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 shu

High-yield synthesis of a novel water-soluble macrocycle for selective recognition of naphthalene

    * Corresponding author.
    E-mail address: zengfei@iccas.ac.cn (F. Zeng).
  • Received Date: 27 September 2020
    Revised Date: 3 November 2020
    Accepted Date: 10 November 2020
    Available Online: 10 November 2020

Figures(5)

  • A novel good water-soluble macrocycle containing two pyridinium moieties was synthesized in high yield. It could form 1:1 complexes with neutral guests containing naphthalene or phenyl units in water. The water-soluble macrocycle can selectively encapsulate naphthalene to form a 1:1 complex over a variety of polycyclic aromatic hydrocarbons.
  • Efficient synthesis of novel macrocyclic hosts with unique structures and good host–guest properties is a permanent and challenging topic in the field of supramolecular chemistry [1-7]. During the last decade, considerable effort has been devoted to the development of macrocyclic molecular and a number of new macrocyclic receptors with novel properties have been reported, such as heterocalix[n]aromatics [8-10], pillar[n]arene [11-16], helicarenes [17-19], naphthotubes [20-24], Ex-box and Ex-cage [25-32], and others [33-37]. However, most of the reported macrocyclic hosts showed poor solubility and weak host–guest interactions in water. To develop a new macrocyclic molecule with good water solubility and molecular recognition properties not only helps us to understand and mimic the biological processes, but also enriches the toolbox of supramolecular chemists. Water soluble groups including sulfonate [38-40], carboxylate [41-43] and quaternary amine groups [44, 45] have been modified onto the macrocyclic hosts to increase their water solubility. These approaches often suffer from long synthetic steps and low yields, which restrict their further application in the complicated supramolecular self-assembly. Undoubtedly, it is important to develop novel water-soluble macrocyclic hosts that could be obtained in high yields and show good host–guest properties in water. Recently, Li and coworkers [46, 47] reported the efficient synthesis of water-soluble macrocyclic hosts using dynamic covalent chemistry (DCC) approach. In their method, both macrocycles and [2] catenanes could be obtained in high yields under the thermodynamic control. However, the purification of [2] catenanes need chromatographic. Previously, our group [42, 43] prepared a novel water-soluble cylindrical macrotricyclic host, and found that the host could bind two N-methylquinolinium salts to form 1:2 complexes in water. Inspired by these results, we deduced that whether we could find a new strategy to construct novel water-soluble macrocyclic host with significant host–guest properties in high yields.

    So far as we know, 1, 8-bis(4-pyridylethynyl)anthracene, which looks like a molecule "clip", has been used as donor building block to prepare trigonal prisms [48]. Thus, the anthracene-based "clip" could also serve as half part of a macrocycle and a macrocyclic host could be obtained when a suitable building block was introduced to this clip. Herein, we report the efficient synthesis of a novel water soluble macrocyclic host 12+·2Br and its complexation with neutral guests in water. By the utilization of the anthracene-based "clip" to react with 1, 4-bis(bromomethyl)benzene, host 12+·2Br can be obtain via simple filtration in a high yield of 82%. Moreover, it was found that host 12+·2Br could form 1:1 complexes with guests 2 and 3 in water solution (Fig. 1). Interestingly, we discovered that host 12+·2Br could only selectively accommodate naphthalene among a variety of polycyclic aromatic hydrocarbons in water. This selective host-guest recognition could be employed for the further removal of naphthalene from sewage.

    Figure 1

    Figure 1.  Structures and the proton designations of host 12+·2Br, guests 2 and 3.

    Synthesis of host 12+·2Br was outlined in Scheme 1. Compound 4 was first prepared according to the literature procedure [48]. By the reaction of 4 and commercially available 1, 4-bis(bromomethyl)benzene in acetonitrile at 90 ℃, host 12+·2Br could be easily synthesized in 82% yield. Macrocyclic host 12+·2Br showed moderate solubility in water, and its structure was confirmed by 1H NMR, 13C NMR, HRMS spectra and crystal structure analysis (Supporting information).

    Scheme 1

    Scheme 1.  Synthesis of host 12+·2Br.

