10.1002/ejic.201800280
European Journal of Inorganic Chemistry
FULL PAPER
obtained by the RF-5301PC fluorescence spectrometer (Shimadzu) at a
slit of 3.0 nm with a fast scanning speed. Dynamic light-scattering (DLS)
measurements were measured using a Malvern ZEN3600 Zetasizer (UK)
equipped with a 632.8 nm He-Ne laser and an avalanche photodiode
detector. The field emission scanning electron microscopy (FE-SEM)
images were performed on Zeiss Sigma FESEM (20 KV). Transmission
Preparation of the AIE-MSNs and CTAB-MSNs .
AIE-MSNs were prepared regularly by two steps with the mixture of
CTAB and C16-TPE-C16. Briefly, CTAB and C16-TPE-C16 with a total
amount of 0.137 mmol were dissolved in ultrapure water (25 mL) firstly.
The molar ratio of CTAB and C16-TPE-C16 was as followed CTAB : C16
-
TPE-C16 = n : 1 (n= 50, 40, 35, 30, 25, 20, 15, 10 and 5). Then, the
aqueous solution of NaOH (0.180 mL, 2.00 M) was introduced into the
solution. The temperature of the mixture was adjusted to 80 ºC and kept
for 30 min. TEOS (0.50 mL, 2.24 mmol) was added dropwise under
vigorous stirring. The mixture was allowed to react for 4 h to give a white
precipitate. The obtained product was collected by centrifugation and
extensively washed with water and ethanol to yield AIE-SNs. Finally, the
synthesized AIE-SNs (0.1 g) were refluxed for 24 h in a solution of
ethanol (10.0 mL) and HCl (0.6 mL, 37.4%) to remove the CTAB. The
product was collected by centrifugation, washed with water and ethanol
extensively and dried in vacuum at 35 ºC to yield AIE-MSNs. The
preparation of comparing CTAB-MSNs was performed with the same
amount of pure CTAB surfactant according to the literature.[12a]
electron microscopy (TEM) images were recorded on
a JEM-2100
microscope operated at 200 KV. The surface tension values were
measured on a QBZY-2 tensiometer (FANGRUI Corporation, Shanghai,
China) following the wilhelmy plate procedure at 25.0 ºC. The electrical
conductivity was performed on
a WTW conductivity meter (inoLab
Cond730, Germany) at 25.0 ºC. Nitrogen adsorption-desorption
isotherms were carried out at 77 K on a Micromeritics ASAP 2020
system (Norcross, USA). The Brunauer-Emmett-Teller (BET) method
was utilized to calculate the specific surface areas. The Barrett-Joyner-
Halenda (BJH) method was conducted to calculate the sample pore size
from the desorption branches of the isotherms.
Preparation of the C16-TPE-C16
.
The AIE gemini surfactant C16-TPE-C16 was synthesized according to the
procedures described in Scheme S1.
Acknowledgements
(i) The synthesis of TPE-2OH (compound 1) was performed by the
McMurry reaction as reported previously.[18, 23] Yield: 46 %. 1H NMR (400
MHz, CDCl3): δ 7.11-7.15 (m, 6 H), 7.01-7.10 (m, 4 H), 6.95-7.00 (m, 4
H), 6.54-6.59 (m, 4 H).
This work was supported by the Fundamental Research Funds
for the Chinese Central Universities. (2012203020211).
Keywords: aggregation-induced emission • gemini surfactant •
(ii) Synthesis of TPE-2Br (compound 2): TPE-2OH (0.24 g, 0.66 mmol)
and K2CO3 (0.27 g, 1.98 mmol) were mixed in acetone (30 mL). Then,
1,2-dibromoethane (0.372 g, 1.98 mmol) was added dropwise after
stirred for 30 min. The resulting mixture was refluxed for 24 h (monitored
by TLC) and cooled down to room temperature. After the filtration of
insoluble K2CO3, the crude product was obtained by evaporation of
shape-control
nanoparticles
•
fluorescent hollow mesoporous
•
silica
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a white powder after
purification by silica gel chromatography with eluents of petroleum
ether/ethyl acetate (8:1 (v/v)). Yield: 75 %. 1H NMR (400 MHz, DMSO-d6):
δ 7.07-7.17 (m, 6 H), 6.93-6.98 (m, 4 H), 6.83-6.89 (m, 4 H), 6.69-6.76
(m, 4 H), 4.21-4.26 (m, 4 H), 3.74-3.79 (m, 4 H). 13C NMR (400 MHz,
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acetate (20 mL). The resulting mixture was refluxed for 5 days. After the
reaction mixture cooled down to room temperature, the white precipitate
(crude product) was collected by filtration. The product was further
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Yield: 42 %. 1H NMR (400 MHz, CDCl3): δ 7.06-7.12 (m, 6 H), 6.96-6.99
(m, 4 H), 6.89-6.93 (m, 4 H), 6.58-6.67 (m, 4 H), 4.37-4.43 (m, 4 H), 4.12-
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143.47, 139.84, 137.73, 132.78, 131.27, 127.81, 126.59, 113.81, 66.31,
62.31, 52.09, 31.94, 29.72, 29.68, 29.64, 29.61, 29.53, 29.49, 29.47,
29.43, 29.39, 29.31, 29.28, 26.28, 22.99, 22.71, 14.18. IR (KBr, cm-1):
3019 (m), 2921 (vs), 2851 (vs), 1605 (s), 1509 (vs), 1467 (s), 1241 (vs),
1177 (s), 1057 (m), 725(m), 702 (s). UV-Vis: λmax=315 nm. MS-ESI
(CH3OH, m/z): [M-Br]+, calcd 1037.5, found 1037.4; [M-2Br]2+/2, calcd
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