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Supramolecular Chemistry
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A new fluoride ion colorimetric sensor based on

azo–azomethine receptors
a a
Raziyeh Arabahmadi & Saeid Amani
a
Department of Chemistry, Faculty of Sciences , Arak University , Dr. Beheshti Ave, Arak ,
38156-8-8349 , Iran
Published online: 26 Sep 2013.

To cite this article: Raziyeh Arabahmadi & Saeid Amani , Supramolecular Chemistry (2013): A new fluoride ion colorimetric
sensor based on azo–azomethine receptors, Supramolecular Chemistry, DOI: 10.1080/10610278.2013.833334

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 Supramolecular Chemistry, 2013
http://dx.doi.org/10.1080/10610278.2013.833334

A new fluoride ion colorimetric sensor based on azo– azomethine receptors

Raziyeh Arabahmadi and Saeid Amani*
Department of Chemistry, Faculty of Sciences, Arak University, Dr. Beheshti Ave, Arak 38156-8-8349, Iran
(Received 7 April 2013; accepted 6 August 2013)

Four new colorimetric chemosensors, receptors 1a – 1d, containing electron-donating moieties appended to the azophenol
moiety were synthesised. The dyes were characterised by elemental analysis, infrared, UV – vis and nuclear magnetic
resonance (NMR) spectra. Spectral characteristics of the dyes were investigated in four organic solvents of differing polarity
and their chromogenic behaviours towards various anions. The sensors showed a colour change upon addition of fluoride ion
with a substantial bathochromic shift. No significant colour changes was observed upon addition of any other anions.
The significant changes of absorption bands and colour show that chemosensor was selective towards fluoride ion over other
anions such that Cl2, Br2 and NO2 3 could not cause any colour change. The sensing action was further confirmed by
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UV – vis titration. In addition, 1H NMR experiments were carried out to explore the nature of interaction between receptors
and F2.
Keywords: test kit; receptor; colorimetric sensors; solvatochromism; fluoride ion

1. Introduction they also find direct applications in the development of

Anion recognition is an area of growing interest in
supramolecular chemistry due to its important role in a wide
range of environmental, clinical, chemical and biological
applications, and considerable attention has focused on the
design of supramolecular sensors that are able to selectively
recognise and sense anion species (1–12). Among the
biologically important anions, fluoride is of particular
interest due to its established role in dental care and
osteoporosis (13–17). The addition of fluoride in drinking
water and toothpastes has become widespread due to the
valuable effects of fluoride in human health. Molecular
chemistry has developed a wide range of procedures for
creating even more sophisticated molecules and materials
from atoms linked by covalent bonds (18, 11). Beyond
molecular chemistry, supramolecular chemistry aims at
constituting highly complex, functional chemical systems
from components held together by intermolecular forces.
Chemosensors are the molecules of abiotic origin that bind
selectively and reversibly with the analyte. Change in one or
more properties of the system, such as colour (colorimetric
chemosensors) or fluorescence (fluorescent chemosensors)
or redox potentials (electrochemical sensors), is observable
(19–26). Among different types of chemosensors, colori-
metric/chromogenic chemosensors are especially attractive
because the guest determination can be carried out by the
naked eye, without the use of expensive equipment, and
optodes and disposable dipstick arrays based on absorption
changes (27–33). In colorimetric chemosensors, a bath-
ochromic or hypsochromic shift of absorption spectra or
visual colour change is affected by the respective increase
or decrease in electron densities on the chromophore
moiety. So, most of the chromogenic sensors are available
for only charged guests. The term solvatochromism is used
to describe the shift of an UV or visible absorption band in
solvents of different polarities. Dye molecules with
solvatochromic strong character have been used as probes
in the study of micelle/solution interfaces, model liquid
membranes, microemulsions and phospholipid bilayers, as
well as in the dyes applied in analytical chemistry for
indicating solvent polarity. Dependence of absorption
spectra on the solvent polarity refers to the difference in
dipole moment between the ground and excited states of the
chromophore. Variations in the intensity, position and shape
of the absorption spectra can be used to understand the
non-specific and specific interactions between the probe
and solvent molecules (34–36). Here, we report the
synthesis, characterisation and chromogenic studies on
hosts (1a–1d) with azophenol moiety as the end groups
so as to dispose two –OH groups capable of forming
H-bonding or undergoing deprotonation in the presence of
anion. We prepared a set of four hosts 1a–1d based on
azophenol–imine platform, cf. Scheme 1.