    Firstly, the binding properties of host 12+·2Br toward neutral guests 2 and 3 were investigated by 1H NMR spectra in water solution. Unlike the previous results that reported by our group [43], after electron-poor host 12+·2Br (4.0 mmol/L) and electron-rich guest 2 with 1:1 molar ratio were mixed in water, no obviously color change was observed. The similar phenomenon was also observed for the aqueous solution between host 12+·2Br and guests 3. These results led us to doubt that whether host 12+·2Br could form of complexes with guests 2 and 3. Consequently, the 1H NMR experiments were carried out to further investigate the complexation between host 12+·2Br and guest 2 in water. As shown in Fig. 2, the 1H NMR spectrum of a 1:1 mixture of 12+·2Br and 2 in D2O showed a great difference with those for free host 12+·2Br and free guest 2. Upfield shifts of the resonances of protons H1, H2 and H3 corresponding to guest 2 were observed, which indicated that the naphthalene unit of 2 experienced a shielded magnetic environment in the aromatic cavity of 12+·2Br. Moreover, the signal of protons Hf and Hg in host 12+·2Br also shifted upfield, implying that the electron-poor pyridine unit of 12+·2Br was in shielded magnetic environment and a new complex 1·2 could be formed. Meanwhile, by increasing the amount of guest 2, the spectrum of complex 1·2 showed only one set of resonances, which indicated that the complexation and decomplexation between host 12+·2Br and guest 2 were a fast exchange process on the NMR time scale at room temperature. The formation of complex 1·2 was also supported by 2D NOESY spectral experiment. As shown in the Fig. S4 (Supporting information), the clear correlation signals between protons H1-Hg, H2-Hg and the protons of crown ether units of host 12+·2Br were observed, which was also consistent with the formation of complex 1·2. Moreover, 1H NMR titrations and nonlinear fitting were then performed to quantitatively estimate the 1:1 binding manner between host 12+·2Br and guest 2. Consequently, it was found that 1:1 complex 1·2 were formed by the mole ratio plot. The binding constant (K) of the complex 212+·2Br was calculated to be 184±4 L/mol by the Scatchard plot [49]. By the counteranion exchange of 12+·2Br, we also prepared oil-soluble 12+·2PF6 and investigated its complexation with 2 in MeCN. As shown in Fig. S3 (Supporting information), the 1H NMR spectrum of the 1:1 mixture of 12+·2PF6 and 2 was essentially the sum of the two components, indicating that no obvious complexation between 12+·2PF6 and 2 occurred and the major driving force for the formation of 212+·2Br in water could be hydrophobic interactions. In addition, the binding constant of the complex 312+·2Br was measured to be around 64±2 L/mol in D2O at 298 K. Compared to guest 2 containing a naphthalene unit, guest 3 has a smaller phenyl hydrophobic moiety, which accounted for its lower binding constant within host 12+·2Br.

    Figure 2

    Figure 2.  Partial 1H NMR spectra (400 MHz, D2O, 295 K) of (a) free guest 2, (b) 12+·2Br and 1.0 equiv. of 2, (c) free host 12+·2Br. [12+·2Br]0=4.0 mmol/L.

    The attempts to obtain the single crystal of 212+·2Br and 12+·2Br were unsuccessful. Fortunately, a yellow single crystal of 12+·2PF6 was obtained by slow vapor diffusion of ether to a solution of 12+·2PF6 in CH3CN, providing unambiguous evidence for the formation of 12+·2Br. As shown in Fig. 3a, the two pyridinium residues orientate in a face-to-face nanner and the distance between two N and C atoms of pyridinium residues are measured to be 5.812 Å (h) and 5.647 Å (g), indicating the moderate-sized cavity of host 12+·2PF6. Interestingly, it was found that PF6 ion showed not only multiple CH···F hydrogen bonds but also anion···π interactions with pyridinium rings with the distance of 2.989 (d), 3.062 (e) and 3.159 (f), respectively. Moreover, π···π interaction between two anthracene groups of host 12+·2PF6 with a distance of 3.846 Å (i) was also observed (Fig. 3b). Because of these multiple noncovalent interactions, the macrocyclic molecule 12+·2PF6 could self-assemble to form a 1D tubular channel with PF6 ions inside the channels.

