Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148 (2015) 7884

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Spectrochimica Acta Part A: Molecular and

Biomolecular Spectroscopy
journal homepage: www.elsevier.com/locate/saa

A colorimetric and absorption ratiometric anion sensor based on indole

& hydrazide binding units
Linbo Zou, Boren Yan, Dingwu Pan, Zan Tan, Xiaoping Bao
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of
Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, Peoples Republic of China

g r a p h i c a l a b s t r a c t

 An effective anion sensor L bearing

0.40

0.6

0.35
0.30

0.5

0.25
0.20
0.15

Absorbance

indole & hydrazide units was

synthesized.
 Sensor L displayed the colorimetric
and absorption ratiometric responses
towards F, AcO and H2PO4 in
DMSO.
 Sensor L underwent NH
deprotonation event upon addition of
excessive F in DMSO-d6.

A 456 /A 298

h i g h l i g h t s

0.4

0.10
0.05
0.00

0.3

10

20

30
_

40

50

60

[F ](M)

0.2
0.1
0.0
300

400

500

600

Wavelength(nm)

a r t i c l e

i n f o

Article history:
Received 29 November 2014
Received in revised form 13 March 2015
Accepted 27 March 2015
Available online 3 April 2015
Keywords:
Colorimetric sensor
Absorption ratiometry
Indole
Hydrazide NH

a b s t r a c t
A colorimetric and absorption ratiometric anion sensor (L) based on indole and hydrazide binding units
was designed and synthesized, and its recognition & sensing properties towards different anions were
studied by naked-eye observations, UVvis and 1H NMR titration spectra. Sensor L could selectively
recognize biologically important F, AcO and H2PO
4 in DMSO over other anions, along with a signicant
change in its color and absorption spectrum, resulting from the formation of corresponding 1:2 (L/F) and
1
1:1 (L/AcO and L/H2PO
4 ) complexes. The H NMR titration experiments proved that sensor L experienced deprotonation of NH fragment and produced [HF2] species, whereas a stable H-bonding complex
was formed in the presence of AcO and H2PO
4.
2015 Elsevier B.V. All rights reserved.

Introduction
More and more attention has been focused on the development
of anion receptors or sensors due to key roles of anions in many
chemical and biological processes [15]. Among common anions,
uoride, acetate and dihydrogenphosphate ions received the most
concerns because of their special physiological & biochemical functions in the human body. For example, uoride was proved to be
associated with dental care, osteoporosis and environmental
pollution [6]. Acetate ion in the human protein components
works as a molecular switch in diverse cellular processes,
Corresponding author. Tel.: +86 851 8292170; fax: +86 851 3622211.
E-mail address: baoxp_1980@aliyun.com (X. Bao).
http://dx.doi.org/10.1016/j.saa.2015.03.109
1386-1425/ 2015 Elsevier B.V. All rights reserved.

such as cell division, DNA inheritance and cell aging [7].

Dihydrogenphosphate and its analogues play key roles in signal
transduction and energy storage of biological system [8].
Compared with uorescent and electrochemical sensors, colorimetric sensors had some obvious advantages, such as its convenience, low cost and good visualization [9]. On the other hand,
ratiometric sensors could provide more reliable quantitative information since they utilized the ratio of absorption/emission intensity at two different wavelengths as a function of analyte
concentration, relative to conventional sensors only depending
on a single wavelength for quantitative analysis [1012].
Most of colorimetric anion sensors were composed of two parts,
that is, binding unit and chromophore unit. The extensively-used
binding units include amide, urea, thiourea, pyrrole, indole and

L. Zou et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148 (2015) 7884

sulfonamide. And recently, a few anion sensors based on hydrazide

NH unit were reported, which displayed remarkable differences in
their recognition behaviors in spite of small variations in their
chemical structures (having nearly the same binding unit and
chromophore moiety for these sensors). For example, Shi et al.
[13] reported diacylhydrazine-based colorimetric receptors for
selective sensing of F and AcO (from colorless to yellow) over
other anions (including H2PO
4 ) in acetonitrile solution, with the
formation of a 1:1 stoichiometric complex between the receptors
and the anions. Chen and co-workers [14] developed an
organogelator containing a hydrazide unit, and its chloroform gel
was transferred into a red solution after treatment with F, AcO
and H2PO
4 , due to the disruption of intermolecular H-bonding
interactions among receptor molecules via deprotonation of hydrazide NH. Trivedi et al. [15] synthesized a benzohydrazide-based
anion receptor with one p-nitrophenyl chromophore, which
demonstrated obvious color and spectral changes in DMSO solution only in the presence of F and AcO (excluding H2PO
4 ). Very
recently, Bai and co-workers [16] prepared a p-nitrobenzohydrazide derivative and it formed 1:1 H-bonded complexes