*Corresponding author. Email: s-amani@araku.ac.ir

q 2013 Taylor & Francis
 2 R. Arabahmadi and S. Amani

N N

N OH OH N
R3 N N R3

R2 R1 R1 R2
R1 , R2=H R3=(CH2)3CH3 1a
R2=H R1 , R3= CH3 1b

N N N
H
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N OH OH N
R3 N N R3

R2 R1 R1 R2
R1 , R2=H R3=(CH2)3CH3 1c

R2=H R1 , R3= CH3 1d

Scheme 1. Synthesised receptors (1a – 1d).

2. Experimental
2.1 Physical measurements
Determinations of C, N and H composition were
undertaken using an Elemental Analysis System carried
out by GmbH Vario EL III (Germany). Electronic spectra of
receptors in CH3CN/DMSO (dimethylsolfoxide) were
recorded on a Perkin-Elmer Lambda 15 (Germany).
Fourier transform infrared (FTIR) spectra of the com-
pounds as KBr discs were obtained in the 4000 –400 cm21
range with a Galaxy series FTIR 5000 spectrometer
(England). Melting points of all newly prepared compounds
were determined on Electrothermal 9200 apparatus
(Germany). 1H NMR spectroscopy was performed using a
Bruker 300 MHz spectrometer (Germany)
2.2 Materials
All solvents were of reagent grade quality and were purchased
from Merck Chemical Company (Germany) and used as
received without further purification. All anions in the form of
tetrabutylammonium salts were purchased from Fluka
Company (Spain) and used without further purification.
2.3 Synthesis
2.3.1 Synthesis of the starting materials
1-(3-Formyl-4-hydroxyphenylazo)-4-butylbenzene (C1).
A suspension of 4-butylaniline (6.07 g, 40 mmol) in
hydrochloric acid (36 ml) and water (16 ml) was heated to
708C until complete dissolution. The clear solution was
poured into ice water and was diazotised below 58C with
sodium nitrite (2.8 g, 40 mmol) dissolved in water
(10 ml). The cold diazonium solution was added over
the course of 30 min at 08C to a solution of
salicylaldehyde (4.26 ml, 40 mmol) in water (75 ml)
containing sodium hydroxide (1.6 g) and sodium
carbonate (14.8 g). During the addition process, the
solution was vigorously stirred. The product was
collected by vacuum filtration and washed with NaCl
solution (100 ml, 10%). Coupling of the diazonium
reagent to the salicylaldehyde occurred at the position
para to the hydroxyl group. The diazo compound was
recrystallised several times from ethyl alcohol. Yellow,
yield: 92%, m.p.: 86 – 888C. FTIR (KBr, cm21): 3211
( – OH group), 1666 ( – CHO group), 1620 (CvC), 1574
(phenol ring), 1481 (NvN), 1286 (CZO). lmax (nm)
(1 (M21 cm21)): 268 (15,796), 346 (34,292), 445
(13,556) in dimethylformamide (DMF). 1H NMR (d6-
DMSO, 300 MHz, ppm) d: 10.36 (1H, s), 8.15 (1H, s), 8.0
(1H, dd, J ¼ 8.9, 2 Hz), 7.7 (2H, d, J ¼ 8 Hz), 7.4 (2H, d,
J ¼ 8.01 Hz), 7.2 (1H, d, J ¼ 8.8 Hz), 2.6 (2H, t,
J ¼ 7.6 Hz), 1.59 (2H, p, J ¼ 7.05 Hz), 1.3 (2H, q,
J ¼ 7.2 Hz), 0.9 (3H, t, J ¼ 7.1 Hz).
1-(3-Formyl-4-hydroxyphenylazo)-2,4-dimethylbenzene
(C2). Compound C2 was synthesised from 2,4-dimethylani-
line (5.44 g, 40 mmol) following the procedure given above
 Supramolecular Chemistry
for C1, using the same molar ratio of the reagents. The purity
of the compound was evaluated using thin layer
chromatography. Brown, yield: 38%, m.p.: 130–1338C.
FTIR (KBr, cm21): 3014 (–OH group), 1649 (–CHO
group), 1614 (CvC), 1581 (phenol ring), 1481 (NvN),
1278 (CZO). lmax (nm) (1 (M21 cm21)): 268 (19,120), 346
(40,340), 456 (14,292) in DMF. 1H NMR (d6-DMSO,
300 MHz, ppm) d: 11.8 (1H, br), 10.36 (1H, s), 8.1 (1H, s),
8.0 (1H, d, J ¼ 7.9 Hz), 7.5 (1H, d, J ¼ 8.4 Hz), 7.27 (1H, s),
7.23 (1H, s), 7.1 (1H, d, J ¼ 8.3 Hz), 2.7 (3H, s), 2.3 (3H, s).
