Recent advances in click-derived macrocycles for ions recognition
- Corresponding author: Cao Qianyong, cqyong@ncu.edu.cn 1 These authors contributed equally to this work
Citation:
Peng Rongpeng, Xu Youliang, Cao Qianyong. Recent advances in click-derived macrocycles for ions recognition[J]. Chinese Chemical Letters,
;2018, 29(10): 1465-1474.
doi:
10.1016/j.cclet.2018.09.001
J.M. Lehn, Science 260(1993) 1762-173.
J.W. Lee, S. Samal, N. Selvapalam, H.J. Kim, K. Kim, Acc. Chem. Res. 36(2003) 621-630.
doi: 10.1021/ar020254k
G.W. Gokel, W.M. Leevy, M.E. Weber, Chem. Rev. 104(2004) 2723-2750.
doi: 10.1021/cr020080k
A.E. Hargrove, S. Nieto, T. Zhang, J.L. Sessler, E.V. Anslyn, Chem. Rev. 111(2011) 6603-6782.
doi: 10.1021/cr100242s
H. Li, Y.W. Yang, Chin. Chem. Lett. 24(2013) 545-552.
doi: 10.1016/j.cclet.2013.04.014
C.W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 67(2002) 3057-3064.
doi: 10.1021/jo011148j
V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41(2002) 2596-2599.
M. Meldal, C.W. Tornøe, Chem. Rev. 108(2008) 2952-3015.
doi: 10.1021/cr0783479
V.K. Tiwari, B.B. Mishra, K.B. Mishra, et al., Chem. Rev. 116(2016) 3086-3240.
doi: 10.1021/acs.chemrev.5b00408
Y.H. Lau, P.J. Rutledge, M. Watkinson, M.H. Todd, Chem. Soc. Rev. 40(2011) 2848-2866.
doi: 10.1039/c0cs00143k
J.J. Cai, J.L. Sessler, Chem. Soc. Rev. 43(2014) 6198-6213.
doi: 10.1039/C4CS00115J
J.C. Jewett, C.R. Bertozzi, Chem. Soc. Rev. 39(2010) 1272-1279.
doi: 10.1039/b901970g
Y.Y. Zhu, G.T. Wang, Z.T. Li, Org. Biomol. Chem. 7(2009) 3243-3250.
doi: 10.1039/b907457k
K.D. Bodine, D.Y. Gin, M.S. Gin, J. Am. Chem. Soc. 126(2004) 1638-1639.
doi: 10.1021/ja039374t
K.D. Bodine, D.Y. Gin, M.S. Gin, Org. Lett. 7(2005) 4479-4482.
doi: 10.1021/ol051818y
R. Leyden, P.V. Murphy, Synlett 12(2009) 1949-1950.
N.H. Evans, P.D. Beer, Angew. Chem. Int. Ed. 53(2014) 11716-11754.
doi: 10.1002/anie.201309937
P.A. Gale, N. Busschaert, C.J.E. Haynes, L.E. Karagiannidis, I.L. Kirby, Chem. Soc. Rev. 43(2014) 205-241.
doi: 10.1039/C3CS60316D
L.E. Santos-Figueroa, M.E. Moragues, E. Climent, A. Agostini, Chem. Soc. Rev. 42(2013) 3489-3613.
doi: 10.1039/c3cs35429f
P.A. Gale, E.N.W. Howe, X. Wu, Chem 1(2016) 351-422.
doi: 10.1016/j.chempr.2016.08.004
X. Kan, H. Liu, Q. Pan, Z. Li, Y. Zhao, Chin. Chem. Lett. 29(2018) 261-266.
doi: 10.1016/j.cclet.2017.08.042
S. Kubik, Chem. Soc. Rev. 39(2010) 3648-3663.
doi: 10.1039/b926166b
J. Liu, Q. Lin, H. Yao, et al., Chin. Chem. Lett. 25(2014) 35-38.
doi: 10.1016/j.cclet.2013.10.026
Y. Li, A.H. Flood, Angew. Chem. Int. Ed. 47(2008) 2649-2652.
Y. Li, A.H. Flood, J. Am. Chem. Soc. 130(2008) 12111-12122.
doi: 10.1021/ja803341y
Y. Hua, R.O. Ramabhadran, E.O. Uduehi, et al., Chem.-Eur. J. 17(2011) 312-321.
doi: 10.1002/chem.201002340
R.K. Chhatra, A. Kumar, P.S. Pandey, J. Org. Chem. 76(2011) 9086-9089.
