Citation: Yang Luo, Wei Zhang, Qian Ren, Guo-Rong Chen, Jiang-Lian Ran, Xin Xiao. A multiple-function fluorescent pillar[5]arene: Fe³⁺/Ag⁺ detection and light-harvesting system[J]. Chinese Chemical Letters, ;2022, 33(12): 5120-5123. doi: 10.1016/j.cclet.2022.04.028 shu

A multiple-function fluorescent pillar[5]arene: Fe³⁺/Ag⁺ detection and light-harvesting system

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China

gyhxxiaoxin@163.com

Received Date: 8 February 2022
Revised Date: 9 April 2022
Accepted Date: 12 April 2022
Available Online: 15 April 2022

Figures(5)

A novel pillar[5]arene (P5DPB) that includes a classical π-conjugated molecule, 4,4'-(1,4-phenylenedi-2,1-ethenediyl) bis-pyridine (DPB), was designed and synthesized as a substituent. Because of this modification, P5DPB exhibits several unique properties that differ from those of common pillar[5]arenes. The P5DPB neutral pyridine shows good selectivity for Ag⁺ and Fe³⁺. The presence of Ag⁺ ions cause a blue shift (from yellow-green to green) and a decrease in the intensity of the P5DPB emission, while the addition of Fe³⁺ significantly quenches the P5DPB fluorescence. In addition, P5DPB satisfies the conditions for the construction of an energy transfer system with the commonly used Rhodamine B dye and shows great potential for the development of artificial light-harvesting systems. This work provides a new approach for the construction of energy transfer systems and a new reference for metal detection based on derivatized pillar[n]arenes, greatly enriching the applications of these systems.
- Pillar[5]arene,
- Modification,
- Energy transfer system,
- Metal detection
1. [1]
  T. Ogoshi, S. Kanai, S. Fujinami, T. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 130 (2008) 5022–5023. doi: 10.1021/ja711260m
2. [2]
  T. Ogoshi, T. Aoki, K. Kitajima, et al., J. Org. Chem. 76 (2011) 328–331. doi: 10.1021/jo1020823
3. [3]
  Y. Cai, Z. Zhang, Y. Ding, et al., Chin. Chem. Lett. 32 (2021) 1267–1279. doi: 10.1016/j.cclet.2020.10.036
4. [4]
  Y. Ma, X. Chi, X. Yan, et al., Org. Lett. 14 (2012) 1532–1535. doi: 10.1021/ol300263z
5. [5]
  T. Ogoshi. J.I. Phenom, Macrocyclic Chem. 72 (2012) 247–262. doi: 10.1007/s10847-011-0027-2
6. [6]
  N.L. Strutt, R.S. Forgan, J.M. Spruell, Y.Y. Botros, J. Stoddart, J. Am. Chem. Soc. 133 (2011) 5668–5671. doi: 10.1021/ja111418j
7. [7]
  K. Kitajima, T. Ogoshi, T. Yamagishi, Chem. Commun. 50 (2014) 2925–2927. doi: 10.1039/C3CC49794A
8. [8]
  L. Escobar, P. Ballester, Chem. Rev. 121 (2021) 2445–2514. doi: 10.1021/acs.chemrev.0c00522
9. [9]
  B.L. Ho, D. Tian, J. Liu, et al., Inorg. Chem. 55 (2016) 10580–10586. doi: 10.1021/acs.inorgchem.6b01809
10. [10]
  H. Behera, L. Yang, J.L. Hou, Chin. J. Chem. 38 (2020) 215–217. doi: 10.1002/cjoc.201900408
11. [11]
  X. Yuan, Y. Cai, L. Chen, et al., Separ. Purif. Technol. 230 (2020) 115843. doi: 10.1016/j.seppur.2019.115843
12. [12]
  T. Kakuta, T. Yamagishi, T. Ogoshi, Acc. Chem. Res. 51 (2018) 1656–1666. doi: 10.1021/acs.accounts.8b00157
13. [13]
  Y. Cai, X. Yan, S. Wang, et al., Inorg. Chem. 60 (2021) 2883–2887. doi: 10.1021/acs.inorgchem.0c03645
14. [14]
  C. Peng, W. Liang, J. Ji, et al., Chin. Chem. Lett. 32 (2021) 345–348. doi: 10.1016/j.cclet.2020.03.079
15. [15]
  N.L. Strutt, H. Zhang, S.T. Schneebeli, J.F. Stoddart, Acc. Chem. Res. 47 (2014) 2631–2642. doi: 10.1021/ar500177d
16. [16]