    Figure 3

    Figure 3.  Crystal structure of 12+·2PF6 (a). Crystal structure of self-assembly 12+·2PF6 side view (b), top view (c). Dashed lines denote the noncovalent interactions between the two components. CH···F hydrogen bond distances (Å): a=2.461, b=2.404, c=2.557. PF6 ions and hydrogen atoms not involved in the noncovalent interactions are omitted for clarity.

    Inspired by the formation of complex 1·2 in water, we further investigated the capability of 12+·2Br to accommodate a variety of polycyclic aromatic hydrocarbons in water. As shown in Fig. 4a, 1H NMR spectroscopy revealed that 12+·2Br can encapsulate naphthalene to formation of 1:1 complex. However, the formation of 1:1 complexes between 12+·2Br and anthracene, phenanthrene, triphenylene, pyrene and perylene were not observed (Figs. 4b–f). These observations could be explained by the fact that host 12+·2Br had a small cavity and could only recognize small polycyclic aromatic hydrocarbons such as naphthalene. However, because of the extremely poor solubility of naphthalene in water, the corresponding binding constants of host 12+·2Br and naphthalene could not be determined. The highly selective binding behavior of host 12+·2Br toward naphthalene could be further used for the separation of naphthalene from a variety of polycyclic aromatic hydrocarbons.

    Figure 4

    Figure 4.  Partial 1H NMR spectra (400 MHz, D2O, 298 K) of 12+·2Br after addition of a variety of water-insoluble guests including (a) naphthalene, (b) anthracene, (c) phenanthrene, (d) triphenylene, (e) pyrene and (f) perylene. All the spectra were recorded after sonicating the corresponding suspensions for no less than 24 h to allow the host–guest complexation to reach the equilibrium. The resonance signals of the guests are labelled with red arrows.

    In conclusion, by taking advantage of anthracene-based "clip" structure, we developed an efficient approach to construct a water-soluble macrocycle and studied its binding ability toward neutral guests containing naphthalene or phenyl units in water. The formation of 1:1 complexes between host 12+·2Br and 2 or 3 were confirmed by the 1H NMR titrations experiment. Additionally, we demonstrated that the major driving force for the formation of 212+·2Br or 312+·2Br in water might be hydrophobic interactions. We further investigated its ability to host a variety of polycyclic aromatic hydrocarbons in aqueous solution. It was found that host 12+·2Br could selectively encapsulate of naphthalene to formation of 1:1 complexes over a variety of polycyclic aromatic hydrocarbons. This highly selective accommodation hydrophobic guest in water could be explained by the fact that host 12+·2Br had a relatively small hydrophobic cavity. The application of this novel water-soluble host for the separation of naphthalene from a variety of polycyclic aromatic hydrocarbons and removal of naphthalene from sewage, are underway in our laboratory.

    The authors report no declarations of interest.

    The authors are grateful for the financial support from the National Natural Science Foundation of China (Nos. 21602055 and 51772091); Natural Science Foundation of Hunan Province (No. 2017JJ3094) and Research Foundation of Education Bureau of Hunan Province (No. 18C1072).

    Supplementary material related to this article can be found, in the online version, at doi:https://doi.org/10.1016/j.cclet.2020.11.019.


    * Corresponding author.
    E-mail address: zengfei@iccas.ac.cn (F. Zeng).
    1. [1]

      K. Gloe, Macrocyclic Chemistry: Current Trends and Future Perspectives, Springer, Dordrecht, 2005.

    2. [2]

      F. Davis, S. Higson, Macrocycles: Construction, Chemistry and Nanotechnology Applications, Wiley, Chichester, 2011.

    3. [3]

      J.W. Steed, J.L. Atwood, Supramolecular Chemistry, 2nd ed., Wiley, Chichester, 2009.

