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| Our expedition in the construction of fluorescent supramolecular metallacycles |
| Junlong Zhua, Xi Liua, Junhai Huangb, Lin Xua,c |
a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China;
b Zhangjiang Institute, China State Institute of Pharmaceutical Industry, Shanghai 201203, China;
c State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China |
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| Guide This review summarized our efforts in the development of fluorescent supramolecular metallacycles. |
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Abstract During the past few years, the construction of fluorescent supramolecular metallocycles has attracted extensive attention due to their diverse applications such as sensing, photoelectric devices, and mimicking complicated natural photo-processes. In this review, we will discuss how we entered the field of fluorescent supramolecular metallacycles and what we investigated in this field. The preparation of various fluorescent supramolecular metallacycles and their applications in monitoring the dynamics of coordination-driven self-assembly, sensing, catalysts, and supramolecular gels will be summarized.
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Received: 12 July 2019
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| Fund: Thanks to all excellent authors whose names appear in the references. We acknowledge the National Natural Science Foundation of China (Nos. 21871092 and 21672070), Shanghai Pujiang Program (No. 18PJD015), and the State Key Laboratory of Fine Chemicals (No. KF1801) for the financial support. |
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Corresponding Authors:
Lin Xu
E-mail: lxu@chem.ecnu.edu.cn
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|
| [1] |
Z. Xu, L. Xu, J. Zhou, et al., Chem. Commun. 48(2012) 10871-10873.
|
| [2] |
H.I. Un, S. Wu, C.B. Huang, Z. Xu, L. Xu, Chem. Commun. 51(2015) 3143-3146.
|
| [3] |
Z. Xu, L. Xu, Chem. Commun. 52(2016) 1094-1119.
|
| [4] |
J.L. Zhu, Z. Xu, Y. Yang, L. Xu, Chem. Commun. 55(2019) 6629-6671.
|
| [5] |
L. Xu, Y.X. Wang, H.B. Yang, Dalton Trans. 44(2015) 867-890.
|
| [6] |
P.J. Stang, B. Olenyuk, Acc. Chem. Res. 30(1997) 502-518.
|
| [7] |
D. Fiedler, D.H. Leung, R.G. Bergman, K.N. Raymond, Acc. Chem. Res. 38(2005) 349-358.
|
| [8] |
M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 38(2005) 369-378.
|
| [9] |
S. Liu, Y.F. Han, G.X. Jin, Chem. Soc. Rev. 36(2007) 1543-1560.
|
| [10] |
C.G. Oliver, P.A. Ulman, M.J. Wiester, C.A. Mirkin, Acc. Chem. Res. 41(2008) 1618-1629.
|
| [11] |
B.H. Northrop, Y.R. Zheng, K.W. Chi, P.J. Stang, Acc. Chem. Res. 42(2009) 1554-1563.
|
| [12] |
P. Thanasekaran, R.T. Liao, Y.H. Liu, et al., Coord. Chem. Rev. 249(2005) 1085-1110.
|
| [13] |
M.J. Prakash, M.S. Lah, Chem. Commun. (2009) 3326-3341.
|
| [14] |
S.L. James, Chem. Soc. Rev. 38(2009) 1744-1758.
|
| [15] |
M. Fujita, J. Yazaki, K. Ogura, J. Am. Chem. Soc. 112(1990) 5645-5647.
|
| [16] |
P.J. Stang, D.H. Cao, J. Am. Chem. Soc. 116(1994) 4981-4982.
|
| [17] |
N.C. Gianneschi, M.S. Masar, C.A. Mirkin, Acc. Chem. Res. 38(2005) 825-837.
|
| [18] |
Y.T. Chan, X. Li, M. Soler, et al., J. Am. Chem. Soc. 131(2009) 16395-16397.
|
| [19] |
S.L. Huang, Y.J. Lin, T.S.A. Hor, G.X. Jin, J. Am. Chem. Soc. 135(2013) 8125-8128.
|
| [20] |
A. Mishra, Y.J. Jeong, J.H. Jo, et al., Organometallics 33(2014) 1144-1151.
|
| [21] |
G.H. Ning, L.Y. Yao, L.X. Liu, et al., Inorg. Chem. 49(2010) 7783-7792.