2.3.2 Synthesis of the Schiff base ligands
A solution of related diamine (1 mmol) in absolute
EtOH (15 ml) was added to a stirring solution of azo-
coupled precursors C1 – C2 (2 mmol) in absolute EtOH
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(60 ml) during a period of 7 min at 70 – 808C. The
mixture was heated in water bath for 4 h at 808C with
stirring. The mixture was filtered and the obtained
solid was washed with hot ethanol. The resultant
product was dried in air.
Synthesis of bis(4-(4-butyl-phenylazo)-phenol)-O-pheny-
lene diimine (1a). Yellow, yield: 87%, m.p.: 2048C. Anal.
calcd for C40H40N6O2·CH3OH, C: 73.59, H: 6.7, N:
12.25. Found: C: 73.76, H: 6.7, N: 12.77%. FTIR (KBr,
cm21): 3329 ( – OH group), 1614 (CvN group), 1585
(CvC), 1570 (phenol ring), 1483 (NvN), 1282 (CZO).
1 3.
H NMR (d6-DMSO, 300 MHz, ppm) d: 13.64 (2H, s),
9.1 (2H, s), 8.3 (2H, s), 7.9 (2H, s), 7.7 (4H, s), 7.5 (2H, s),
7.4 (2H, s), 7.3 (4H, s), 7.1 (2H, s), 2.6 (4H), 1.5 (4H), 1.3
(4H), 0.9 (6H).
Synthesis of bis(4-(2,4-dimethyl-phenylazo)-phenol)-O-
phenylene diimine (1b). Dark brown, yield: 41%, m.p.:
1898C. Anal. calcd for C36H32N6O2, C: 74.4, H: 5.5, N:
14.4. Found: C: 74.21, H: 4.5, N: 14.29%. FTIR (KBr,
cm21): 3014 ( – OH group), 1612 (CvN group), 1587
(CvC), 1575 (phenol ring), 1481 (NvN), 1286 (CZO).
1
H NMR (d6-DMSO, 300 MHz, ppm) d: 13.63 (2H, s),
9.1 (2H, s), 8.3 (2H, s), 7.9 (2H, d, J ¼ 6.5 Hz), 7.5 (2H,
s), 7.4 (4H, s), 7.2 (2H, s), 7.1 (4H, s), 2.6 (6H, s), 2.3
(6H, s).
Table 1. Infrared spectral data of C1 – C2 and 1a – 1d receptors (cm21).
Compounds n(CvO) n(CvC) n(CZO)
C1 1666 1620 1286
C2 1649 1614 1278
1a – 1585 1282
1b – 1587 1286
1c – 1612 1265
1d – 1610 1282
3
Synthesis of bis(4-(4-butyl-phenylazo)-phenol)diethylene
triimine (1c). Yellow, yield: 67%, m.p.: 1248C. Anal. calcd
for C38H45N7O2, C: 72.2, H: 7.12, N: 15.5. Found: C: 71.98,
H: 7.92, N: 15.36%. FTIR (KBr, cm21): 3290 (– OH
group), 1637 (CvN group), 1612 (CvC), 1512 (phenol
ring), 1429 (NvN), 1265 (CZO). 1H NMR (d6-DMSO,
300 MHz, ppm) d: 8.3 (2H, s), 7.9 (1H, s), 7.8 (1H, d,
J ¼ 8.9 Hz), 7.6 (2H, d, J ¼ 7.8 Hz), 7.3 (2H, d,
J ¼ 7.7 Hz), 6.8 (1H, d, J ¼ 9.03 Hz), 3.6 (2H, s), 3.4
(NH, s), 2.9 (2H, s), 2.6 (4H, t, J ¼ 7.2 Hz), 1.5 (4H, t,
J ¼ 6.9 Hz), 1.3 (4H, q, J ¼ 6.7 Hz), 0.9 (6H, t, J ¼ 7 Hz).
Synthesis of bis(4-(2,4-dimethyl-phenylazo)-phenol)
diethylene triimine (1d). Light brown, yield: 31%, m.p.:
1198C. Anal. calcd for C34H37N7O2, C: 71.4, H: 5.89, N:
17.4. Found: C: 70.97, H: 6.43, N: 17.03%. FTIR (KBr,
cm21): 3427 (– OH group), 1633 (CvN group), 1610
(CvC), 1581 (phenol ring), 1489 (NvN), 1282 (CZO).
1
H NMR (d6-DMSO, 300 MHz, ppm) d: 8.32 (2H, s), 8.37
(2H, s), 8.1 (2H, d, J ¼ 9 Hz), 7.9 (2H, s), 7.8 (2H, d,
J ¼ 9.4 Hz), 7.6 (2H, d, J ¼ 8.9 Hz), 6.6 (2H, d,
J ¼ 9.8 Hz), 3.6 (4H, s), 2.9 (4H, s), 3.3 (NH, s), 2.7
(6H, s), 2.2 (6H, s).
Results and discussion
3.1 Infrared spectra
The positions of some of the prominent bands in the
infrared (IR) spectra of C1 – C2 and 1a – 1d receptors are
given in Table 1. A strong band observed in the IR
spectra of C1 and C2 in the region of 1655 – 1675 cm21
can be assigned to the n(CvO) group. The total
absence of the y (CvO) band in the IR spectra of the
prepared dyes together with the appearance of new n
(CvN) band in the range of 1612 – 1637 cm21 clearly
indicated that new Schiff base compounds had formed
in each case. The symmetric NvN stretching mode in
the IR spectra of 1a – 1d leads to a medium band at
1429 – 1489 cm21, while the n(CZO) stretching mode
