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New Journal of Chemistry
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ARTICLE
C25H18BBrF2N2O: 490.1; found: 489.6 (Figure S19). IR (KBr, (Figure S30)
Journal Name
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cm-1): 669, 694, 1384, 1456, 1505, 1522, 1540, 1557, 1652, C29H28BF2N3O: 483.2; found: 484.6 [M + H] (Figure S31). IR
+
DOI: 10.1039/C9NJ02410G
1683, 2849, 2923, 3125.
4-(6,8-Di-tert-butyl-2,2-difluoro-2H-2λ4,3λ4-
(KBr, cm-1): 669, 695, 1038, 1382, 1457, 1506, 1521, 1558,
1653, 1682, 1701, 1734, 1773, 2848, 2923, 3126.
benzo[e][1,3,2]oxazaborinine-3yl)-N,N-diphenylaniline (TST
)
Following the synthetic procedure of TSH, TST was synthesized
Conflicts of interest
There are no conflicts of interest to declare.
from 4-aminotriphenylamine (0.70 g, 2.69 mmol) and 3,5-(di-
tertbutyl)salicylaldehyde (0.63 g, 2.69 mmol) and boron
trifluoride diethyl ether complex (0.50 mL, 3.96 mmol). The
crude product was purified by column chromatography (silica
gel, petroleum ether/CH2Cl2, v/v = 1/1) to afford TST (0.62 g,
81%) as a yellowish green solid. m.p. 213.0-214.0 C; 1H NMR
(400 MHz, DMSO-d6) δ 9.10 (s, 1 H), 7.66 (s, 2 H), 7.57 (d, J =
8.8, 2 H), 7.37 (t, J = 7.8, 4 H), 7.17 – 7.02 (m, 8 H), 1.42 (9 H,
s), 1.30 (9 H, s) (Figure S20). 13C NMR (100 MHz, DMSO-d6)
δ 164.95, 155.15, 147.82, 146.62, 141.72, 137.50, 135.78,
132.63, 129.76, 127.38, 124.67, 124.47, 123.92, 122.28, 116.14,
34.66, 34.03, 30.99, 29.08 (Figure S21). 11B NMR (128 MHz,
DMSO-d6) δ 0.76 (Figure S22). MALDI-TOF MS: m/z:
calculated for C33H35BF2N2O: 524.3; found: 524.3 (Figure S23).
IR (KBr, cm-1): 669, 695, 753, 1055, 1384, 1491, 1508, 1559,
1624, 1652, 1683, 1700, 2868, 2959, 3157.
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Acknowledgements
This work was financially supported by the National Natural
Science Foundation of China (21503090 and 51773076) and the
Open Project of State Key Laboratory of Supramolecular
Structure and Materials (SKLSSM2019019).
Notes and references
1
(a) Y. Jiang, D. Gindre, M. Allain, P. Liu, C. Cabanetos and J.
Roncali, Adv. Mater., 2015, 27, 4285-4289; (b) R. Pashazadeh,
P. Pander, A. Bucinskas, P. J. Skabara, F. B. Dias and J. V.
Grazulevicius, Chem. Commun., 2018, 54, 13857-13860; (c) S.
Yagai, T. Seki, H. Aonuma, K. Kawaguchi, T. Karatsu, T. Okura,
A. Sakon, H. Uekusa and H. Ito, Chem. Mater., 2016, 28, 234-
241; (d) B. Hupp, J. Nitsch,; T. Schmitt, R. Bertermann, K.
Edkins, F. Hirsch, I. Fischer, M. Auth, A. Sperlich and A. Steffen,
Angew. Chem. Int. Ed., 2018, 57, 13671-13675.
4-(4-Methoxy-2,2-difluoro-2H-2λ4,3λ4-
benzo[e][1,3,2]oxazaborinine-3yl)-N,N-diphenylaniline (TSO
)
Following the synthetic procedure of TSH TSO was
,
synthesized from 4-aminotriphenylamine (0.52 g, 2.00 mmol)
and 4-(methoxyl)salicylaldehyde (0.30 g, 1.97 mmol) and boron
trifluoride diethyl ether complex (0.50 mL, 3.97 mmol). The
crude product was purified by column chromatography (silica
gel, petroleum ether/ethyl acetate, v/v = 1/1) to afford TSO (0.40
2
(a) P. Galer, R. C. Korošec, M. Vidmar and B. Šket, J. Am. Chem.
Soc., 2014, 136, 7383–7394; (b) Z. Li, M. Li, G. Liu, Y. Wang, G.
Kang, C. Li and H. Guo, Dyes Pigment, 2019, 160, 597-603; (c)
S. Mula, N. Leclerc, P. Levꢀ que, P. Retailleau and G. Ulric, J.
Org. Chem., 2018, 83, 14406-14418; (d) Y. Kubota, K. Kasatani,
1
g , 46%) as a yellowish green solid. m.p. 239.0-240.0 C . H
H. akai, K. Funabiki and M. Matsui, Dalton Trans., 2015, 44
,
NMR (400 MHz, DMSO-d6) δ 8.98 (s, 1H), 7.69 (d, J = 8.7 Hz,
1H), 7.52 (d, J = 8.5 Hz, 2H), 7.35 (t, J = 7.4 Hz, 4H), 7.13 –
7.01 (m, 8H), 6.71 (d, J = 8.8 Hz, 1H), 6.63 (s, 1H), 3.89 (s, 3H)
(Figure S24). 13C NMR (100 MHz, DMSO-d6) δ 169.21, 163.57,
161.91, 148.38, 147.62, 137.07, 135.74, 130.66, 125.43, 125.30,
3326-3341; (e) H. Liu, H. Lu, J. P. Liu, Z. F. Li, J. Mack and Z.
