a
Table 1 Comparative results of HOCl detection in tap water
solvent and concentration in vacuum gave the crude product.
Yellowish product 1 was purified by crystallization from CH
2
Cl
, 600 MHz): d 8.56 (d, J = 12.0 Hz,
H), 8.33 (d, J = 6.0 Hz, 1H), 8.21–8.16 (m, 4H), 8.08–8.00 (m,
3H), 6.23 (s, 1H), 3.32–3.27 (m, 2H), 3.07–3.03 (m, 2H), 2.33–2.28
2
b
c
Samples
Conc. (ppm)
Conc. (ppm)
Relative Error (%)
1
and CH
3
OH. H NMR (CDCl
3
1
Tap water 1
Tap water 2
Tap water 3
Average
0.18
0.19
0.18
0.183
0.179
0.182
0.175
0.179
0.48
4.18
2.68
2.45
13
(
1
m, 1H), 2.14–2.06 (m, 1H). C NMR (CDCl
31.4, 131.3, 130.7, 127.9, 127.9, 127.8, 127.3, 126.0, 125.9, 125.5,
125.3, 125.2, 124.9, 124.8, 122.7, 48.9, 32.9, 25.4. HRMS (DIP)
3
, 150 MHz): d 132.2,
a
-6
Measured at 457 nm. [1] = 5.0 ¥ 10 M in a mixture of CH
3
CN and acetate
b
buffer solution (pH = 5.0, 10 mM), (1 : 1, v/v). lex = 340 nm. Measured
+
m/z calcd for C20
H
16
S [M] 320.0693; found, 320.0693.
2
28 c
by DPD-method. Measured by 1.
Analysis of hypochlorite in bleach and tap water
Concentration of HOCl in commercial bleaches was determined
13
by iodometry. Stock solutions of each sample (1.0 mM) were
-
4
prepared in distilled water. Stock solution of 1 (5.0 ¥ 10 M)
in CH CN and acetate buffer solution (1.0 M) in distilled water
3
were also prepared. Test solutions were prepared by placing 30
mL of stock solution of 1, 30 mL of acetate buffer solution, and
various volume (0–30 mL) of each sample containing HOCl (1.0
mM) in a vial. The resulting solutions were diluted to 3.0 mL
with distilled water and CH
3
CN to make a final composition of
1
¥
: 1, v/v. The final concentration of 1 and acetate buffer was 5.0
10 M and 1.0 ¥ 10 M, respectively. Free chlorine in tap water
28
-
6
-2
was measured by published procedure using DPD-method. To
measure HOCl concentration in tap water with present method,
test solutions were prepared by placing 30 mL of stock solution
of 1, acetate buffer solution, and 1.47 mL of tap water in a vial.
The test solutions were diluted to a final volume of 3.0 mL with
Fig. 8 Concentration-dependent fluorescence signaling of HOCl and
-6
commercial bleaches by 1. Measured at 457 nm. [1] = 5.0 ¥ 10 M in
a mixture of CH CN and acetate buffer solution (pH = 5.0, 10 mM), (1 : 1,
v/v). lex = 340 nm.
3
CH CN. Concentration of HOCl in tap water was calculated by
3
using a linear calibration plot obatined by measuring fluorescence
intensities at 457 nm. Measurements of each solution were carried
out in triplicate.
2
+
common metal ions and anions. Interference from Hg ions could
be readily circumvented by using Chelex-100 resin. Furthermore,
selectivity over another important oxidant of hydrogen peroxide
was also observed.
Acknowledgements
Experimental section
This work was supported by a fund from Korea Research
Foundation of Korean Government (2011-0004870).
1
-Pyrenecarboxaldehyde 2, 1,3-propanedithiol, and iodine were
purchased from Aldrich Chemical Co. and used without further
purification. All solvents were purchased from Aldrich Chemical
Notes and references
1
Co. as ‘anhydrous’ or ‘spectroscopic grade’. H NMR (600 MHz)
1
3
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2
2
Cl (5 mL) was
6
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2
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dried over anhydrous MgSO and filtered. Evaporation of the
2
S
2
O
3
(0.1
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2
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014 | Org. Biomol. Chem., 2011, 9, 7011–7015
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