A new BODIPY-based fluorescent “turn-on” probe for highly selective and rapid detection of mercury ions

Article abstract of DOI:10.1016/j.tetlet.2018.10.068

A new fluorescent sensor based on the BODIPY fluorophore and the carboxyl-thiol metal bonding receptor for Hg²⁺ was designed and synthesized. The sensor is highly selective for Hg²⁺ (about 630-fold fluorescence enhancement) over relevant competing metal ions, sensitive to ppb levels of Hg²⁺ (with detection limit of 5.7 nM), and fast response toward Hg²⁺ (within 30 s) in aqueous solution.

Full text of DOI:10.1016/j.tetlet.2018.10.068

Accepted Manuscript
A New BODIPY-Based Fluorescent “Turn-On” Probe for Highly Selective and
Rapid Detection of Mercury Ions
Baocheng Zhou, Siyao Qin, Bo Chen, Yifeng Han
PII:
S0040-4039(18)31299-1
https://doi.org/10.1016/j.tetlet.2018.10.068
TETL 50378
DOI:
Reference:
Tetrahedron Letters
To appear in:
Received Date:
Revised Date:
Accepted Date:
10 August 2018
26 October 2018
29 October 2018
Please cite this article as: Zhou, B., Qin, S., Chen, B., Han, Y., A New BODIPY-Based Fluorescent “Turn-On”
Probe for Highly Selective and Rapid Detection of Mercury Ions, Tetrahedron Letters (2018), doi: https://doi.org/
10.1016/j.tetlet.2018.10.068
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A New BODIPY-Based Fluorescent “Turn-On” Probe
for Highly Selective and Rapid Detection of Mercury
Ions
Leave this area blank for abstract info.
Baocheng Zhou,* Siyao Qin, Bo Chen, and Yifeng Han*
Tetrahedron Letters
journal homepage: www.elsevier.com
A New BODIPY-Based Fluorescent “Turn-On” Probe for Highly Selective and Rapid
Detection of Mercury Ions
Baocheng Zhou,* Siyao Qin, Bo Chen, and Yifeng Han*
Department of Chemistry, Engineering Research Center for Eco-Dyeing & Finishing of Textiles, Ministry of Education, Zhejiang Sci-Tech University,
Hangzhou, 310018, China.
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
A new fluorescent sensor based on the BODIPY fluorophore and the carboxyl-thiol metal
bonding receptor for Hg2+ was designed and synthesized. The sensor is highly selective for Hg2+
(about 630-fold fluorescence enhancement) over relevant competing metal ions, sensitive to ppb
levels of Hg2+ (with detection limit of 5.7 nM), and fast response toward Hg2+ (within 30
seconds) in aqueous solution.
Available online
2009 Elsevier Ltd. All rights reserved.
Keywords:
Fluorescent probe
Bonding receptor
Turn-on response
Mercury ions
BODIPY
1. Introduction
Mercury, widely distributed in air, soil and water, is one of the
most ubiquitous and poisonous heavy metals.1 Mercury ions are not
biodegradable and hence could be accumulated in human bodies
through the food chain by consumption of fish and marine
mammals.2 In particular, children are easily affected by even low

