SUPRAMOLECULAR CHEMISTRY
619
3.43–3.38 (m, 2 H, N-CH2-), 2.86 (t, J = 8.0 Hz, 2 H,-CH2-
L.; Tan, H.; Li, X.; Jin, G.; Yang, H. Angew. Chem. Int. Ed. 2017,
56, 14438; (j) Song, N.; Kakuta, T.; Yamagishi, T.; Yang,
Y Ogoshi, T. Chem. 2018, 4, 2029. (k) Shen, L; Zhao, Y.; Dai,
D.; Yang, Y.; Wu, B.; Yang, X. Chem. Commun. 2020, 56, 1381;
(l) Li, E.; Jie, K.; Fang, Y.; Cai P.; Huang, F. J. Am. Chem. Soc.
2020, 142, 15560. (m) Zhu, W.; Li, E.; Zhou, J.; Zhou, Y.;
Sheng, X.; Huang, F. Mater. Chem. Front. 2020, 4, 2325. (n)
Wu, X.; Duan, Q.; Ni, M.; Hu, X.; Wang, L. Chin.J. Org. Chem.
2014, 34, 437; (o) Zhang, R., Wang, C., Sun, J., Yan, C.; Yao,
Y. Chin .J. Org. Chem. 2019, 39, 3483; (p) Cao, Y.; Chen, Y.;
Zhang, Z.; Wang, J.; Yuan, X.; Zhao, Q.; Ding, Y.; Yao, Y. Chin.
Chem. Lett. 2020, 10.1016/j.cclet.2020.03.058.
NH2). 13C NMR (101 MHz, CDCl3) δ 169.43, 168.67, 157.17,
129.80, 122.10, 114.65, 67.31, 41.56, 41.25. MS (m/z):
+
HRMS (ESI) Calcd. for C10H15N2O2 ([Mb
195.1134, found: 195.1055.
+
H]+):
AA4: white solid, yield: 83.4%; 1H NMR (400 MHz, CDCl3)
δ 7.32 (t, J = 8.0 Hz, 2 H, ArH), 7.02 (t, J = 6.0 Hz, 1H, ArH),
6.93 (t, J = 8.0 Hz, 2 H, ArH), 4.49 (s, 2 H, -CH2-), 3.38–3.34 (m,
2 H, N-CH2-), 2.76 (t, J = 8.0 Hz, 2 H,-CH2-NH2), 1.70–1.56 (m,
2 H, -CH2-), 1.50–1.43 (m, 2 H, -CH2-). 13C NMR (101 MHz,
CDCl3) δ 168.85, 157.25, 129.74, 121.97, 114.72, 67.19,
40.17, 38.52, 26.60, 26.58. MS (m/z): HRMS (ESI) Calcd. for
C12H19N2O2+ ([Mc + H]+): 223.1447, found: 223.1368.
AA6: white solid, yield: 64.3%, 1H NMR (400 MHz,
CDCl3) δ 7.32 (t, J = 8.0 Hz, 2H, ArH), 7.03 (t, J = 6.0 Hz,
1H, ArH), 6.92 (d, J = 8.0 Hz, 2H, ArH), 4.49 (s, 2H, -CH2-),
3.37–3.30 (m, 2H, N-CH2-), 2.67 (t, J = 8.0 Hz, 2H,-CH2-
NH2), 1.55–1.53 (m, 4 H, -CH2-), 1.43–1.41 (m, 2H, -CH2-),
1.34–1.31 (m, 4 H, -CH2-).13C NMR (101 MHz, CDCl3) δ
168.19, 168.17, 157.18, 129.79, 122.10, 114.64, 67.32,
67.31, 41.87, 38.93, 33.14, 29.49, 29.42, 26.61, 26.44,
[2] (a) Ogoshi T, Kanai S, Fujinami S, et al. J. Am. Chem. Soc.
2008, 130, 50223; (b) Xia, D.; Wang, P.; Ji, X.; Khashab, N.;
Sessler, J.; Huang, F. Chem. Rev. 2020, 120, 6070; (c) Feng,
W.; Jin, M.; Yang, K.; Pei, Y.; Pei, Z. Chem. Commun. 2018,
54, 13626; (d) Xiao, C.; Wu, W.; Liang, W.; Zhou, D.;
Kanagaraj, K.; Cheng, G.; Su, D.; Zhong, Z.; Chruma, J.;
Yang, C. Angew. Chem. Int. Ed. 2020, 59, 8094; (e) Shao, L.;
Pan, Y.; Hua, B.; Xu, S.; Yu, G.; Wang, M.; Liu, B.; Huang,
F. Angew. Chem. Int. Ed. 2020, 59, 11779; (f) Zeng, X.;
Deng, H.; Jia, X.; Cui, L.; Li, J.; Li, C.; Fang, J. Chem.
Commun. 2018, 54, 11634; (g) Zhang, D.; Cheng, J.; Wei,
L.; Song, W.; Wang, L.; Tang, H.; Cao, D. J. Phys. Chem. Lett.
2020, 11, 2021; (h) Sun, G.; Qian, W.; Jiao, J.; Han, T.; Shi,
Y.; Hu, X.; Wang, L. J. Mater. Chem. A. 2020, 8, 9590; (i)
Xiao, T.; Qi, L.; Zhong, W.; Lin, C.; Wang, R.; Wang,
L. Mater. Chem. Front. 2019, 3, 1973; (j) Zhu, Y.; Xu, L.;
Wang, L.; Tang, H.; Cao, D. Chem. Commun. 2019, 55,
5910; (k) Yang, K.; Yang, K.; Chao, S.; Wen, J.; Pei, Y.; Pei,
Z. Chem. Commun. 2018, 54, 9817; (l) Cai, Y.; Zhang, Z.;
Ding, Y.; Hu. L.; Wang, J.; Chen, T.; Yao, Y. Chin. Chem.