with AcO and H2PO
4 in DMSO. For F , an initial H-bonding interaction was followed by deprotonation of NH. The addition of F,
AcO and H2PO
4 into DMSO solution of the receptor induced a
remarkable color change from colorless to red. To our best knowledge, there was no example of integrating hydrazide NH and other
NH units into a single anion receptor, which afforded colorimetric
& absorption ratiometric responses upon addition of anions.
Herein, we developed an effective anion sensor L (Scheme 1) with
indole & hydrazide NHs as binding units and p-nitrobenzene moiety
as a chromophore. Different with the previously reported hydrazide-based anion sensors [1316], L demonstrated a good selectivity
towards F (1:2 complex), AcO and H2PO
4 (1:1 complex) over other
anions in DMSO, along with a marked color change and absorption
ratiometric responses during the recognition process.
Experimental
General
All chemicals were purchased from commercial suppliers and
used without further purication. Dry CH2Cl2 and TEA were
obtained by reuxing over CaH2 and distillation before use. All
the anions were used as their tetra-n-butylammonium salts.
Melting points were determined on a XT-4 binocular microscope
(Beijing Tech Instrument Co., China). IR spectra were recorded on
a Shimadzu IR Prestige-21 spectrometer in KBr disk. 1H and 13C
NMR spectra were measured on a JEOL-ECX 500 NMR spectrometer
at room temperature using TMS as an internal standard. Mass
spectra were recorded on an Agilent LC/MSD Trap VL. Elemental
analysis was performed on an Elementar Vario-III CHN analyzer.
UVvis spectra were recorded on a TU-1900 spectrophotometer
(Beijing Pgeneral Instrument Co., China).
Synthesis of sensor L
Indole-2-acylhydrazine [17] (100 mg, 0.57 mmol) and
p-nitrobenzoyl chloride (106 mg, 0.57 mmol) were dissolved in
dry CH2Cl2 (8 mL) in the presence of dry TEA (0.25 mL), and the
O

resulting mixture was stirred at room temperature for 18 h. The

formed precipitate was ltered off and washed with water, giving
L as a light-yellow solid in 76% yield (140 mg). Mp > 250 C. 1H
NMR (500 MHz, DMSO-d6): d 11.76 (s, 1H, H1), 10.91 (s, 1H, H2),
10.65 (s, 1H, H3), 8.39 (d, J = 9.0 Hz, 2H, H4), 8.17 (d, J = 9.0 Hz,
2H, H5), 7.67 (d, J = 8.70 Hz, 1H, H6), 7.46 (d, J = 8.30 Hz, 1H, H7),
7.29 (s, 1H, H8), 7.23 (t, J = 8.20 Hz, 1H, H9), 7.08 (t, J = 7.50 Hz,
1H, H10); 13C NMR (125 MHz, DMSO-d6): d 164.6, 160.9, 149.6,
138.2, 136.8, 129.5, 129.2, 127.1, 124.0, 121.9, 120.1, 112.6,
103.8; IR (KBr, cm1): 3323 (NAH), 1633 (C@O), 1524 (NO2),
1346 (NO2); MS-ESI: 323.1 ([MH]); Anal. Calcd for
C16H12N4O4: C, 59.26; H, 3.73; N, 17.28. Found: C, 59.13; H, 3.89;
N, 17.55.
UVvis and 1H NMR titration experiments
Stock solution of sensor L being studied was prepared in DMSO
with the nal concentration of 20 lM. To a 3.0 mL of the above
solution was added DMSO solution of each anion (15 mM) using
a Hamilton syringe. After each of addition, the UVvis spectrum
was recorded. All the titration experiments were carried out on a
Pgeneral TU-1900 spectrometer at 298 K.
To a 0.5 mL of DMSO-d6 solution of L (3.0 mM) was added
DMSO-d6 solution of each anion (60 mM). After each of addition,
the 1H NMR spectrum was measured.
Results and discussion
UVvis studies
Initially, sensor L was examined for its colorimetric sensing
capabilities in DMSO upon addition of different anions. As shown
in Fig. 1, a signicant color change from colorless to yellow was
observed in the presence of F, AcO and H2PO
4 . In contrast, no
perceptible color change happened after addition of other anions,



