High-yield synthesis of a novel water-soluble macrocycle for selective recognition of naphthalene
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* Corresponding author.
E-mail address: zengfei@iccas.ac.cn (F. Zeng).
Citation: Man-Hua Ding, Juan Liao, Lin-Li Tang, Guang-Chuan Ou, Fei Zeng. High-yield synthesis of a novel water-soluble macrocycle for selective recognition of naphthalene[J]. Chinese Chemical Letters, ;2021, 32(5): 1665-1668. doi: 10.1016/j.cclet.2020.11.019
K. Gloe, Macrocyclic Chemistry: Current Trends and Future Perspectives, Springer, Dordrecht, 2005.
F. Davis, S. Higson, Macrocycles: Construction, Chemistry and Nanotechnology Applications, Wiley, Chichester, 2011.
J.W. Steed, J.L. Atwood, Supramolecular Chemistry, 2nd ed., Wiley, Chichester, 2009.
C.F. Chen, Chem. Commun. 47(2011) 1674-1688.
doi: 10.1039/c0cc04852f
T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem. Rev. 116(2016) 7937-8002.
doi: 10.1021/acs.chemrev.5b00765
Y. Han, Z. Meng, Y.X. Ma, C.F. Chen, Acc. Chem. Res. 47(2014) 2026-2040.
doi: 10.1021/ar5000677
G. Yu, K. Jie, F. Huang, Chem. Rev. 115(2015) 7240-7303.
doi: 10.1021/cr5005315
M.X. Wang, Acc. Chem. Res. 45(2012) 182-195.
doi: 10.1021/ar200108c
E.X. Zhang, D.X. Wang, Q.Y. Zheng, M.X. Wang, Org. Lett. 10(2008) 2565-2568.
doi: 10.1021/ol800840m
R.B. Xu, Q.Q. Wang, Y.F. Ao, et al., Org. Lett. 19(2017) 738-741.
doi: 10.1021/acs.orglett.7b00070
T. Ogoshi, S. Kanai, S. Fujinami, T.A. Yamagishi, J. Am. Chem. Soc. 130(2008) 5022-5023.
doi: 10.1021/ja711260m
M. Xue, Y. Yang, X.D. Chi, Z.B. Zhang, F. Huang, Acc. Chem. Res. 45(2012) 1294-1308.
doi: 10.1021/ar2003418
N.L. Strutt, H. Zhang, S.T. Schneebeli, J.F. Stoddart, Acc. Chem. Res. 47(2014) 2631-2642.
doi: 10.1021/ar500177d
H. Chen, J. Fan, X. Hu, et al., Chem. Sci. 6(2015) 197-202.
doi: 10.1039/C4SC02422B
J. Ma, H. Deng, S. Ma, et al., Chem. Commun. 51(2015) 6621-6624.
doi: 10.1039/C5CC01470K
J. Ye, R. Zhang, W. Yang, et al., Chin. Chem. Lett. 31(2020) 1550-1553.
doi: 10.1016/j.cclet.2019.11.041
G.W. Zhang, P.F. Li, Z. Meng, et al., Angew. Chem. Int. Ed. 55(2016) 5304-5308.
doi: 10.1002/anie.201600911
Q. Shi, C.F. Chen, Org. Lett. 19(2017) 3175-3178.
doi: 10.1021/acs.orglett.7b01296
G.W. Zhang, Y. Han, Y. Wang, C.F. Chen, Chem. Commun. 53(2017) 10433-10436.
doi: 10.1039/C7CC05489K
G.B. Huang, S.H. Wang, H. Ke, et al., J. Am. Chem. Soc. 138(2016) 14550-14553.
doi: 10.1021/jacs.6b09472
L.L. Wang, Z. Chen, W.E. Liu, et al., J. Am. Chem. Soc. 139(2017) 8436-8439.
doi: 10.1021/jacs.7b05021
Y.L. Ma, H. Ke, A. Valkonen, K. Rissanen, W. Jiang, Angew. Chem. Int. Ed. 57(2018) 709-713.
doi: 10.1002/anie.201711077
Z. He, G. Ye, W. Jiang, Chem. Eur. J. 21(2015) 3005-3012.
doi: 10.1002/chem.201405912
J.S. Cui, Q.K. Ba, H. Ke, et al., Angew. Chem. Int. Ed. 57(2018) 7809-7814.
