NMR (400 MHz, CDCl
s, 16H, ArH), 4.49 (d, J = 13.2 Hz, 4H, ArCH
m, 152H, CH O), 3.36, 3.31 (2 s, 36H, OCH ), 3.21 (d, J = 13.2
Hz, 4H, ArCH Ar), 1.96 (s, 8H, ArOCH CH CH ), 1.45–1.20 (m,
(CH CH ), 0.89 (t, J = 6.4 Hz, 12H, CH CH );
C NMR (100 MHz, CDCl ) d 165.1, 153.5, 152.4, 141.7, 135.2,
3
) d 8.26 (s, 4H, CONH), 7.20–7.0 (br
the Fundamental Research Funds for the Central Universities
(HUST: No. 2010ZD007) and the Analytical and Testing Centre
at Huazhong University of Science and Technology.
2
Ar), 4.20–3.40
(
2
3
2
2
2
2
5
6H, OCH
2
CH
2
2
)
7
3
2
3
1
3
References
3
1
7
3
1
32.4, 129.8, 121.3, 107.6, 75.5, 72.4, 72.0, 71.9, 70.68, 70.66,
0.60, 70.56, 70.5, 70.4, 69.8, 69.2, 59.0, 58.9, 32.0, 31.4, 30.3,
0.0, 29.8, 29.5, 26.4, 22.7, 14.1); IR (KBr) n 3308, 2925, 1663,
1
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(
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H
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N O56)/2 1704.0140 [M+2H ] /2, found [M+2H ] /2
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H NMR and C NMR spectra were measured on a 400 MHz
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spectrometer at 298 K in CDCl
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a TOF-MS instrument. Absorption spectra were recorded on a
UV–vis spectrophotometer. Infrared spectra were recorded on an
EQUINAX55 spectrometer. Transmission electron micrographs
2
007, 63, 5539–5547; (e) M. Strobel, K. Kita-Tokarczyk, A. Taubert,
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(
TEM) were recorded on a G2 20 electron microscope at 200 kV.
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The micelle suspension was dropped onto a copper grid covered
with a thin carbon film on filter paper and air dried. Fluorescent
emission spectra were collected on a fluorophotometer at 298 K.
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particle size analyzer. Fluorescent emission spectra were collected
on a fluorophotometer at 298 K.
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1
26, 7752–7753; (b) G. M. L. Consoli, G. Granata, E. Galante, I. Di
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2
007, 36, 254–266.
For the cryo-TEM experiment, the specimen were prepared in
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◦
a controlled environment vitrification system (CEVS) at 22
C
and 100% relative humidity to avoid loss of volatiles. A 3.5 mL
drop of solution was placed on a GiG 300 mesh holey carbon film
and blotted with filter paper (4 s) to form a thin liquid film of
the sample. The thin film sample was plunged into liquid ethane
7
8
R. Lalor, H. Baillie-Johnson, C. Redshaw, S. E. Matthews and A.
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◦
at its freezing temperature (-183 C) to get vitrified and then
◦
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0 (a) M. Kellermann, W. Bauer, A. Hirsch, B. Schade, K. Ludwig and
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1
specimens were examined in an FEI Tecnai 20 TEM operating at
1
1
1
an accelerating voltage of 200 kV. A Gatan CT3500 cryoholder
◦
that maintained the specimens below -180 C during sample
1
5, 1637–1648.
transfer and observation was used. The specimens were observed
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-
-2
and imaged at low dose mode with a dose of 20e A .
Fluorescent titration was carried out by addition of a concen-
trated solution of 1 into a solution of naproxen in H O. To keep
2
a constant concentration of naproxen and account for dilution
effects during titration, the solution of 1 was prepared with the
solution of naproxen at its initial concentration as a solvent. The
quenching constant was calculated using the following Stern–
(
4
9
1
1
4 L. C. Garzon and F. Martinez, J. Solution Chem., 2004, 33, 1379–1395.
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16
Volmer equation :
F
0
/F = 1 + KSV [Q],
1
26, 10640–10644.
1
6 J. R. Lakowicz, Principles of Fluorescence Spectroscopy,
where F
fluorescence intensity of naproxen upon addition of 1; [Q] is the
0
is the fluorescence intensity of naproxen; F is the
Kluwer/Plenum Press, New York, 1999.
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-
1
molar concentration (mole L ) of 1; and KSV is the quenching
-
1
constant (L mole ).
1
5, 639–645; (c) T. Heinlein, J.-P. Knemeyer, O. Piestert and M. Sauer,
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Acknowledgements
1
97, 149–155.
This research work was supported by the National Natural
Science Foundation of China (No. 20872040 and 21072067),
1
8 (a) M. Labieniec and T. Gabryelak, J. Photochem. Photobiol., B, 2006,
82, 72–78; (b) Cardoso, D. R. K. Olsen, J. K. S. Moller and L. H.
7
34 | Org. Biomol. Chem., 2012, 10, 729–735
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