concentrations of mercury exposure during the early stages of development, and result in a wide variety of diseases related to the
kidneys, brain, and central nervous system.3 Therefore, the monitoring of mercury in environmental and biological samples is crucial
both to the determination of environmental pollution and to the diagnosis of clinical disorders.
In general, traditional analytical methods used for quantification of mercury species, such as anodic stripping voltammetry,4
inductively coupled plasma mass spectrometry,5 atomic absorption-emission spectrometry,6 and reversed-phase high-performance liquid
chromatography,7 often require sophisticated and expensive instrumentation, or sample preparation, and are therefore not convenient for
real-time analysis. However, fluorescence based probes are getting more and more popular in the analytical field for their ease of
application in solution, good cell membrane permeability, as well as their high sensitivity and selectivity to trace analytes with spatial
and temporal resolution.8
Therefore, over the past several years, considerable efforts have been made to develop fluorescent sensors for the detection of
mercury ions based on the Hg2+ catalyzed devinylation reactions,9 Hg2+ catalyzed desulfurization reactions (including hydrolysis,
cyclizations, and eliminations, etc.),10 and the coordination of Hg2+ to heteroatom-based ligands11 (Fig. 1).
Figure 1. Some reported Hg2+ probes.
Although these reported fluorescent Hg2+ probes are highly selective, many of them still have limitations such as high detection
limits, low sensitivity, long response time and laborious synthesis processes with expensive chemicals.12 For example, the
desulfurization reaction-based mercury probes usually suffer from unsatisfied specificity, especially in the discrimination between Hg2+,
Ag+ and/or Cu2+ ions. While, the devinylation reaction-based probes usually exhibit excellent detection selectivity, but tend to have a
relatively slow response time (about 10 min). Thus, the development of a simple yet highly sensitive, and fast response fluorescent
probe for the real time detection of Hg2+ is still in high demand.
Herein, we present the synthesis and properties of a new Hg2+-ion specific fluorescent chemosensor Mercurysensor-5 (MS5) that has
visible wavelength excitation and emission profiles, excellent selectivity for Hg2+ ions over relevant competing metal ions, about 630-
fold fluorescent turn-on response, and high sensitivity to ppb levels of Hg2+ in aqueous solution.
Scheme 1. Fluorescence turn-on sensing of Hg2+ by MS5.
Our design for MS5 combines the boron-dipyrromethene
(BODIPY) fluorophore with the carboxyl-thiol metal bonding
receptor to coordinate to the Hg2+ cations (Scheme 1). The MS5
alone should be non-fluorescence due to the typical photoinduced
electron transfer (PeT) process between BODIPY fluorophore and
the electron donating nitrogen atom from carboxyl-thiol metal
bonding receptor.11d, 13 After binding metal ions, this PeT pathway could be efficiently prohibited, which will result in a remarkable
fluorescence-enhanced response.
2. Results and discussions
As shown in Scheme 2, MS5 can be readily prepared under facile conditions with high yield starting with commercially available 4-
chloronitrobenzene and phthalimide. The product (MS5) was
characterized by 1H, 13C NMR, MS, and HRMS (ESI†).
Scheme 2. Synthesis of MS5: (a) diethanolamine, reflux, 4 h, 48%;
(b) TsCl, Et3N, DCM, r.t., 12 h, 82%; (c) methyl thioglycolate,
K2CO3, acetone, 60 °C, 24 h, 95%; (d) SnCl2, MeCN-EtOH 1:1,
reflux, 12 h, 51%; (e) LiOH, THF-MeOH 1:1.25, r.t., 12 h, quantitative; (f) Et3N, DCM, r.t., 12 h, 48%.
With MS5 in hand, we firstly assessed the UV-vis and fluorescent spectroscopic properties of MS5 in PBS buffer solution (10 mM,
pH 7.4, containing 50% EtOH) (Fig. 2 and 3). As expected, MS5 alone shows a visible absorption band centered at 512 nm (Fig. 2) and
is almost nonfluorescent (λem = 581 nm, Φ = 0.002, Table S1, ESI†), indicative of efficient PeT process quenching of the excited
benzoBODIPY fluorophore by the electron donating nitrogen atom from carboxyl-thiol metal bonding receptor. However, upon
progressive addition of Hg2+ (0-150.0 equiv.), an emission band centered at 581 nm rapidly increased (with a marked color change from
dark to orange, see Fig. 3), which was deduced to be attributed to the prohibited of PeT quenching pathway between BODIPY and
carboxyl-thiol metal bonding receptor by the formation of MS5-Hg2+ complex (Fig. 3 and Scheme 1). On the other hand, in the UV-vis

titration experiment, no obvious change was observed when MS5 is treated
with 100.0 equiv. of Hg2+ (Fig. 2), which is in agreement with the proposed
PeT
mechanis
m.13
Figure 2.
UV-vis
absorbance
spectra of
MS5 (2.5
μM)
in
PBS buffer
solution
(10 mM, pH 7.4, containing 50% EtOH) in the presence of 100.0
equiv. of Hg2+.
Figure 3. Fluorescence spectra of MS5 (2.5 μM) in PBS buffer
solution (10 mM, pH 7.4, containing 50% EtOH) in the presence of
different concentrations of Hg2+ (0-150.0 equiv.). (λex = 540 nm).
Inset 1: The fluorescence intensity of MS5 at 581 nm as a function of Hg2+ concentration (0-150.0 equiv.). Inset 2: Cuvette images of
probe MS5 before and after addition of Hg2+ taken under a hand-held UV-lamp (λex = 365 nm).
Moreover, the fluorescence titration curve revealed that the fluorescence intensity of MS5 at 581 nm increased linearly with
increasing concentration of Hg2+ (Fig. 2) and further smoothly increased until a maximum was reached up to 100.0 equiv. of Hg2+
(about a 630-fold fluorescence enhancement, Φ = 0.121, Table S1, ESI†).
Titration of MS5 with Hg2+ was also followed by fluorescence to determine the MS5/Hg2+ binding ratio and binding constant (Ks).14
Ks of MS5/Hg2+ was determined to be 1.16 × 104 by the nonlinear
least-squares analysis (Fig. S1), which implied the formation of a
complex with 1:1 stoichiometry of MS5 and Hg2+. Moreover, a
Job’s plot experiment, which exhibits a maximum at 0.5 M fraction
of Hg2+, further indicating that a 1:1 MS5/Hg2+ complex is formed
(Fig. 4).15 Accordingly, the structure of MS5/Hg2+ complex is
proposed as shown in scheme 1.
Figure 4. Job’s plot showing the 1:1 binding of MS5 with Hg2+.
The total concentration of the probe and Hg2+ is 50.0 μM in PBS
buffer solution (10 mM, pH 7.4, containing 50% EtOH).
Figure 5. Time-dependent fluorescence intensity changes of MS5
(2.5 μM) upon addition of different concentration of Hg2+ (0, 10,
and 100.0 equiv., respectively) in PBS buffer solutions (10 mM, pH
7.4, containing 50% EtOH) (λex = 540 nm).
Subsequently, the time-dependence of MS5 fluorescence was
evaluated in the presence of Hg2+ in PBS buffer solutions (10 mM,
pH 7.4, containing 50% EtOH). As shown in Fig. 5, no changes in
fluorescence were detected before the addition of Hg2+ to the 2.5 μM solution of MS5. Further, after the addition of 100.0 equiv. of
Hg2+ to the tested solution, the fluorescent intensity at 581 nm remarkably increased to its maximum value within 30 second, which
indicated that MS5 possesses a real-time capability to the detection of Hg2+ ions.
Continuing on, the fluorescence titration of MS5 with various metal ions was conducted to examine its selectivity (Fig. 6 and Fig. S2,
ESI†). Much to our delight, the turn-on response of MS5 is highly specific for Hg2+, and no obvious change in fluorescent response was
observed when it was treated with K+, Cs+, Ca2+, Mn2+, Cu2+, Ni2+, Pb2+, Na+, Zn2+, Cd2+, Sn4+, Fe2+, Co2+, Mg2+, Al3+, and Fe3+. It should
be mentioned that Ag+ ions exhibit a very slight fluorescence response to MS5 (see Fig. 6) due to the high biding affinity of Ag+ ions to
sulfur-containing ligands. However, addition of NaCl to the tested
solution is the simple but useful method to distinguish Hg2+ from
Ag+ because of the high binding affinity between Ag+ and Cl-
(AgCl, Ksp = 1.8 × 10-10).12c On the other hand, MS5 still responds
to Hg2+ sensitively even in the presence of other relevant competing
ions (Fig. 6 and Fig. S3, ESI†).
Figure 6. Fluorescence responses of MS5 to various metal ions
(including K+, Cs+, Ag+, Ca2+, Mn2+, Cu2+, Ni2+, Pb2+, Na+, Zn2+,
Cd2+, Sn4+, Fe2+, Co2+, Mg2+, Al3+, Fe3+, and Hg2+). Black bars
represent the addition of 100.0 equiv. of the appropriate metal ions
to a 2.5 μM solution of MS5 (in PBS buffer solution, 10 mM, pH
7.4, containing 50% EtOH). Red bars represent the addition of