    4. [4]

      C.F. Chen, Chem. Commun. 47(2011) 1674-1688.  doi: 10.1039/c0cc04852f

    5. [5]

      T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem. Rev. 116(2016) 7937-8002.  doi: 10.1021/acs.chemrev.5b00765

    6. [6]

      Y. Han, Z. Meng, Y.X. Ma, C.F. Chen, Acc. Chem. Res. 47(2014) 2026-2040.  doi: 10.1021/ar5000677

    7. [7]

      G. Yu, K. Jie, F. Huang, Chem. Rev. 115(2015) 7240-7303.  doi: 10.1021/cr5005315

    8. [8]

      M.X. Wang, Acc. Chem. Res. 45(2012) 182-195.  doi: 10.1021/ar200108c

    9. [9]

      E.X. Zhang, D.X. Wang, Q.Y. Zheng, M.X. Wang, Org. Lett. 10(2008) 2565-2568.  doi: 10.1021/ol800840m

    10. [10]

      R.B. Xu, Q.Q. Wang, Y.F. Ao, et al., Org. Lett. 19(2017) 738-741.  doi: 10.1021/acs.orglett.7b00070

    11. [11]

      T. Ogoshi, S. Kanai, S. Fujinami, T.A. Yamagishi, J. Am. Chem. Soc. 130(2008) 5022-5023.  doi: 10.1021/ja711260m

    12. [12]

      M. Xue, Y. Yang, X.D. Chi, Z.B. Zhang, F. Huang, Acc. Chem. Res. 45(2012) 1294-1308.  doi: 10.1021/ar2003418

    13. [13]

      N.L. Strutt, H. Zhang, S.T. Schneebeli, J.F. Stoddart, Acc. Chem. Res. 47(2014) 2631-2642.  doi: 10.1021/ar500177d

    14. [14]

      H. Chen, J. Fan, X. Hu, et al., Chem. Sci. 6(2015) 197-202.  doi: 10.1039/C4SC02422B

    15. [15]

      J. Ma, H. Deng, S. Ma, et al., Chem. Commun. 51(2015) 6621-6624.  doi: 10.1039/C5CC01470K

    16. [16]

      J. Ye, R. Zhang, W. Yang, et al., Chin. Chem. Lett. 31(2020) 1550-1553.  doi: 10.1016/j.cclet.2019.11.041

    17. [17]

      G.W. Zhang, P.F. Li, Z. Meng, et al., Angew. Chem. Int. Ed. 55(2016) 5304-5308.  doi: 10.1002/anie.201600911

    18. [18]

      Q. Shi, C.F. Chen, Org. Lett. 19(2017) 3175-3178.  doi: 10.1021/acs.orglett.7b01296

    19. [19]

      G.W. Zhang, Y. Han, Y. Wang, C.F. Chen, Chem. Commun. 53(2017) 10433-10436.  doi: 10.1039/C7CC05489K

    20. [20]

      G.B. Huang, S.H. Wang, H. Ke, et al., J. Am. Chem. Soc. 138(2016) 14550-14553.  doi: 10.1021/jacs.6b09472

    21. [21]

      L.L. Wang, Z. Chen, W.E. Liu, et al., J. Am. Chem. Soc. 139(2017) 8436-8439.  doi: 10.1021/jacs.7b05021

    22. [22]

      Y.L. Ma, H. Ke, A. Valkonen, K. Rissanen, W. Jiang, Angew. Chem. Int. Ed. 57(2018) 709-713.  doi: 10.1002/anie.201711077

    23. [23]

      Z. He, G. Ye, W. Jiang, Chem. Eur. J. 21(2015) 3005-3012.  doi: 10.1002/chem.201405912

    24. [24]

      J.S. Cui, Q.K. Ba, H. Ke, et al., Angew. Chem. Int. Ed. 57(2018) 7809-7814.  doi: 10.1002/anie.201803349

    25. [25]

      Z. Liu, S.K.M. Nalluri, J.F. Stoddart, Chem. Soc. Rev. 46(2017) 2459-2478.  doi: 10.1039/C7CS00185A

    26. [26]

      J.C. Barnes, M. Juríček, N.L. Strutt, et al., J. Am. Chem. Soc. 135(2013) 183-192.  doi: 10.1021/ja307360n

    27. [27]

      S.T.J. Ryan, J.D. Barrio, I. Ghosh, et al., J. Am. Chem. Soc. 136(2014) 9053-9060.  doi: 10.1021/ja5032437

    28. [28]

      I. Roy, S. Bobbala, R.M. Young, et al., J. Am. Chem. Soc. 141(2019) 12296-12304.  doi: 10.1021/jacs.9b03990

    29. [29]