doi: 10.1021/jo201161n
W. Li, Q. Xu, Y. Li, et al., Tetrahedron Lett. 54(2013) 3868-3871.
doi: 10.1016/j.tetlet.2013.05.031
D. Mungalpara, S. Stegmüller, S. Kubik, Chem. Commun. 53(2017) 5095-5098.
doi: 10.1039/C7CC02424J
Y. Zhao, Y. Li, Y. Li, et al., Org. Biomol. Chem. 8(2010) 3923-3927.
doi: 10.1039/c0ob00033g
L.C. Gilday, N.G. White, P.D. Beer, Dalton Trans. 41(2012) 7092-7097.
doi: 10.1039/c2dt30124e
M.G. Fisher, P.A. Gale, J.R. Hiscock, et al., Chem. Commun. (2009) 3017-3019.
T. Merckx, C.J.E. Haynes, L.E. Karagiannidis, et al., Org. Biomol. Chem. 13(2015) 1654-1661.
doi: 10.1039/C4OB02236J
M. Caricato, A. Olmo, C. Gargiulli, G. Gattuso, D. Pasini, Tetrahedron 68(2012) 7861-7866.
doi: 10.1016/j.tet.2012.07.038
K.M. Mullen, J. Mercurio, C.J. Serpell, P.D. Beer, Angew. Chem. Int. Ed. 48(2009) 4781-4784.
doi: 10.1002/anie.v48:26
G.T. Spence, M.B. Pitak, P.D. Beer, Chem.-Eur. J. 18(2012) 7100-7108.
doi: 10.1002/chem.201200317
S.W. Robinson, C.L. Mustoe, N.G. White, et al., J. Am. Chem. Soc.137(2015) 499-507.
doi: 10.1021/ja511648d
J.M. Mercurio, A. Caballero, J. Cookson, P.D. Beer, RSC Adv. 5(2015) 9298-9306.
doi: 10.1039/C4RA15380D
J.Y.C. Lim, I. Marques, A.L. Thompson, et al., J. Am. Chem. Soc. 139(2017) 3122-3133.
doi: 10.1021/jacs.6b12745
T.A. Barendt, L. Ferreira, I. Marques, V. Félix, P.D. Beer, J. Am. Chem. Soc. 139(2017) 9026-9037.
doi: 10.1021/jacs.7b04295
J.L. Sessler, J. Cai, H.Y. Gong, et al., J. Am. Chem. Soc. 132(2010) 14058-14060.
doi: 10.1021/ja107098r
J. Cai, B.P. Hay, N.J. Young, X. Yang, J.L. Sessler, Chem. Sci. 4(2013) 1560-1567.
doi: 10.1039/c3sc22144j
Q. Duan, W. Xia, C. Lin, Y. Pan, L. Wang, Tetrahedron Lett. 56(2015) 4002-4006.
doi: 10.1016/j.tetlet.2015.05.013
Y.H. Zhang, H. Huang, S.S. Yang, Q.Y. Cao, J. Organomet. Chem. 871(2018) 74-78.
doi: 10.1016/j.jorganchem.2018.07.009
C.T. Li, Q.Y. Cao, J.J. Li, Z.W. Wang, B.N. Dai, Inorg. Chim. Acta 449(2016) 31-37.
doi: 10.1016/j.ica.2016.04.047
R. Jiang, Y. Li, Z. Qin, et al., RSC Adv. 4(2014) 2023-2028.
doi: 10.1039/C3RA46049E
N.G. White, S. Carvalho, V. Félix, P.D. Beer, Org. Biomol. Chem. 10(2012) 6951-6959.
doi: 10.1039/c2ob25934f
H.M. Kim, B.R. Cho, Acc. Chem. Res. 42(2009) 863-872.
doi: 10.1021/ar800185u
F.L. Que, C.J. Chang, Chem. Soc. Rev. 39(2010) 51-60.
doi: 10.1039/B914348N
C.J. Chang, Acc. Chem. Res. 50(2017) 535-538.
doi: 10.1021/acs.accounts.6b00531
B. Schulze, U.S. Schubert, Chem. Soc. Rev. 43(2014) 2522-2571.
doi: 10.1039/c3cs60386e
Y.W. Wang, Y.X. Hua, H.H. Wu, X. Sun, Y. Peng, Chin. Chem. Lett. 28(2017) 1994-1996.