100.0 equiv. of Hg2+ to the solutions containing MS5 (2.5 μM) and the appropriate metal ions (100.0 equiv.) (λex = 540 nm).
Moreover, the Hg2+-sensing ability of MS5 in a wide range of pH values was also investigated. As depicted in Fig. S4, MS5 alone
was inert to pH in the range of 4.5-10.5. On the other hand, it still responded to Hg2+ sensitively within this pH range (4.5-9.1). These
results indicate that MS5 could be used in neutral natural systems, or a mildly acidic or basic environment.
For practical purposes, the detection limit of MS5 for the detection of Hg2+ was also an important parameter. The fluorescence
titration curve revealed that the fluorescence intensity of MS5 at 581 nm increased linearly with the amount of Hg2+ in the 0-50.0 μM
range (R2 = 0.99) (Fig. S5, ESI†). Thus, the detection limit of MS5 for Hg2+ was calculated to be 5.70 × 10-9 M (Hg2+ content = 1.2
ppb), which was below the US Environmental Protection Agency (EPA) threshold in safe drinking water (2.0 ppb).16 These results
showed that MS5 could be a sensitive fluorescent probe for the quantitative detection of Hg2+.
To further investigate the practical application of MS5, we prepared test strips by immersing filter paper into the water solution of
MS5 (1.0 mM) and then dried in air. When dipped into the solutions of Hg2+ ions with different concentrations, the test strips containing
MS5 demonstrated apparent orange-fluorescence excited at 365 nm under a UV lamp, and the discernible concentration of Hg2+ ions
could be as low as 10 μM (Fig. S7, ESI†). Thus, these strips could be conveniently handled at any moment for the detection of Hg2+
ions.
3. Conclusions
In conclusion, we have rationally developed a benzoBODIPY-based sensitive fluorescence probe, MS5, for the detection of Hg2+ in
neutral aqueous solution via PeT mechanism. The probe has the unique advantages of excellent selectivity and sensitivity, and fast
response towards Hg2+, with a low detection limit (5.7 nM). We anticipate that the experimental results of this study will inspire the
future designing of heavy metal ion sensors for a variety of chemical and biological applications.
Acknowledgments
This work was supported by Zhejiang Provincial Natural Science Foundation of China (Grant No. LY17B070008), Science
Foundation of Zhejiang Sci-Tech University (Grant No. 15062174-Y), and the Project Grants 521 Talents Cultivation of Zhejiang Sci-
Tech University.
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Supplementary Material
Supplementary data (additional spectroscopic of MS5) associated with this article - copies of 1H and 13C NMR Spectra can be found,
in the online version, at http://dx.doi.org.
Click here to remove instruction text...
Highlights
1. A new BODIPY-based fluorescent sensor for Hg2+ has been designed and synthesized.
2. The probe is highly selective for Hg2+ over relevant competing metal ions.
3. The probe features rapid detection kinetics (< 30 sec.).