      J. Zhou, Y. Wu, I. Roy, et al., Chem. Sci. 10(2019) 4282-4292.  doi: 10.1039/C8SC05514A

    30. [30]

      M. Juríček, J.C. Barnes, N.L. Strutt, et al., Chem. Sci. 5(2014) 2724-2731.  doi: 10.1039/c4sc00488d

    31. [31]

      M. Juríček, J.C. Barnes, E.J. Dale, et al., J. Am. Chem. Soc. 135(2013) 12736-12746.  doi: 10.1021/ja4052763

    32. [32]

      E.J. Dale, N.A. Vermeulen, A.A. Thomas, et al., J. Am. Chem. Soc. 136(2014) 10669-10682.  doi: 10.1021/ja5041557

    33. [33]

      Y. Chen, C. Qian, Q. Zhao, et al., Chem. Commun. 55(2019) 8072-8075.  doi: 10.1039/C9CC03577J

    34. [34]

      M. Cheng, J. Zhang, X. Ren, et al., Chem. Commun. 53(2017) 11838-11841.  doi: 10.1039/C7CC07469G

    35. [35]

      C. Zhang, Z. Wang, L. Tan, et al., Angew. Chem. Int. Ed. 54(2015) 9244-9248.  doi: 10.1002/anie.201502912

    36. [36]

      Z. Wang, Y. Luo, T.L. Zhai, et al., Org. Lett. 18(2016) 4574-4577.  doi: 10.1021/acs.orglett.6b02219

    37. [37]

      C. Zhang, Z. Wang, S. Song, et al., J. Org. Chem. 79(2014) 2729-2732.  doi: 10.1021/jo402884a

    38. [38]

      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

    39. [39]

      L. Chen, Y.M. Zhang, Y. Liu, J. Phys. Chem. B 116(2012) 9500-9506.  doi: 10.1021/jp305503e

    40. [40]

      L. Chen, H.Y. Zhang, Y. Liu, J. Org. Chem. 77(2012) 9766-9773.  doi: 10.1021/jo301911w

    41. [41]

      X. Ji, M. Zhang, X. Yan, J. Li, Chem. Commun. 49(2013) 1178-1180.  doi: 10.1039/c2cc38472h

    42. [42]

      F. Zeng, C.F. Chen, Org. Boimol. Chem. 13(2015) 1988-1991.  doi: 10.1039/C4OB02533D

    43. [43]

      F. Zeng, L.L. Tang, X.M. Chen, et al., J. Org. Chem. 36(2016) 1937-1941.

    44. [44]

      Y. Ma, X. Ji, F. Xiang, et al., Chem. Commun. 47(2011) 12340-12342.  doi: 10.1039/c1cc15660h

    45. [45]

      B. Gómez, V. Francisco, F. Fernández-Nieto, et al., Chem. Eur. J. 20(2014) 12123-12132.  doi: 10.1002/chem.201403194

    46. [46]

      G. Wu, C.Y. Wang, T. Jiao, et al., J. Am. Chem. Soc. 140(2018) 5955-5961.  doi: 10.1021/jacs.8b01651

    47. [47]

      L. Shen, N. Cao, L. Tong, et al., Angew. Chem. Int. Ed. 57(2018) 16486-16490.  doi: 10.1002/anie.201811025

    48. [48]

      Y.K. Kryschenko, S.R. Seidel, D.C. Muddiman, et al., J. Am. Chem. Soc. 125(2003) 9647-9652.  doi: 10.1021/ja030209n

    49. [49]

      K.A. Connors, Binding Constants, J. Wiley and Sons, New York, 1987.

    1. [1]

      K. Gloe, Macrocyclic Chemistry: Current Trends and Future Perspectives, Springer, Dordrecht, 2005.

    2. [2]

      F. Davis, S. Higson, Macrocycles: Construction, Chemistry and Nanotechnology Applications, Wiley, Chichester, 2011.

    3. [3]

      J.W. Steed, J.L. Atwood, Supramolecular Chemistry, 2nd ed., Wiley, Chichester, 2009.