gives an intense band within the range 1265 –
1286 cm21 (37 – 41).
n(CvN) n(phenol ring) n(NvN)
– 1574 1481
– 1581 1481
1614 1570 1483
1612 1575 1481
1637 1512 1429
1633 1581 1489
 4 R. Arabahmadi and S. Amani
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Figure 1. Partial 1H NMR (300 MHz) spectra of host 1a in DMSO, (A) in the absence, (B) presence of 1.0 equiv. and (C) presence of
2.0 equiv. of TBAF.
1
3.2 H NMR spectra
1
H NMR titration experiments were performed to under-
stand the character of the receptor –anion interactions.
In the 1H NMR spectra of the receptors, the singlet
resonances in the 13.6 ppm regions can be attributed to the
protons of the phenolic OH groups. All three receptors
exhibit singlet signals in the range of 9.1– 8.3 ppm, which
were attributed to imine protons. 1H NMR spectrum was
recorded by treating the receptor with F2 ion. It was found
that the peak at 13.64 ppm corresponding to the proton of
the phenolic OH group disappeared on the addition of
1 equiv. of F2. This demonstrates the interaction of anion
through the phenolic OH group in the receptor (Figure 1).
At the same time, deprotonation of the receptor can be
possibly occurred, and indeed, we observed such
deprotonation and the formation of HF2 1
2 in the H NMR
spectra of 1a as a new signal at ca. 16 ppm (Figure 1C)
(18). Consequently, we propose that the F2 recognition
occurs by the initial hydrogen bonding of the anion to the
receptor, followed by deprotonation that brings electron
density onto the p-conjugated framework through bond
propagation, thus causing a shielding effect and inducing
small upfield shift of aromatic protons.
3.3 Electronic absorption spectra
The UV – vis absorption spectra of the azo-coupled
salicylaldehyde precursors C1 and C2 display mainly two
bands arising from the p ! p * transitions in the
backbone, while the third band at 310 –345 nm is due to
n ! p * transition in the visible region.
The electronic absorption spectrum of the receptors in
the absence of anions showed three transitions in DMSO.
The first band in the wavelength 260 –276 nm was
assigned to the excitation of the p-electrons of the
aromatic system. The second band observed in the
wavelength 360 – 375 nm could be due to p ! p *
transition of azo and azomethine groups. The third band
located in the wavelength of 427– 469 nm is due to an
intramolecular charge transfer transition within the whole
molecule (19, 39, 42).
3.4 Solvatochromism behaviour
It is well known that the UV – vis absorption spectra
(positions, intensities and shapes) of azo – azomethine
ligands are usually influenced by the surrounding medium
and solvents (42, 43). The positions of wavelength
absorption bands in the spectra of synthesised dyes,
1a –1c, were determined in four organic solvents of
different polarities, namely DMF, DMSO, tetrahydroforan
(THF) and dioxane. The solvent effect on the spectral
position bands of 1a– 1c is summarised in Table 2. We
found that the absorption band at 360– 375 nm generally
shows red shift (positive solvatochromism) as the polarity
of solvent was increased. The influence of solvents for the
prepared dyes increases in the order DMSO . DMF . -
dioxane . THF. This observed behaviour is accounted as
that the prepared azo dyes in the ground state and in the
excitation state indicate different polarities. The other
band at 427 – 469 nm shows blue shift (negative solvato-
chromism) upon increasing solvent polarity, indicating a
 Supramolecular Chemistry 5

