes based on analyte-triggered
appearance or disappearance of a short wavelength absorber that
strongly affects the fluorescence of common organic fluorophores
when their excitation is performed near the absorber’s maximum.
The viability of the new method was confirmed by rapid and
selective detection of several important analytes (thiols, fluoride,
hydrogen peroxide). Further studies toward applications of
SWIFT in chemosensing are presently underway.
(
(
(
ASSOCIATED CONTENT
(
(
Supporting Information
The Supporting Information is available free of charge on the
ACS
Publications
website.
Experimental
procedures,
19) Mir, R.; Dudding, T. Phase-transfer catalyzed O ‑ silyl ether
deprotection mediated by a cyclopropenium cation. J. Org. Chem.
characterization data and spectroscopic data (PDF)
2
017, 82, 709−714.
AUTHOR INFORMATION
(20) Zhou, Y.; Zhang, J. F.; Yoon, J. Fluorescence and colorimetric
chemosensors for fluoride-ion detection. Chem. Rev. 2014, 114,
5511−5571.
Corresponding Author
(
21) Cametti, M.; Rissanen, K. Highlights on contemporary
recognition and sensing of fluoride anion in solution and in the
solid state. Chem. Soc. Rev. 2013, 42, 2016−2038.
Notes
(22) Han, J.; Zhang, J.; Gao, M.; Hao, H.; Xu, X. Recent advances in
chromo-fluorogenic probes for fluoride detection. Dyes Pigm.
The authors declare no competing financial interests.
2
019, 162, 412–439.
ACKNOWLEDGMENT
(23) Sokkalingam, P.; Lee, C.-H. Highly sensitive fluorescence “Turn-
On” indicator for fluoride anion with remarkable selectivity in
organic and aqueous media. J. Org. Chem. 2011, 76, 3820–3828.
(24) Nosaka Y.; Nosaka A. Y. Generation and detection of reactive
oxygen species in photocatalysis. Chem. Rev. 2017, 117, 11302–
Financial support was provided by the Israel Science Foundation
ISF) (Grant 669/16) and PAZY Foundation. The authors thank
(
Prof. Doron Shabat (TAU) for valuable discussions.
1
1336.
(25) Herman, J.; Zhang, Y.; Castranova, V.; Neal, S. L. Emerging
technologies for optical spectral detection of reactive oxygen
species. Anal. Bioanal. Chem. 2018, 410, 6079–6095.
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