    4. [4]

      C.F. Chen, Chem. Commun. 47(2011) 1674-1688.  doi: 10.1039/c0cc04852f

    5. [5]

      T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem. Rev. 116(2016) 7937-8002.  doi: 10.1021/acs.chemrev.5b00765

    6. [6]

      Y. Han, Z. Meng, Y.X. Ma, C.F. Chen, Acc. Chem. Res. 47(2014) 2026-2040.  doi: 10.1021/ar5000677

    7. [7]

      G. Yu, K. Jie, F. Huang, Chem. Rev. 115(2015) 7240-7303.  doi: 10.1021/cr5005315

    8. [8]

      M.X. Wang, Acc. Chem. Res. 45(2012) 182-195.  doi: 10.1021/ar200108c

    9. [9]

      E.X. Zhang, D.X. Wang, Q.Y. Zheng, M.X. Wang, Org. Lett. 10(2008) 2565-2568.  doi: 10.1021/ol800840m

    10. [10]

      R.B. Xu, Q.Q. Wang, Y.F. Ao, et al., Org. Lett. 19(2017) 738-741.  doi: 10.1021/acs.orglett.7b00070

    11. [11]

      T. Ogoshi, S. Kanai, S. Fujinami, T.A. Yamagishi, J. Am. Chem. Soc. 130(2008) 5022-5023.  doi: 10.1021/ja711260m

    12. [12]

      M. Xue, Y. Yang, X.D. Chi, Z.B. Zhang, F. Huang, Acc. Chem. Res. 45(2012) 1294-1308.  doi: 10.1021/ar2003418

    13. [13]

      N.L. Strutt, H. Zhang, S.T. Schneebeli, J.F. Stoddart, Acc. Chem. Res. 47(2014) 2631-2642.  doi: 10.1021/ar500177d

    14. [14]

      H. Chen, J. Fan, X. Hu, et al., Chem. Sci. 6(2015) 197-202.  doi: 10.1039/C4SC02422B

    15. [15]

      J. Ma, H. Deng, S. Ma, et al., Chem. Commun. 51(2015) 6621-6624.  doi: 10.1039/C5CC01470K

    16. [16]

      J. Ye, R. Zhang, W. Yang, et al., Chin. Chem. Lett. 31(2020) 1550-1553.  doi: 10.1016/j.cclet.2019.11.041

    17. [17]

      G.W. Zhang, P.F. Li, Z. Meng, et al., Angew. Chem. Int. Ed. 55(2016) 5304-5308.  doi: 10.1002/anie.201600911

    18. [18]

      Q. Shi, C.F. Chen, Org. Lett. 19(2017) 3175-3178.  doi: 10.1021/acs.orglett.7b01296

    19. [19]

      G.W. Zhang, Y. Han, Y. Wang, C.F. Chen, Chem. Commun. 53(2017) 10433-10436.  doi: 10.1039/C7CC05489K

    20. [20]

      G.B. Huang, S.H. Wang, H. Ke, et al., J. Am. Chem. Soc. 138(2016) 14550-14553.  doi: 10.1021/jacs.6b09472

    21. [21]

      L.L. Wang, Z. Chen, W.E. Liu, et al., J. Am. Chem. Soc. 139(2017) 8436-8439.  doi: 10.1021/jacs.7b05021

    22. [22]

      Y.L. Ma, H. Ke, A. Valkonen, K. Rissanen, W. Jiang, Angew. Chem. Int. Ed. 57(2018) 709-713.  doi: 10.1002/anie.201711077

    23. [23]

      Z. He, G. Ye, W. Jiang, Chem. Eur. J. 21(2015) 3005-3012.  doi: 10.1002/chem.201405912

    24. [24]

      J.S. Cui, Q.K. Ba, H. Ke, et al., Angew. Chem. Int. Ed. 57(2018) 7809-7814.  doi: 10.1002/anie.201803349

    25. [25]

      Z. Liu, S.K.M. Nalluri, J.F. Stoddart, Chem. Soc. Rev. 46(2017) 2459-2478.  doi: 10.1039/C7CS00185A

    26. [26]

      J.C. Barnes, M. Juríček, N.L. Strutt, et al., J. Am. Chem. Soc. 135(2013) 183-192.  doi: 10.1021/ja307360n

    27. [27]