such as Cl, Br, I, ClO
4 , N3 , NO3 and HSO4 . Subsequently, the
selectivity of L for various anions was further conrmed by UV
vis spectroscopy. From Fig. 2, addition of F, AcO or H2PO
4 anions
to L induced the appearance of a new absorption peak around
456 nm (responsible for the vivid color change), concomitant with
an evident decrease in the original peak at 296 nm. Upon treatment with other seven anions, very slight or no spectral change
was found for L.
Encouraged by the above phenomena, the binding interactions
of sensor L with F, AcO and H2PO
4 were investigated in detail
through UVvis titration spectra. As shown in Fig. 3, upon addition
of increasing amounts of F to DMSO solution of L, the absorbance
at 296 nm was gradually decreased and a new absorption peak at
456 nm progressively evolved. A distinct isosbestic point was
detected at 312 nm, indicating that only two absorbing species
coexisted in the titration mixture [18]. The plot of 1/(AA0) displayed an excellent linear relationship with 1/[F]2 according to
the BenesiHildebrand equation (Fig. 4), proving that L bound
F in a 1:2 stoichiometry with a binding constant of (1.15
0.15)  109 M2.
Signicantly, there was a good linear relationship between the
ratio of the absorbance (A456/A296) in sensor L and the concentration of F ranging from 0 to 55 lM, therefore allowing quantitative

COCl

NHNH2

N
H1

dry CH 2Cl2
N
H

79

Et3N, r.t., 18 h

10

O
O

NO 2

Scheme 1. Synthesis of sensor L.

HN NH
2

5
4

NO 2

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L. Zou et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148 (2015) 7884


 



Fig. 1. Color changes of sensor L (50 lM) in DMSO upon addition of 8.0 equiv of different anions (from left to right: free L, F, AcO, H2PO
4 , Cl , Br , I , HSO4 , NO3 , N3 and
ClO
4 ). (For interpretation of the references to color in this gure legend, the reader is referred to the web version of this article.)

1.2

30

1.0

25

20

1/(A-A0)

Absorbance

0.8

0.6
_

+F

+AcO
_
+H2PO4

0.4

0.2

y=51.5231*x+5.9353
r=0.9965

Sensor L, +Cl , +Br ,

+I , +NO3 , +ClO4 ,
-

15

10

+N3 ,+HSO4

0.0
300

400

500

600

700

Wavelength(nm)

0.0

0.1

0.2

0.3
_ 2

Fig. 2. UVvis changes of sensor L (50 lM) in DMSO upon addition of 8.0 equiv of
different anions.

0.4

0.5

10

1/[F ]

(10 )

Fig. 4. BenesiHildebrand plot (k = 456 nm) of sensor L and F.

0.40

0.6

0.35

0.5

0.4

A456/A296

Absorbance

0.30

0.3

0.25
0.20
0.15

0.2

y=0.00707*x+0.00498
r=0.9935

0.10
0.05

0.1

0.00

0.0
300

400

500

600

Wavelength(nm)
Fig. 3. UVvis spectral changes of sensor L (20 lM) in DMSO upon addition of 0
9.25 equiv of F.

detection of F by absorption ratiometric method (Fig. 5). The

detection limit (LOD) of L for F was calculated to be 6.3 lM,
through the formula (LOD = 3r/k, r and k represent standard
deviation and slope of linear regression curve, respectively) [19].
Similar spectral changes were observed when addition of AcO
or H2PO
4 to DMSO solution of L. However, the best tting of

10

20

30

40

50

60

[F ] ( M)
Fig. 5. Plot of the absorbance ratio at 456 and 296 nm (A456/A296) as a function of F
concentration.

titration isotherm was achieved on assuming the formation of a

1:1 complex between L and these two anions (Fig. 6 and 7),
giving the binding constant of (3.44 0.40)  104 M1 and
(7.38 0.38)  103 M1 for AcO and H2PO
respectively.
4,
Furthermore, the detection limit of sensor L for AcO and H2PO
4
was 12.0 and 18.7 lM (Fig. 8 and 9), respectively.