|
| [22] |
C.C. You, F. Würthner, J. Am. Chem. Soc. 125(2003) 9716-9725.
|
| [23] |
J. Stahl, W. Mohr, L. de Quadras, et al., J. Am. Chem. Soc. 129(2007) 8282-8295.
|
| [24] |
G.S. Papaefstathiou, Z. Zhong, L. Gang, L.R. MacGillivray, J. Am. Chem. Soc. 126(2004) 9158-9159.
|
| [25] |
S. Shanmugaraju, S.A. Joshi, P.S. Mukherjee, Inorg. Chem. 50(2011) 11736-11745.
|
| [26] |
S. Shanmugaraju, A.K. Bar, K.W. Chi, P.S. Mukherjee, Organometallics 29(2010) 2971-2980.
|
| [27] |
V. Vajpayee, Y.H. Song, M.H. Lee, et al., Chem.-Eur. J. 17(2011) 7837-7844.
|
| [28] |
S. Ghosh, R. Chakrabarty, P.S. Mukherjee, Inorg. Chem. 48(2009) 549-556.
|
| [29] |
S. Shanmugaraju, V. Vajpayee, S. Lee, et al., Inorg. Chem. 51(2012) 4817-4823.
|
| [30] |
F. Würthner, A. Sautter, Org. Biomol. Chem. 1(2003) 240-243.
|
| [31] |
X. Yan, H. Wang, C.E. Hauke, et al., J. Am. Chem. Soc. 137(2015) 15276-15286.
|
| [32] |
L.J. Chen, Y.Y. Ren, N.W. Wu, et al., J. Am. Chem. Soc. 137(2015) 11725-11735.
|
| [33] |
Y. Tian, X. Yan, M.L. Saha, Z. Niu, P.J. Stang, J. Am. Chem. Soc.138(2016) 12033-12036.
|
| [34] |
N. Thakur, M.D. Pandey, R. Pandey, New J. Chem. 42(2018) 3582-3592.
|
| [35] |
Z. Li, X. Yan, F. Huang, H. Sepehrpour, P.J. Stang, Org. Lett.19(2017) 5728-5731.
|
| [36] |
L. Wang, L.J. Chen, J.Q. Ma, et al., J. Organomet. Chem. 823(2016) 1-7.
|
| [37] |
L. Xu, H.B. Yang, Chem. Rec. 16(2016) 1274-1297.
|
| [38] |
J. Zhang, N.W. Wu, X.D. Xu, et al., RSC Adv. 4(2014) 16047-16054.
|
| [39] |
J.K. Ouyang, L.J. Chen, L. Xu, C.H. Wang, H.B. Yang, Chin. Chem. Lett. 24(2013) 471-474.
|
| [40] |
Y.X. Hu, X. Zhang, L. Xu, H.B. Yang, Isr. J. Chem. 59(2019) 184-196.
|
| [41] |
N.W. Wu, J. Zhang, X.D. Xu, H.B. Yang, Chem. Commun. 50(2014) 10269-10272.
|
| [42] |
Z.Y. Li, L. Xu, C.H. Wang, X.L. Zhao, H.B. Yang, Chem. Commun. 49(2013) 6194-6196.
|
| [43] |
X.D. Xu, J. Zhang, X. Yu, et al., Chem.-Eur. J. 18(2012) 16000-16013.
|
| [44] |
C.B. Huang, L.J. Chen, J. Huang, L. Xu, RSC Adv. 4(2014) 19538-19549.
|
| [45] |
J. Zhang, N.W. Wu, X.D. Xu, et al., RSC Adv. 4(2014) 16047-16054.
|
| [46] |
B. Shi, Y. Liu, H. Zhu, et al., J. Am. Chem. Soc. 141(2019) 6494-6498.
|
| [47] |
N.W. Wu, J. Zhang, C.H. Wang, L. Xu, H.B. Yang, Monatsh. Chem. 144(2013) 553-566.
|
| [48] |
N.W. Wu, J. Zhang, D. Ciren, et al., Organometallics 32(2013) 2536-2545.