Table 2. Absorption spectral data of 1a – 1d in various organic solvents; lmax/nm (1/dm mol – 1 cm – 1).

Compounds DMSO DMF Dioxane THF

1a 375(29,933) 335(23,533) 246(12,566) 251(17,233)
464(5466) 466(7366) 350(31,366) 353(45,000)
1b 276(24,800) 275(23,266) 243(50,800) 274(42,600)
360(51,666) 356(48,366) 275(38,933) 278(18,600)
469(7433) 445(10,833) 355(48,566) 357(69,466)
434(8933) 450(7803)
1c 260(25,866) 270(27,533) 250(22,100) 243(36,466)
366(46,100) 362(49,133) 359(47,166) 296(22,266)
427(16,923) 433(15,066) 360(45,700)
1d 362(53,000) 361(52,700) 240(49,133) 244(41,633)
454(10,403) 463(13,366) 271(37,266) 304(37,000)
356(46,700) 356(68,666)
449(6200) 451(5600)
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reduction in the dipole moment upon electronic excitation.
The absorption spectra of 1b in various solvents are shown
in Figure 2.
3.5 UV –vis titration
The sensing behaviour of the receptors 1a – 1d towards
anions (F2, Cl2, Br2 and NO2 3 ) was also investigated by
the UV – vis titration (44 – 46). UV – vis titrations were
carried out by successive incremental addition of
tetrabutylammonium salts to 1a – 1d and the spectra are
shown in Figure 3. When increasing the concentration of
F2, in all these receptors 1a – 1d, a new red-shifted
absorption band at 390, 430, 470 and 445 nm were
gradually enhanced, while the intensity of absorption at
348, 351, 354 and 361 nm were decreased correspond-
ingly. The clear isosbestic points were observed at 375,
382, 390 and 387 nm for 1a – 1d, respectively. The
appearance of a single isosbestic point indicates the
presence of only two species, neutral host and its anion in
the solution. The negative charge brought about by the
anion-induced deprotonation increases the dipole
moment and stabilises the excited state causing a red
shift of 1a – 1d hosts. These results demonstrate that a
complex formation of 1a – 1d with F2 anion is taking
place via electrostatic interactions of hydrogen bonding
(Table 3). However, no change was observed with ions
Cl2, Br2 and NO2 3 in CH3CN/DMSO (Figure 3e).
Judging from the titrations, the strong binding of fluoride
allowed the Job’s plot method to be used in the
determination of the binding stoichiometry, which was
found to be a 1:1 host-to-anion complexation (Figure 3f).
3.6 Calculation of binding constant
The binding constants of receptors 1a– 1d were calculated
from the fluoride-induced absorption changes using
Equation (1) (47):
b 1 1 1
¼ £ þ ; ð1Þ
DA St K a D1 ½L
St D1