Shen, Chem. Commun. 2014, 50, 1074-1076.
3
4
(a) K. Tanaka and Y. Chujo, NPG Asia Materials, 2015, 7, e233;
(b) T. M. Butler, C. Zhuang and C. L. Fraser, J. Phys. Chem. C,
2018, 122, 19090−19099; (c) W. Huang, X. Zhang, B. Chen, H.
Miao, C. O. Trindle, Y. Wang, Y. Luo and G. Zhang, Chem.
Commun., 2019, 55, 67-70; (d) E. V. Fedorenko, A. G.
124.71, 123.54, 111.15, 110.78, 102.12, 57.06 (Figure S25). 11
B
Mirochnik, V. G. Andrei and A. Yu, Dyes Pigment, 2018, 159
557–572.
,
NMR (128 MHz, DMSO-d6) δ 0.79 (Figure S26) MALDI-TOF
.
MS: m/z: calculated for C26H21BF2N2O2: 442.2; found: 443.5 [M
+ H]+ (Figure S27). IR (KBr, cm-1): 669, 695, 752, 1036, 1382,
1490, 1506, 1558, 1652, 1683, 1701, 2851, 2922, 3124.
4-(4-Diethylamino-2,2-difluoro-2H-2λ4,3λ4-
(a) G. Zhang, J. Lu, M. Sabat and C. L. Fraser, J. Am. Chem. Soc.,
2010, 132, 2160-2162; (b) N. D. Nguyen, G. Zhang, J. Lu, A. E.
Shermana and C. L. Fraser, J. Mater. Chem., 2011, 21, 8409-
8415; (c) T. Liu, A. D. Chien, J. Lu, G. Zhang and C. L. Fraser, J.
Mater. Chem., 2011, 21, 8401-8408; (d) W. A. Morris, T. Liu
benzo[e][1,3,2]oxazaborinine-3yl)-N,N-diphenylaniline (TSN
)
and C. L. Fraser, J. Mater. Chem. C, 2015, 3, 352-363; (e) T.
Following the synthetic procedure of TSH TSN was
,
Butler, W. A. Morris, J. Samonina-Kosicka and C. L. Fraser,
Chem. Commun., 2015, 51, 3359-3362; (f) T. Butler, W. A.
Morris, J. Samonina-Kosicka and C. L. Fraser, ACS Appl. Mater.
synthesized from 4-aminotriphenylamine (0.83 g, 3.19 mmol)
and 4-(diethylamino)salicylaldehyde (0.62 g, 3.19 mmol) and
boron trifluoride diethyl ether complex (0.88 mL, 10.49 mmol).
The crude product was purified by column chromatography
(silica gel, petroleum ether/ethyl acetate, v/v = 2/1) to afford
TSN (0.43 g, 51%) as a yellowish green solid. m.p. 91.0-92.0 C.
1H NMR (400 MHz, DMSO-d6) δ 8.64 (s1, H), 7.46 (t, J= 8.4
Hz, 3 H), 7.33 (t, J = 7.3 Hz, 4H), 7.07 (dd, J = 18.2, 7.8 Hz, 8H),
6.53 ( d, J= 9.1Hz, 1 H), 6.15 (s, 1 H), 3.48 (q , J = 6.8 Hz, 4 H),
1.15 (t, J = 6.8 Hz, 6 H) (Figure S28). 13C NMR (100 MHz,
DMSO-d6) δ 160.69, 158.97, 155.70, 146.92, 146.38, 137.23,
134.69, 129.67, 124.12, 123.90, 123.43, 106.60, 96.72, 26.35,
12.52 (Figure S29). 11B NMR (128 MHz, DMSO-d6) δ 0.74
Interfaces, 2016, 8, 1242-1251.
5
6
(a) R. Yosii, K. Suenaga, K. Tanaka, Y. Chujo, Chem. Eur. J., 2015,
21, 7231-7237; (b) M. Yamaguchi, S. Ito, A. Hirose, K. Tanaka,
Y. Chujo, J. Mater. Chem. C, 2016, 4, 5314-5319; (c) K. Suenaga,
K. Tanaka, Y. Chujo, Eur. J. Org. Chem. 2017, 5191-5196; (d) K.
Suenaga, K. Tanaka, Y. Chujo, Chem. Eur. J., 2017, 23, 1409-
1414.
(a) J. Y. Zhao, J. Peng, P. Chen, H. R. Wang, P. C. Xue and R. Lu,
Dyes Pigment, 2018, 149, 276-283; (b) J. B. Sun, J. B. Sun, W.
H. Mi, P. C. Xue, J. Y. Zhao, L. Zhai and R. Lu, Dyes Pigment,
2017, 136, 633-640; (c) H. Yang, K. Q. Ye, J. B. Sun, P. Gong and
R. Lu, Asian J. Org. Chem., 2017, 6, 199-206; (d) Z. Wu, J. B.
Sun, Z. Q. Zhang, H. Yang, P. C. Xue and R. Lu, Chem. Eur. J.,
6 | J. Name., 2012, 00, 1-3
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