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L. Zou et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148 (2015) 7884

0.5

Absorbance

0.4

0.3

0.18
0.16
0.14
0.12
0.10
0.08
0.06
0.04
0.02
0.00

0.25

0.20

Equiv of AcO

10

A456/A296

Abs at 456 nm

0.6

12

0.15

y=0.00138*x+0.02737
r=0.9941

0.10

0.2
0.05

0.1
0.00

0.0
300

400

500

600

-20

700

20

40

60

100

120

140

160

180

Wavelength(nm)
Fig. 6. UVvis spectral changes of sensor L (20 lM) in DMSO upon addition of 0
11.0 equiv of AcO. The inset was non-linear curve tting of the absorbance at
456 nm against the added AcO according to a 1:1 binding ratio.

80

[H2PO4 ] ( M)
Fig. 9. Plot of the absorbance ratio at 456 and 296 nm (A456/A296) of L as a function
of H2PO4 concentration.

Determination of association constants (Ka)

0.6

Abs at 456 nm

0.5

0.4

Absorbance

When assuming a 1:2 binding stoichiometry between L and F,

the binding constant (Ka) could be determined by the Benesi
Hildebrand equation [20,21] as follows:

0.14

0.3

0.12
0.10

"
#
1
1
1

1
A  A0 A1  A0 K a F 20

0.08
0.06
0.04
0.02
0.00

0.2

10

15

Equiv of H 2PO 4

20

25

0.1

0.0
300

400

500

600

700

Wavelength(nm)
Fig. 7. UVvis spectral changes of sensor L (20 lM) in DMSO upon addition of 0
22.5 equiv of H2PO
4 . The inset was non-linear curve tting of the absorbance at
456 nm against the added H2PO
4 according to a 1:1 binding ratio.

0.40
0.35
0.30

A456/A296

0.25
0.20

y=0.00449*x+0.04788
r=0.9907

0.15

A0 is the absorbance of L without F, A is the absorbance of L after

treatment of F, A1 is the absorbance of L upon addition of excessive F, [F]0 is the concentration of added F. A good linear
relationship was obtained by plotting 1/(A  A0) against 1/[F]2
(as shown in Fig. 4), indicating the formation of 1:2 (L/F) complex.
The binding constant (Ka) was determined from the ratio of intercept/slope.
In a supramolecular system with the formation of 1:1 binding
complex, the binding constant can be calculated using the following equation [22]:

h
i1=2 
2
A A0 Alim  X 0 =2C 0 C H C G 1=K a  C H C G 1=K a  4C H C G

where A is the absorbance of the whole system; A0 is the absorbance

of free receptor; CH and CG are the corresponding concentration of
receptor compound and guest anion; Ka is the binding constant.
The binding constants and correlation coefcients (R) were
obtained from the nonlinear curve tting of A versus CG/CH. The
obtained correlation coefcients (R = 0.9950 and 0.9987 for AcO
and H2PO
4 , respectively) were both larger than 0.99, proving the
formation of 1:1 binding complex between L and AcO/H2PO
4
[2328].
The spectrometric data were processed based on the Benesi
Hildebrand equation and nonlinear curve tting method for 1:2
(L/F) and 1:1 (L/AcO and L/H2PO
4 ) binding models, respectively,
by using the Origin 6.0 program.

0.10
1

H NMR titration studies

0.05
0.00
0

20

40

60

80

[AcO ] ( M)
Fig. 8. Plot of the absorbance ratio at 456 and 296 nm (A456/A296) of L as a function
of AcO concentration.

To disclose the nature of interactions between sensor L and

anions, 1H NMR titration studies were carried out in DMSO-d6.
The chemical shift changes of L upon addition of 1.0 equiv of different anions were displayed in Fig. 10, from which we could nd: (1)
Only the presence of F, AcO and H2PO
4 caused an obvious
change in the chemical shifts of NH and aromatic CH protons,

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L. Zou et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148 (2015) 7884

Fig. 10. Partial 1H NMR spectra of L (3.0 mM in DMSO-d6) upon addition of 1.0 equiv of various anions.

