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Journal of Materials Chemistry C
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Acknowledgements
acetate (1.5 g, 20.0 mmol), and acetic acid (15 mL) was refluxed
under nitrogen in oil bath. After 2 h, the mixture was cooled and
filtered. The solid product was washed with an acetic acid/water
mixture (1:1, 50 mL). And then, it was separated by chromatography
(petroleum ether/dichloromethane = 1:1 v/v) to afford a white solid.
DOI: 10.1039/C9TC02990G
We appreciate the National Key R&D Program of China (Grant
No. 2016YFB0401001), National Natural Science Foundation of
China (91833304, 21774047) and the Jilin Provincial Science
and Technology Department (20180201084GX).
1
(1.86 g, yield: 81%). H NMR (500 MHz, CDCl3) δ:9.14 (d, J = 6.9 Hz,
1H), 8.23 (d, J = 6.9 Hz, 1H), 8.20-8.12 (m, 2H), 8.08 (dd, J = 12.3, 8.2
Hz, 2H), 7.84-7.76 (m, 2H), 7.73 (t, J = 7.8 Hz, 1H), 7.65 (dd, J = 7.4,
2.1 Hz, 2H), 7.53-7.44 (m, 3H), 7.42-7.35 (m, 3H). MALDI-TOF (m/z):
[M+] Calcd for C29H17BrN2: 473.37; Found: 471.8.
9,10-(4-(9-phenyl-9H-pyreno[4,5-d]imidazole)-10-phenyl)
anthracene (C-BPyIA)
Notes and references
1
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2
In a 100 mL round flask, a mixture of C-PyIBr (2.13 g, 4.5 mmol), BAnB
(0.79 g, 1.8 mmol), K2CO3 (4.43 g, 32 mmol), distilled water (16 mL),
toluene (24 mL), and [Pd(PPh3)4] (0.62 g, 0.54 mmol) was added and
refluxed at 90 °C under N2 atmosphere for 48 h. The reaction was
then quenched by water and the mixture was extracted with
dichloromethane for three times. The organic phase was collected
and dried with anhydrous Na2SO4 for 30 min. After evaporation of
the solvent, the residue was purified via column chromatography
using THF as eluent to afford light yellow solid. (0.88 g, yield: 51%).
1H NMR (500 MHz, CD2Cl2) δ:8.33 (s, 2H), 8.29 – 8.10 (m, 9H), 8.09 –
7.91 (m, 8H), 7.90 – 7.69 (m, 13H), 7.68 – 7.46 (m, 8H), 7.43 (m, 2H).
13C NMR (126 MHz, CDCl3) δ:133.66, 132.94, 132.58, 131.94, 130.65,
130.02, 129.33, 128.72, 128.33, 127.64, 127.01, 126.29, 125.81,
124.25, 123.60, 122.64, 121.58. FTIR (KBr, ν, cm-1): 3040, 1921, 1791,
1597, 1496, 1452, 1387, 1297, 1221, 1185, 1149, 1102, 1070, 1019,
976, 944, 893, 828, 766, 720, 698, 665, 615, 550, 485, 420. MALDI-
TOF (m/z): [M+] Calcd for C72H42N4: 963.16; Found: 965.4. Anal. Calcd
for C72H42N4: C 89.79, H 4.40, N 5.82; Found: C 89.86, H 4.45, N 5.79.
9,10-(4-(10-phenyl-9H-pyreno[4,5-d]imidazole)-9-phenyl)
anthracene (N-BPyIA)
In a 100 mL round flask, a mixture of N-PyIBr (2.13 g, 4.5 mmol), BAnB
(0.79 g, 1.8 mmol), K2CO3 (4.43 g, 32 mmol), distilled water (16 mL),
toluene (24 mL), and [Pd(PPh3)4] (0.62 g, 0.54 mmol) was added and
refluxed at 90 °C under N2 atmosphere for 48 hours. The reaction was
then quenched by water and the mixture was extracted with
dichloromethane for three times. The organic phase was collected
and dried with anhydrous Na2SO4 for half an hour. After evaporation
of the solvent, the residue was purified via column chromatography
using THF as eluent to afford light yellow solid. (0.97 g, yield: 56%).
1H NMR (500 MHz, CD2Cl2) δ:8.33 (s, 2H), 8.27 – 8.23 (m, 4H), 8.22 –
8.10 (m, 5H), 8.07 – 7.91 (m, 9H), 7.90 – 7.68 (m, 12H), 7.68 – 7.45
(m, 9H), 7.45 – 7.38 (m, 1H). 13C NMR (126 MHz, CDCl3) δ:133.66,
132.67, 132.05, 130.93, 130.31, 129.90, 128.80, 128.36, 127.73,
127.24, 126.33, 125.63, 124.97, 124.16, 123.23, 122.74, 122.08,
121.03, 120.06, 118.38. FTIR (KBr, ν, cm-1): 3040, 1921, 1798, 1596,
1513, 1485, 1459, 1441, 1394, 1304, 1275, 1185, 1145, 1102, 1070,
1022, 976, 939, 896, 828, 770, 744, 715, 694, 669, 607, 557, 485, 416.
MALDI-TOF (m/z): [M+] Calcd for C72H42N4: 963.16; Found: 965.2.
Anal. Calcd for C72H42N4: C 89.79, H 4.40, N 5.82; Found: C 89.88, H
4.43, N 5.78.
3
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Conflicts of interest
There are no conflicts to declare.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 7
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