NJC
Paper
1H NMR (600 MHz, DMSO-d6) d (TMS, ppm): 8.95 (d, J = 6.9 Hz, (0.6 mmol, 198 g molÀ1, 0.119 g), cuprous iodide (0.3 mmol,
6H), 8.45 (d, J = 7.0 Hz, 6H), 8.12 (d, J = 8.8 Hz, 6H), 7.34 191 g molÀ1, 0.057 g), potassium hydroxide (6 mmol, 56 g molÀ1
(d, J = 8.8 Hz, 6H), 4.29 (s, 9H). 0.336 g), and toluene (20 mL) was added. Then, the mixture was
,
refluxed at 125 1C for 4 h. The reaction mixture was concentrated
by rotary evaporation. 4-Bromo-N-(4-bromophenyl)-N-phenyl-
À
4.10 Synthesis of TPA-Py-BF4À, TPA-diPy-BF4À, and TPA-triPy-BF4
Into a 100 mL round-bottom flask, TPA-Py-IÀ (0.7 mmol, aniline was purified by column chromatography on silica gel
464.3 g molÀ1, 0.325 g) and dichloroethane (30 mL) was added. (200–300 mesh) with a mixture of petroleum ether and ethyl
Further, AgBF4 (1.4 mmol, 194.7 g molÀ1, 0.273 g) was taken in acetate as the eluent (50 : 1 by volume); the solid was dried under
a vial and dichloroethane (2 mL) was added. Then, the AgBF4 vacuum at 30 1C overnight, obtaining a white solid (0.9 g, 75%
solution was added dropwise to the round-bottom flask using a yield). 1H NMR (600 MHz, DMSO-d6) d (TMS, ppm): 7.47–7.44 (m,
syringe. The reaction was stirred at room temperature for 4H), 7.36–7.32 (m, 2H), 7.11 (t, J = 7.4 Hz, 1H), 7.06–7.03 (m, 2H),
48 hours. Then, the mixture was extracted by adding water. 6.95–6.92 (m, 4H).
The organic phase was separated and concentrated by rotary
evaporation. The solid was dried under vacuum at 30 1C over-
Conflicts of interest
À
night. TPA-Py-BF4 was a yellow solid (0.232 g, 78% yield).
1H NMR (600 MHz, CDCl3) d (TMS, ppm): 8.57 (d, J = 6.9 Hz,
There are no conflicts to declare.
2H), 7.99 (d, J = 7.0 Hz, 2H), 7.63 (d, J = 9.0 Hz, 2H), 7.37–7.33
(m, 4H), 7.23–7.15 (m, 6H), 7.07 (d, J = 8.9ÀHz, 2H), 4.36 (s, 3H).
Acknowledgements
À
The synthetic process of TPA-diPy-BF4 and TPA-triPy-BF4À
This work is supported by the National Natural Science Foun-
dation of China (no. 21764012). We thank the Key Laboratory of
EcoEnvironment-Related Polymer Materials (Northwest Normal
University) and the Ministry of Education Scholars Innovation
Team (IRT 1177) for financial support. We also thank Prof.
Anjun, Qin, Dr Rong, Hu from SCUT (South China University of
Technology) and Prof. Dongfeng Dang, Dr Dehuai Li from Xi’an
Jiaotong University for their help and comments.
is the same as the above mentioned method. TPA-diPy-BF4
was a brown solid (0.23 g, 76% yield). 1H NMR (600 MHz, D2O)
d (TMS, ppm): 8.67 (d, J = 6.9 Hz, 4H), 8.24 (d, J = 7.0 Hz, 4H),
7.94 (d, J = 8.9 Hz, 4H), 7.52À–7.48 (m, 2H), 7.41–7.28 (m, 7H),
4.33 (s, 6H). TPA-triPy-BF4 was a brown solid (0.37 g,
1
75% yield). H NMR (600 MHz, DMSO-d6) d (TMS, ppm): 8.94
(d, J = 6.8 Hz, 6H), 8.44 (d, J = 6.8 Hz, 6H), 8.12 (d, J = 8.7 Hz,
6H), 7.34 (d, J = 8.7 Hz, 6H), 4.29 (s, 9H).
À
4.11 Synthesis of TPA-Py-PF6À, TPA-diPy-PF6À, and TPA-triPy-PF6
Notes and references
Into a 100 mL round-bottom flask, TPA-Py-IÀ (0.7 mmol,
464.3 g molÀ1, 0.325 g) and acetonitrile (30 mL) was added.
Further, NH4PF6À (1.75 mmol, 163 g molÀ1, 0.285 g) was taken in
a vial and deionized water (10 mL) was added. Then, the NH4PF6
solution was added dropwise to the round-bottom flask using
a syringe. The reaction was stirred at room temperature for
48 hours. After the reaction, the mixture was extracted by adding
water. The organic phase was separated and concentrated by
rotary evaporation. The solid was dried under vacuum at 30 1C
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an orange solid (0.27 g, 75% yield). H NMR (600 MHz, D2O) d
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(TMS, ppm): 8.67 (d, J = 7.0 Hz, 4H), 8.24 (d, J = 7.1 Hz, 4H), 7.94
(d, J = 8.8 Hz, 4H), 7.52–7.49 (m, 2H), 7.40–7.32 (m, 7H), 4.33
À
(s, 6H). TPA-triPy-PF6 was an orange solid (0.43 g, 72% yield).
1H NMR (600 MHz, DMSO-d6) d (TMS, ppm): 8.94 (d, J = 6.8 Hz,
6H), 8.44 (d, J = 7.0 Hz, 6H), 8.12 (d, J = 8.8 Hz, 6H), 7.34
(d, J = 8.8 Hz, 6H), 4.29 (s, 9H).
4.12 Synthesis of 4-bromo-N-(4-bromophenyl)-N-phenylaniline44
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g
,
This journal is ©The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019 New J. Chem., 2019, 43, 18251--18258 | 18257