doi: 10.1002/anie.201803349
Z. Liu, S.K.M. Nalluri, J.F. Stoddart, Chem. Soc. Rev. 46(2017) 2459-2478.
doi: 10.1039/C7CS00185A
J.C. Barnes, M. Juríček, N.L. Strutt, et al., J. Am. Chem. Soc. 135(2013) 183-192.
doi: 10.1021/ja307360n
S.T.J. Ryan, J.D. Barrio, I. Ghosh, et al., J. Am. Chem. Soc. 136(2014) 9053-9060.
doi: 10.1021/ja5032437
I. Roy, S. Bobbala, R.M. Young, et al., J. Am. Chem. Soc. 141(2019) 12296-12304.
doi: 10.1021/jacs.9b03990
J. Zhou, Y. Wu, I. Roy, et al., Chem. Sci. 10(2019) 4282-4292.
doi: 10.1039/C8SC05514A
M. Juríček, J.C. Barnes, N.L. Strutt, et al., Chem. Sci. 5(2014) 2724-2731.
doi: 10.1039/c4sc00488d
M. Juríček, J.C. Barnes, E.J. Dale, et al., J. Am. Chem. Soc. 135(2013) 12736-12746.
doi: 10.1021/ja4052763
E.J. Dale, N.A. Vermeulen, A.A. Thomas, et al., J. Am. Chem. Soc. 136(2014) 10669-10682.
doi: 10.1021/ja5041557
Y. Chen, C. Qian, Q. Zhao, et al., Chem. Commun. 55(2019) 8072-8075.
doi: 10.1039/C9CC03577J
M. Cheng, J. Zhang, X. Ren, et al., Chem. Commun. 53(2017) 11838-11841.
doi: 10.1039/C7CC07469G
C. Zhang, Z. Wang, L. Tan, et al., Angew. Chem. Int. Ed. 54(2015) 9244-9248.
doi: 10.1002/anie.201502912
Z. Wang, Y. Luo, T.L. Zhai, et al., Org. Lett. 18(2016) 4574-4577.
doi: 10.1021/acs.orglett.6b02219
C. Zhang, Z. Wang, S. Song, et al., J. Org. Chem. 79(2014) 2729-2732.
doi: 10.1021/jo402884a
D.J. Hoffart, J. Tiburcio, A. de la Torre, L.K. Knight, S.J. Loeb, Angew. Chem. Int. Ed. 47(2008) 97-101.
doi: 10.1002/anie.200703019
L. Chen, Y.M. Zhang, Y. Liu, J. Phys. Chem. B 116(2012) 9500-9506.
doi: 10.1021/jp305503e
L. Chen, H.Y. Zhang, Y. Liu, J. Org. Chem. 77(2012) 9766-9773.
doi: 10.1021/jo301911w
X. Ji, M. Zhang, X. Yan, J. Li, Chem. Commun. 49(2013) 1178-1180.
doi: 10.1039/c2cc38472h
F. Zeng, C.F. Chen, Org. Boimol. Chem. 13(2015) 1988-1991.
doi: 10.1039/C4OB02533D
F. Zeng, L.L. Tang, X.M. Chen, et al., J. Org. Chem. 36(2016) 1937-1941.
Y. Ma, X. Ji, F. Xiang, et al., Chem. Commun. 47(2011) 12340-12342.
doi: 10.1039/c1cc15660h
B. Gómez, V. Francisco, F. Fernández-Nieto, et al., Chem. Eur. J. 20(2014) 12123-12132.
doi: 10.1002/chem.201403194
G. Wu, C.Y. Wang, T. Jiao, et al., J. Am. Chem. Soc. 140(2018) 5955-5961.
doi: 10.1021/jacs.8b01651
L. Shen, N. Cao, L. Tong, et al., Angew. Chem. Int. Ed. 57(2018) 16486-16490.
doi: 10.1002/anie.201811025
Y.K. Kryschenko, S.R. Seidel, D.C. Muddiman, et al., J. Am. Chem. Soc. 125(2003) 9647-9652.
doi: 10.1021/ja030209n
K.A. Connors, Binding Constants, J. Wiley and Sons, New York, 1987.
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