|
| [49] |
Y. Qin, L.J. Chen, F. Dong, et al., J. Am. Chem. Soc. 141(2019) 8943-8950.
|
| [50] |
M. Li, L.J. Chen, Y. Cai, et al., Chem 5(2019) 634-648.
|
| [51] |
M. Han, Y. Luo, B. Damaschke, et al., Angew. Chem. Int. Ed. 55(2016) 445-449.
|
| [52] |
Y. Cai, Z. Guo, J. Chen, et al., J. Am. Chem. Soc. 138(2016) 2219-2224.
|
| [53] |
D.H. Qu, Q.C. Wang, Q.W. Zhang, X. Ma, H. Tian, Chem. Rev. 115(2015) 7543-7588.
|
| [54] |
Y. Qin, Y. Zhang, G. Yin, et al., Chin. J. Chem. 37(2019) 323-329.
|
| [55] |
J. Li, A.C. Grimsdale, Chem. Soc. Rev. 39(2010) 2399-2410.
|
| [56] |
A.W. Schmidt, K.R. Reddy, H.J. Knçlker, Chem. Rev. 112(2012) 3193-3328.
|
| [57] |
N. Blouin, M. Leclerc, Acc. Chem. Res. 41(2008) 1110-1119.
|
| [58] |
Y. Wang, B. Chen, W. Wu, et al., Angew. Chem. Int. Ed. 53(2014) 10779-11078.
|
| [59] |
S. Xu, T. Liu, Y. Mu, et al., Angew. Chem. Int. Ed. 53(2014) 1-6.
|
| [60] |
K.R. Wee, W.S. Han, D.W. Cho, et al., Angew. Chem. Int. Ed. 51(2012) 2677-2680.
|
| [61] |
D. Kim, V. Coropceanu, J.L. Brédas, J. Am. Chem. Soc. 133(2011) 17895-17900.
|
| [62] |
G.R. Newkome, C.N. Moorefield, F. Vçgtle, Dendrimers and Dendrons:Concepts, Syntheses, Applications, Wiley-VCH, New York, 2001.
|
| [63] |
C.N. Moorefield, S. Perera, G.R. Newkome, Dendrimer Chemistry:Supramolecular Perspectives and Applications, Wiley, Hoboken, 2012.
|
| [64] |
A.W. Bosman, H.M. Janssen, E.W. Meijer, Chem. Rev. 99(1999) 1665-1688.
|
| [65] |
H.J. Sun, S. Zhang, V. Percec, Chem. Soc. Rev. 44(2015) 3900-3923.
|
| [66] |
R. van Heerbeek, P.C.J. Kamer, P.W.N.M. van Leeuwen, J.N.H. Reek, Chem. Rev. 102(2002) 3717-3756.
|
| [67] |
X.Q. Wang, W. Wang, W.J. Li, et al., Nat. Commun. 9(2018) 3190-3200.
|
| [68] |
W. Wang, L.J. Chen, X.Q. Wang, et al., Proc. Natl. Acad. Sci. U. S. A. 112(2015) 5597-5601.
|
| [69] |
Y.X. Wang, Q.F. Zhou, L.J. Chen, et al., Chem. Commun. 54(2018) 2224-2227.
|
| [70] |
W.J. Fan, B. Sun, J. Ma, et al., Chem.-Eur. J. 21(2015) 12947-12959.
|
| [71] |
M. He, Q. Han, J. He, et al., Chin. J. Chem. 31(2013) 663-672.
|
| [72] |
W. Zheng, W. Wang, S.T. Jiang, et al., J. Am. Chem. Soc. 141(2019) 583-591.
|
| [73] |
L.J. Chen, H.B. Yang, Acc. Chem. Res. 51(2018) 2699-2710.
|
| [74] |
G.Y. Wu, L.J. Chen, L. Xu, X. Zhao, H.B. Yang, Coord. Chem. Rev. 369(2018) 39-75.
|
| [75] |
L.J. Chen, H.B. Yang, M. Shionoya, Chem. Soc. Rev. 46(2017) 2555-2576.