doi: 10.1016/j.cclet.2017.07.019
M. Song, Z. Sun, C. Han, et al., Chem. Asian J. 9(2004) 2344-2357.
J. Hu, J. Wu, J. Lu, Y. Ju, Tetrahedron Lett. 53(2012) 6705-6709.
doi: 10.1016/j.tetlet.2012.09.118
J. Wu, J. Lu, J. Liu, et al., Sens. Actuators B Chem. 241(2017) 931-937.
doi: 10.1016/j.snb.2016.10.117
M.K. Jaiswal, P.K. Muwal, S. Pandey, P.S. Pandey, Tetrahedron Lett. 58(2017) 2153-2156.
doi: 10.1016/j.tetlet.2017.04.067
B.N. Dai, Q.Y. Cao, L. Wang, Z.C. Wang, Z. Yang, Inorg. Chim. Acta 423(2014) 163-167.
doi: 10.1016/j.ica.2014.08.015
W. Zhu, X. Lü, J. Zhu, Q. Cao, Chin. J. Org. Chem. 37(2017) 624-629.
doi: 10.6023/cjoc201611004
S. Rahman, Y. Assiri, A.N. Alodhayb, et al., New J. Chem. 40(2016) 434-440.
doi: 10.1039/C5NJ01362C
M.D. Aljabri, S. Rahman, P.E. Georghiou, R. Shofiur, ChemistrySelect 2(2017) 1214-1218.
doi: 10.1002/slct.201601923
Z. Zhang, C. Deng, Y. Zou, L. Chen, J. Photochem. Photobiol. A:Chem. 356(2018) 7-17.
doi: 10.1016/j.jphotochem.2017.12.023
Y.C. Hsieh, J.L. Chir, H.H. Wu, C.Q. Guo, A.T. Wu, Tetrahedron Lett. 51(2010) 109-111.
doi: 10.1016/j.tetlet.2009.10.093
S.T. Yang, D.J. Liao, S.J. Chen, C.H. Hu, A.T. Wu, Analyst 137(2012) 1553-1555.
doi: 10.1039/c2an16315b
F. Miao, J. Zhou, D. Tian, H. Li, Org. Lett. 14(2012) 3572-3575.
doi: 10.1021/ol3007919
B. Khan, M.R. Shah, D. Ahmed, et al., J. Hazard. Mater. 309(2016) 97-106.
doi: 10.1016/j.jhazmat.2016.01.074
S.H. Kim, H.S. Choi, J. Kim, et al., Org. Lett. 12(2010) 560-563.
doi: 10.1021/ol902743s
J.T. Hou, Q.F. Zhang, B.Y. Xu, et al., Tetrahedron Lett. 52(2011) 4927-4930.
doi: 10.1016/j.tetlet.2011.07.050
Z. Wang, B. Dai, J. Qiu, Q. Cao, J. Ge, Chin. J. Org. Chem. 35(2015) 2383-2388.
doi: 10.6023/cjoc201506021
Y. Yu, Y. Li, S. Chen, et al., Eur. J. Org. Chem. (2012) 4287-4292.
S.C. Picot, B.R. Mullaney, P.D. Beer, Chem.-Eur. J. 18(2012) 6230-6237.
doi: 10.1002/chem.201200251
B. Qiao, A. Sengupta, Y. Liu, et al., J. Am. Chem. Soc. 137(2015) 9746-9757.
doi: 10.1021/jacs.5b05839
R. Tepper, B. Schulze, P. Bellstedt, et al., Chem. Commun. 53(2017) 2260-2263.
doi: 10.1039/C6CC09749A
J. Samanta, R. Natarajan, Org. Lett. 18(2016) 3394-3397.
doi: 10.1021/acs.orglett.6b01554
I.S. Tamgho, S. Chaudhuri, M. Verderame, D.J. DiScenza, M. Levine, RSC Adv. 7(2017) 28489-28493.
doi: 10.1039/C7RA05404A
A. Ghorai, E. Padmanaban, C. Mukhopadhyay, B. Achari, P. Chattopadhyay, Chem. Commun. 48(2012) 11975-11977.
doi: 10.1039/c2cc36566a
V. Haridas, A.R. Sapala, J.P. Jasinski, Chem. Commun. 51(2015) 6905-6908.
doi: 10.1039/C4CC09587A
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