  X. Xu, V.V. Jerca, R. Hoogenboom, Angew. Chem. Int. Ed. 59 (2020) 6314–6316. doi: 10.1002/anie.202002467
17. [17]
  D. Strilets, S. Fa, A. Hardiagon, et al., Angew. Chem. Int. Ed. 132 (2020) 23413–23419. doi: 10.1002/ange.202009219
18. [18]
  M. Cheng, G. Li, W. Xu, et al., Dyes Pigment. 194 (2021) 109646. doi: 10.1016/j.dyepig.2021.109646
19. [19]
  Y. Cai, S.A. Ansari, K. Fu, et al., J. Hazard. Mater. 405 (2021) 124214. doi: 10.1016/j.jhazmat.2020.124214
20. [20]
  B. Liu, X. Lu, X. Liao, et al., Appl. Surface Sci. 566 (2021) 150739. doi: 10.1016/j.apsusc.2021.150739
21. [21]
  J. Sun, Y. Dai, Y. Hou, et al., J. Phy. Chem. A 125 (2021) 2344–2355. doi: 10.1021/acs.jpca.1c01088
22. [22]
  S. Yu, Y. Wang, S. Chatterjee, et al., Chin. Chem. Lett. 32 (2021) 179–183. doi: 10.1016/j.cclet.2020.11.055
23. [23]
  L. Chen, Y. Wang, Y. Wan, et al., Chem, Eng, J. 387 (2020) 124087. doi: 10.1016/j.cej.2020.124087
24. [24]
  H. Zhang, J. Han, C. Li, Polym. Chem. 12 (2021) 2808–2824. doi: 10.1039/d1py00238d
25. [25]
  K. Zhong, S. Lu, W. Guo, et al., J. Mater. Chem. A 9 (2021) 10180–10185. doi: 10.1039/d1ta00483b
26. [26]
  G.T. Williams, C.J.E. Haynes, M. Fares, et al., Chem. Soc. Rev. 50 (2021) 2737–2763. doi: 10.1039/d0cs00948b
27. [27]
  X.Q. Ma, Y. Wang, T.B. Wei, et al., Dyes Pigment. 164 (2019) 279–286. doi: 10.1016/j.dyepig.2019.01.049
28. [28]
  C. Gouda, D. Barik, C. Maitra, et al., J. Mater. Chem. C 9 (2021) 2321–2333. doi: 10.1039/d0tc05000h
29. [29]
  X.L. Ni, S. Chen, Y. Yang, Z. Tao, J. Am. Chem. Soc. 138 (2016) 6177–6183. doi: 10.1021/jacs.6b01223
30. [30]
  J.F. Chen, G. Meng, Q. Zhu, S. Zhang, P. Chen, J. Mater. Chem. C 7 (2019) 11747–11751. doi: 10.1039/c9tc03831k
31. [31]
  X. Zhu, J. Zhao, F. Dai, et al., Spectrochimica Acta Part A: Mol. Biomol. Spectrosco. 250 (2021) 119381. doi: 10.1016/j.saa.2020.119381
32. [32]
  R. Hu, N.L.C. Leung, B.Z. Tang, Chem. Soc. Rev. 43 (2014) 4494–4562. doi: 10.1039/C4CS00044G
33. [33]
  Y. Hong, J.W.Y. Lama, B.Z. Tang, Chem. Soc. Rev. 40 (2011) 5361–5388. doi: 10.1039/c1cs15113d
34. [34]
  Y. Yang, X.L. Ni, T. Sun, H. Cong, G. Wei, RSC Adv. 4 (2014) 47000–47004. doi: 10.1039/C4RA07448C
35. [35]
  G. Zhou, X. Zhang, X.L. Ni, J. Hazard. Mate. 384 (2020) 121474. doi: 10.1016/j.jhazmat.2019.121474
36. [36]
  G. Heo, R. Manivannan, H. Kim, et al., Sensors & Actuators B: Chem. 297 (2019) 126723.
37. [37]
  M. Zhu, M. Yuan, X. Liu, et al., Org. Lett. 10 (2008) 1481–1484. doi: 10.1021/ol800197t
38. [38]
  R.M. Wen, S.D. Han, G.J. Ren, et al., Dalton Trans. 44 (2015) 10914–10917. doi: 10.1039/C4DT02445A
39. [39]
  X.L. Lia, Y. Wang, M.H. Zhang, et al., Dyes Pigment. 197 (2022) 109895. doi: 10.1016/j.dyepig.2021.109895
40. [40]
  X.M. Chen, Q. Cao, H.K. Bisoyi, et al., Angew. Chem. Int. Ed. 59 (2020) 10493–10497. doi: 10.1002/anie.202003427
41. [41]
  G. Sun, M. Zuo, W. Qian, et al., Green Synth. Catal. 2 (2021) 32–37. doi: 10.1016/j.gresc.2021.01.003
42. [42]
  M. Rao, W. Wu, C. Yang, Green Synth. Catal. 2 (2021) 131–144. doi: 10.1016/j.gresc.2021.03.005
43. [43]
  B.L. Ho, D. Tian, J. Liu, et al., Inorg. Chem. 55 (2016) 10580–10586. doi: 10.1021/acs.inorgchem.6b01809
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

A multiple-function fluorescent pillar[5]arene: Fe3+/Ag+ detection and light-harvesting system

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通讯作者: 陈斌, bchen63@163.com

A multiple-function fluorescent pillar[5]arene: Fe³⁺/Ag⁺ detection and light-harvesting system