|
| [76] |
B. Jiang, J. Zhang, J.Q. Ma, et al., J. Am. Chem. Soc. 138(2016) 738-741.
|
| [77] |
C.B. Huang, L. Xu, J.L. Zhu, et al., J. Am. Chem. Soc. 139(2017) 9459-9462.
|
| [78] |
L. Zhou, Z. Jin, X. Fan, et al., Chin. Chem. Lett. 29(2018) 1500-1502.
|
| [79] |
X. Sun, Y.W. Wang, Y. Peng, Org. Lett. 14(2012) 3420-3423.
|
| [80] |
Z. Chen, Y. Xu, X. Qian, Chin. Chem. Lett. 29(2018) 1741-1756.
|
| [81] |
H.I. Un, C.B. Huang, J. Huang, et al., Chem.-Asian J. 9(2014) 3397-3402.
|
| [82] |
H.I. Un, C.B. Huang, C. Huang, et al., Org. Chem. Front. 1(2014) 1083-1090.
|
| [83] |
C.B. Huang, H.R. Li, Y. Luo, L. Xu, Dalton Trans. 43(2014) 8102-8108.
|
| [84] |
D. Wu, Y. Shen, J. Chen, et al., Chin. Chem. Lett. 28(2017) 1979-1982.
|
| [85] |
J. Zhu, P. Jia, N. Li, et al., Chin. Chem. Lett. 29(2018) 1445-1450.
|
| [86] |
M.L. He, S. Wu, J. He, Z. Abliz, L. Xu, RSC Adv. 4(2014) 2605-2608.
|
| [87] |
C.B. Huang, J. Huang, L. Xu, RSC Adv. 5(2015) 13307-13310.
|
| [88] |
Z. Xu, Y.Y. Ren, X. Fan, et al., Tetrahedron 71(2015) 5055-5058.
|
| [89] |
L. Xu, M.L. He, H.B. Yang, X. Qian, Dalton Trans. 42(2013) 8218-8222.
|
| [90] |
P. Guo, Q. Chen, T. Liu, et al., ACS Med. Chem. Lett. 4(2013) 527-531.
|
| [91] |
Q. Chen, P. Guo, L. Xu, et al., Biochimie 97(2014) 152-162.
|
| [92] |
Z. Xu, G. Li, Y.Y. Ren, et al., Dalton Trans. 45(2016) 12087-12093.
|
| [93] |
S. De, K. Mahata, M. Schmittel, Chem. Soc. Rev. 39(2010) 1555-1575.
|
| [94] |
M. Fujita, M. Aoyagi, K. Ogura, Inorg. Chim. Acta 246(1996) 53-57.
|
| [95] |
T. Yamamoto, A.M. Arif, P.J. Stang, J. Am. Chem. Soc. 125(2003) 12309-12317.
|
| [96] |
M.L. Saha, X. Yan, P.J. Stang, Acc. Chem. Res. 49(2016) 2527-2539.
|
| [97] |
A. Chowdhury, P. Howlader, P.S. Mukherjee, Chem.-Eur. J. 22(2016) 7468-7478.
|
| [98] |
L.J. Chen, S. Chen, Y. Qin, et al., J. Am. Chem. Soc. 140(2018) 5049-5052.
|
| [99] |
B. Jiang, L.J. Chen, G.Q. Yin, et al., Chem. Commun. 53(2017) 172-175.
|
| [100] |
Y.Y. Ren, N.W. Wu, J. Huang, et al., Chem. Commun. 51(2015) 15153-15156.
|
| [101] |
G.Z. Zhao, L.J. Chen, W. Wang, et al., Chem.-Eur. J. 19(2013) 10094-10100.
|
| [102] |
Z.Y. Li, Y. Zhang, C.W. Zhang, et al., J. Am. Chem. Soc. 136(2014) 8577-8589.
|
| [103] |
N.W. Wu, L.J. Chen, C. Wang, et al., Chem. Commun. 50(2014) 4231-4233.
|
| [104] |
Y.Y. Ren, Z. Xu, G. Li, et al., Dalton Trans. 46(2017) 333-337.
|
| [105] |
C.W. Zhang, B. Ou, S.T. Jiang, et al., Polym. Chem. 9(2018) 2021-2030.
|
|
|
|