Fig. 11. Partial 1H NMR spectra of L (3.0 mM) in DMSO-d6 upon addition of different equivalents of F.

showing effective interactions between L and these three anions;



(2) the addition of HSO
4 , NO3 and N3 induced a certain broadening
of hydrazide NH signals and no detectable change for indole NH
and aromatic CH protons was found, indicating very weak interactions between L and these three anions; (3) the addition of Cl, Br,
I and ClO
4 to L did not produce any discernible change in all of the
proton chemical shifts, suggesting no interactions between L and
these four anions. The observed high afnity and selectivity of L
for F, AcO and H2PO
4 over other anions were rationalized
due to the following reasons: (1) Strong competitiveness of
DMSO solvent disfavored the binding of L with these seven
anions; (2) The above three anions had much larger basicities
(namely, better H-bonding accepting capabilities) than those of
the remaining anions.

Subsequently, the binding interactions between L and F, AcO

1
and H2PO
4 were investigated in detail through H NMR titration
spectra. As shown in Fig. 11, addition of 0.48 equiv of F caused
a slight upeld shift (0.03 ppm) for H1, concomitant with the
disappearance of H2 & H3 signals and the appearance of a new
broad signal at d = 10.66 ppm, providing direct evidence for the formation of NAH  F H-bonds [14]. While gradually increasing the
concentration of F up to 2.0 equiv, the signal of hydrazide NH
completely disappeared and indole NH was found to experience
an upeld shift of 0.12 ppm in this circumstance. Interestingly, a
new triplet peak at 16.08 ppm (assigned to HF
2 species [2931])
developed after addition of 3.55 equiv of F, indicative of the
appearance of NH deprotonation in the context of 1H NMR titration
experiments. During the stage of H-bonding interactions ([F]/

L. Zou et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148 (2015) 7884

83

Fig. 12. Partial 1H NMR spectra of L (3.0 mM) in DMSO-d6 upon addition of different equivalents of AcO.

Fig. 13. Partial 1H NMR spectra of L (3.0 mM) in DMSO-d6 upon addition of different equivalents of H2PO
4.

[L] = 02.6), all the aromatic protons underwent an upeld shift to

a different extent, with the most prominent protons for H8 and H4
(0.49 and 0.17 ppm, respectively). Upon addition of AcO, the
chemical shift changes of L (Fig. 12) were similar to those of F,
except for no event of NH deprotonation.
Different with F and AcO, a slight downeld shift of indole NH
signal in L was found while gradually increasing the concentration
of H2PO
4 added (Fig. 13). Moreover, the variation trend of hydrazide NH was the same as that of AcO.

Based on the obtained UVvis and 1H NMR titration results, a

 
possible binding model between L and H2PO
4 /AcO /F in DMSO
was proposed in Scheme 2. The formation of such H-bonding
interactions (or the appearance of NH deprotonation upon
addition of excessive F) modulated electronic properties of the
chromophore, resulting in absorption spectral and color changes
due to a new charge-transfer interaction between anion-bound
amide moiety and the electron-decient p-nitrophenyl
chromophore.

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L. Zou et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148 (2015) 7884
O
N
H

N NH
H
L

N
H
NO2

N N
H H
A

NO 2

+FO
N
H

N
NO 2

H O

A
O

N
H

N
H

N
H

N
H

A = AcO-; H2 PO4 -

+FN
H
NO 2

N
H

N
H

O
N N
H
H O

N
H
NO 2

e
ex

O
N
H

ve
si

F-

NO 2

N N
H

NO 2

F H F

 
Scheme 2. A possible binding model between L and H2PO
4 /AcO /F in DMSO.

Conclusions
In conclusion, we synthesized an effective colorimetric and
absorption ratiometric anion sensor L based on indole and hydrazide NHs. Sensor L displayed a good selectivity for F, AcO and
1
H2PO
4 over other anions, through UVvis and H NMR titration
experiments. 1H NMR titration experiments proved that sensor L
underwent NH deprotonation event upon interaction with excessive F.
Acknowledgements
We gratefully thank the National Natural Science Foundation of
China (No. 21161005) for nancial support.
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