      S.T.J. Ryan, J.D. Barrio, I. Ghosh, et al., J. Am. Chem. Soc. 136(2014) 9053-9060.  doi: 10.1021/ja5032437

    28. [28]

      I. Roy, S. Bobbala, R.M. Young, et al., J. Am. Chem. Soc. 141(2019) 12296-12304.  doi: 10.1021/jacs.9b03990

    29. [29]

      J. Zhou, Y. Wu, I. Roy, et al., Chem. Sci. 10(2019) 4282-4292.  doi: 10.1039/C8SC05514A

    30. [30]

      M. Juríček, J.C. Barnes, N.L. Strutt, et al., Chem. Sci. 5(2014) 2724-2731.  doi: 10.1039/c4sc00488d

    31. [31]

      M. Juríček, J.C. Barnes, E.J. Dale, et al., J. Am. Chem. Soc. 135(2013) 12736-12746.  doi: 10.1021/ja4052763

    32. [32]

      E.J. Dale, N.A. Vermeulen, A.A. Thomas, et al., J. Am. Chem. Soc. 136(2014) 10669-10682.  doi: 10.1021/ja5041557

    33. [33]

      Y. Chen, C. Qian, Q. Zhao, et al., Chem. Commun. 55(2019) 8072-8075.  doi: 10.1039/C9CC03577J

    34. [34]

      M. Cheng, J. Zhang, X. Ren, et al., Chem. Commun. 53(2017) 11838-11841.  doi: 10.1039/C7CC07469G

    35. [35]

      C. Zhang, Z. Wang, L. Tan, et al., Angew. Chem. Int. Ed. 54(2015) 9244-9248.  doi: 10.1002/anie.201502912

    36. [36]

      Z. Wang, Y. Luo, T.L. Zhai, et al., Org. Lett. 18(2016) 4574-4577.  doi: 10.1021/acs.orglett.6b02219

    37. [37]

      C. Zhang, Z. Wang, S. Song, et al., J. Org. Chem. 79(2014) 2729-2732.  doi: 10.1021/jo402884a

    38. [38]

      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

    39. [39]

      L. Chen, Y.M. Zhang, Y. Liu, J. Phys. Chem. B 116(2012) 9500-9506.  doi: 10.1021/jp305503e

    40. [40]

      L. Chen, H.Y. Zhang, Y. Liu, J. Org. Chem. 77(2012) 9766-9773.  doi: 10.1021/jo301911w

    41. [41]

      X. Ji, M. Zhang, X. Yan, J. Li, Chem. Commun. 49(2013) 1178-1180.  doi: 10.1039/c2cc38472h

    42. [42]

      F. Zeng, C.F. Chen, Org. Boimol. Chem. 13(2015) 1988-1991.  doi: 10.1039/C4OB02533D

    43. [43]

      F. Zeng, L.L. Tang, X.M. Chen, et al., J. Org. Chem. 36(2016) 1937-1941.

    44. [44]

      Y. Ma, X. Ji, F. Xiang, et al., Chem. Commun. 47(2011) 12340-12342.  doi: 10.1039/c1cc15660h

    45. [45]

      B. Gómez, V. Francisco, F. Fernández-Nieto, et al., Chem. Eur. J. 20(2014) 12123-12132.  doi: 10.1002/chem.201403194

    46. [46]

      G. Wu, C.Y. Wang, T. Jiao, et al., J. Am. Chem. Soc. 140(2018) 5955-5961.  doi: 10.1021/jacs.8b01651

    47. [47]

      L. Shen, N. Cao, L. Tong, et al., Angew. Chem. Int. Ed. 57(2018) 16486-16490.  doi: 10.1002/anie.201811025

    48. [48]

      Y.K. Kryschenko, S.R. Seidel, D.C. Muddiman, et al., J. Am. Chem. Soc. 125(2003) 9647-9652.  doi: 10.1021/ja030209n

    49. [49]

      K.A. Connors, Binding Constants, J. Wiley and Sons, New York, 1987.