Lett., 2020, 10.1016/j.cclet.2020.10.036.
+
26.31. MS (m/z): HRMS (ESI) Calcd. for C14H23N2O2
([M + H]+): 251.1760, found: 251.1681.
Disclosure statement
No potential conflict of interest was reported by the authors.
[3] (a)Yang J, Dai D, Luo X, et al. Theranostics. 2020, 10, 615;
(b) Fan, J.; Chen, Y.; Cao, D.; Yang, Y.; Jia, X.; Li, C. RSC. Adv.
2014, 4, 4330; (c) Ma, Y.; Chi, X.; Yan, X.; Liu, J.; Yao, Y.;
Chen, W.; Huang, F.; Hou, J. Org. Lett. 2012, 14, 1532; (d) Li,
M.; Han, K.; Li, J.; Jia, X.; Li, C. Acta Polymerica Sinica, 2017,
1, 129; (e) Ogoshi, T.; Demachi, K.; Kitajima, K.; Yamagishi,
T. Chem.Commun. 2011, 47, 7164; (f) Park, J.; Choi, Y.; Lee,
S, S.; Jung, J, H.; Org. Lett. 2019, 21, 1232.
Funding
This work was funded by the National Natural Science
Foundation of China (No. 21801139, 21871227), Natural
Science Foundation of Jiangsu Province (No. BK20180942),
the Natural Science Foundation of Nantong University for
High-Level Talent (No. 03083046), and the Foundation for
Jiandsu Specially-Appointed Professor (No. 06190019);
[4] (a)Chen W, Zhang Y, Li J, et al. Chem Commun. 2013, 49,
7956; (b) Ma, Y.; Ji, X.; Xiang, F.; Chi, X.; Han, C.; He, J.; Abliz,
Z.; Chen, W.; Huang, F. Chem. Commun. 2011, 47, 12340.
National
Natural
Science
Foundation
of
China
[21801139,21871227]; Natural Science Foundation of Jiangsu
Province [BK20180942];
[5] (a)Chen J, Ni H, Meng Z, et al. Nature Commun. 2019, 10,
3546. (b) Yuan, M.; Chen, H.; Du, X.; Li, J.; Wang, J.; Jia, X.;
Li, C. Chem. Commun. 2015, 51, 16361; (c) Wang, Y.; Ping,
G.; Li, C. Chem. Commun. 2016, 52, 9858. (d) Shi, H.;
Cheng, X.; Lin, Q.; Yao, H.; Zhang, Y.; Wei, T. Chin. J. Org.
Chem. 2018, 38, 1718; (d) Shu, X.; Fan, J.; Li, J.; Wang, X.;
Chen, W.; Jia, X. and Li, C. Org. Biomol. Chem., 2012, 10,
3393-3397; (e) Xiong, S.; Zhang, X.; Meng, L.-B.; Jiang, J.;
Lin, C. and Wang, L. Chem. Commun. 2015, 51, 6504-
6507; (f) Du, X.-S.; Wang, C.-Y.; Jia, Q.; Deng, R.; Tian, H.-
S.; Zhang, H.-Y.; Meguellati, K. and Yang, Y.-W. Chem.
Commun. 2017, 53, 5326-5329.
References
[1] (a) Zhang M, Zhu P, Xin P, et al. Angew. Chem. Int. Ed. 2017,
56, 2999; (b) Kakuta, T.; Yamagishi, T.; Ogoshi, T. Acc. Chem.
Res. 2018, 51, 1656; (c) Chen, J.; Wang, Y.; Long, R.; Chen, T.;
Yao, Y. Chem. Commun. 2019, 55, 6817; (d) Guo, M.; Wang,
X.; Zhan, C.; Demay-Drouhard, P.; Li, W.; Du, K.; Olson, M. A.;
Zuilhof, H.; Sue, A. C.-H. J. Am. Chem. Soc. 2018, 140, 74; (e)
Sun, S.; Geng, M.; Huang, L.; Chen, Y.; Cen, M.; Lu, D.; Wang,
A.; Wang, Y.; Shi Y.; Yao, Y. Chem. Commun. 2018, 54, 13006;
(f) Song, N.; Lou, X.; Yu, H.; Weiss, P. S.; Tang, B.; Yang,
Y. Mater. Chem. Front. 2020, 4, 950. (g) Xu, L.; Wang, Z.;
Wang, R.; Wang, L.; He, X.; Jiang, H.; Tang, H.; Cao, D.;
Tang, B. Angew. Chem. Int. Ed. 2020, 59, 9908; (h) Zhou, Y.;
Jie, K.; Huang, F. Chem. Commun. 2018, 54, 12856. (i) Jiang,
B.; Wang, W.; Zhang, Y.; Liu, Y.; Zhang, C.; Yin, G.; Zhao, X.; Xu,
[6] Shu X, Chen S, Li J, et al. Chem. Commun. 2012, 48, 2967.
[7] Lou X, Chen H, Jia X, et al. Chin. J. Chem. 2015, 33, 335. 3
[8] Ashton P, Ballardini R, Balzani V, et al. J. Am. Chem. Soc.
[9] Su S, Zhou X, Liao G, et al. Molecules. 2017, 22, 64