where DA is the change in absorbance, b is the path

Figure 2. Electronic spectra of 1b in various solvents with
different polarities.
length, St is the total concentration of substrate, Ka is the
association constant, D1 is the change in molar absorp-
tion coefficient. Plot can be made with 1/DA as a function
of 1/[L ]. The binding constant can be obtained by the
ratio of intercept and slope (see Supplementary
Information, Figure S1, available online). The binding
constant of the receptors with the corresponding anions is
summarised in Table 3. The detection limitation of
sensors towards F2 was obtained according to UV – vis
titration. The result can also be calculated from the
fluoride quantities added which made the initial changes
of absorbance of sensors 1a – 1d during the process of
UV – vis titration. The fluorimetric limit of detection of
1a – 1d were found to be 1.05 £ 1026, 1.01 £ 1026, 1.03
£ 1026 and 1.00 £ 1026 mol l21, respectively.
 6 R. Arabahmadi and S. Amani
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Figure 3. (a– d) A family of UV – vis spectra of hosts 1a – 1d were taken in the course of the titration of CH3CN/DMSO solution of
1a – 1d (4 £ 1025 M) with a standard solution of TBAF (c < 1.5 £ 1023 M) at 258C. (e) UV – vis absorbance increases of host 1b, in
CH3CN/DMSO, in relation to the free host, after addition of 2 equiv. Anions (lmax ¼ 351 nm). (f) Job’s plot of host 1b (2 £ 1025 M) with
fluoride, respectively.

Table 3. Data obtained from the UV – vis spectra upon titration of 1a – 1d with n-Bu4NþF2 in CH3CN/DMSO.

Receptor Receptor, lmax (nm) Complex, lmax (nm) Bathochromic shift, Dlmax (nm) Isosbestic point (nm) Ka (M – 1)
1a 348 390 42 375 5.725 £ 103
1b 351 430 79 382 6.200 £ 103
1c 354 470 116 390 8.200 £ 103
1d 361 445 84 387 5.890 £ 103

3.7 Sensor performance avoid the competing salvation effect of water (48–50), we
Generally, receptors for anions based solely on hydrogen prepared test strips of 1c for inspecting F2 in aqueous
bonding interactions cannot serve as efficient sensors in environments by putting a filter paper into the CH3CN/
aqueous media, due to the strong solvent competition. To DMSO solution of 1c (2.0 £ 1023 M) and then drying in
 Supramolecular Chemistry
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Figure 4. (Colour online) Photographs of the test kits with 1c
for detecting fluoride ion in neutral aqueous solution with
different F – concentrations. Left to right: (a) none (only 1c), (b)
10 mg/l, (c) 0.1 g/l and (d) 10 g/l.
vacuum (oven temperature 100–1108C, 60 mmHg). The test
strips containing 1c were utilised to sense different anions.
For detecting the fluoride anion in water, a test strip was
immersed in the test aqueous fluoride containing solution
(2 mM of 1c) for several seconds and then exposed to air or
in vacuum to remove water. An immediate obvious colour
change was observed only with different fluoride
concentrations. Other anions such as Cl2, Br2 and NO2 3
did not cause any detectable changes. In fact, sensing F – in
natural aqueous environments without any spectroscopic
instrumentation has been very useful in preventing fluorosis
caused by the fluoride toxicity in undeveloped regions.
However, since many other anions such as chloride were
present in most water at much higher concentrations than
fluoride, it was important to know that chloride did not
cause colour changes at concentrations normally found in
water. Consequently, the easy-to-prepare test kit can be
utilised to roughly and quantitatively detect and estimate the
concentration of fluoride ions. Figure 4 shows the colour
changes of the test paper with different fluoride
concentrations.
4. Conclusion
Compounds 1a – 1d proved to be a colorimetric fluoride
sensor that shows a selective colouration for fluoride
anion in CH3CN/DMSO. The colorimetric sensors
showed a colour change upon addition of fluoride ion
with a substantial red shift. No significant colour change
was observed upon addition of other anions, such as Cl2,
Br2 and NO2 3 in CH3CN/DMSO. The binding constants
of receptors 1a – 1d with fluoride ion show that the
electrostatic interaction between phenolic – OH of
receptors and fluoride anion is occurred. The easy-to-
prepare test kit based on the receptor system provides a
7
convenient and reliable detection of fluoride ions in
everyday applications.
Acknowledgements
The authors would like to thank the Research Council of Arak
University for the financial support of this research.
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 Supramolecular Chemistry 9

Raziyeh Arabahmadi and

Four new colorimetric chemosen-
Saeid Amani
sors, receptors 1a–1d containing
electron-donating moieties appended
A new fluoride ion colori-
to the azophenol moiety were syn-
metric sensor based on
thesized. The dyes were character- azo – azomethine receptors
ized by elemental analysis, IR, UV-
vis and NMR spectroscopy. Spectral
1 –9
characteristics of the dyes were
investigated in four organic solvents
of differing polarity and their chro-
mogenic behaviours toward various
anions.
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