  • 加载中
    1. [1]

      Shuo LiQianfa LiuLijun MaoXin ZhangChunju LiDa Ma . Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine. Chinese Chemical Letters, 2024, 35(11): 109791-. doi: 10.1016/j.cclet.2024.109791

    2. [2]

      Qihan LinJiabin XingYue-Yang LiuGang WuShi-Jia LiuHui WangWei ZhouZhan-Ting LiDan-Wei ZhangtaBOX: A water-soluble tetraanionic rectangular molecular container for conjugated molecules and taste masking for berberine and palmatine. Chinese Chemical Letters, 2024, 35(5): 109119-. doi: 10.1016/j.cclet.2023.109119

    3. [3]

      Conghui WangLei XuZhenhua JiaTeck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075

    4. [4]

      Zhe LiPing-Zhao LiangLi XuFei-Yu YangTian-Bing RenLin YuanXia YinXiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190

    5. [5]

      Cheng-Da ZhaoHuan YaoShi-Yao LiFangfang DuLi-Li WangLiu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879

    6. [6]

      Zhimin SunXin-Hui GuoYue ZhaoQing-Yu MengLi-Juan XingHe-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162

    7. [7]

      Kai AnQinglong QiaoLoveleshSyed Ali Abbas AbediXiaogang LiuZhaochao Xu . "Superimposed" spectral characteristics of fluorophores arising from cross-conjugation hybridization. Chinese Chemical Letters, 2025, 36(1): 109786-. doi: 10.1016/j.cclet.2024.109786

    8. [8]

      Rui WangYang LiangJulius Rebek Jr.Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228

    9. [9]

      Jie YangXin-Yue LouDihua DaiJingwei ShiYing-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818

    10. [10]

      Chao ZhangAi-Feng LiuShihui LiFang-Yuan ChenJun-Tao ZhangFang-Xing ZengHui-Chuan FengPing WangWen-Chao GengChuan-Rui MaDong-Sheng Guo . A supramolecular formulation of icariin@sulfonatoazocalixarene for hypoxia-targeted osteoarthritis therapy. Chinese Chemical Letters, 2025, 36(1): 109752-. doi: 10.1016/j.cclet.2024.109752

    11. [11]

      Zhenzhu WangChenglong LiuYunpeng GeWencan LiChenyang ZhangBing YangShizhong MaoZeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127

    12. [12]

      Xuanyu WangZhao GaoWei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757

    13. [13]

      Kun ZhangXin-Yue LouYan WangWeiwei HuanYing-Wei Yang . Emission enhancement induced by the supramolecular assembly of leggero pillar[5]arenes for the detection and separation of silver ions. Chinese Chemical Letters, 2025, 36(6): 110464-. doi: 10.1016/j.cclet.2024.110464

    14. [14]

      Shengyong LiuHui LiWei ZhangYan ZhangYan DongWei Tian . Multiple host-guest and metal coordination interactions induce supramolecular assembly and structural transition. Chinese Chemical Letters, 2025, 36(6): 110465-. doi: 10.1016/j.cclet.2024.110465

    15. [15]

      Ying-Mei ZhongZi-Jun XiaYu-Hang HuLi-Peng ZhouLi-Xuan CaiQing-Fu Sun . Effective separation of phenanthrene from isomeric anthracene using a water-soluble macrocycle-based cage. Chinese Chemical Letters, 2025, 36(4): 110164-. doi: 10.1016/j.cclet.2024.110164

    16. [16]

      Kang WeiJiayu LiWen ZhangBing YuanMing-De LiPingwu Du . A strained π-extended [10]cycloparaphenylene carbon nanoring. Chinese Chemical Letters, 2024, 35(5): 109055-. doi: 10.1016/j.cclet.2023.109055

    17. [17]

      Junying ZhangRuochen LiHaihua WangWenbing KangXing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216

    18. [18]

      Zixi ZouJingyuan WangYian SunQian WangDa-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972

    19. [19]

      Zhengzhong ZhuShaojun HuZhi LiuLipeng ZhouChongbin TianQingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641

    20. [20]

      Jingyu ChenSha WuYuhao WangJiong Zhou . Near-perfect separation of alicyclic ketones and alicyclic alcohols by nonporous adaptive crystals of perethylated pillar[5]arene and pillar[6]arene. Chinese Chemical Letters, 2025, 36(4): 110102-. doi: 10.1016/j.cclet.2024.110102

Metrics
  • PDF Downloads(7)
  • Abstract views(1029)
  • HTML views(101)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return