Citation: Xiaofei NIU, Ke WANG, Fengyan SONG, Shuyan YU. Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057 shu

Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-

School of Chemistry and Life Science, Beijing University of Technology, Beijing 100124, China

Corresponding author: Fengyan SONG, fengyansong@bjut.edu.cn Shuyan YU, selfassembly@bjut.edu.cn
Received Date: 2 February 2024
Revised Date: 28 May 2024

Figures(5)

In this study, parallelogram-like macrocyclic supramolecular metallacycles [Pd₆(bpy)₆(L¹)₄](PF₆)₈ (1a) and [Pd₆(bpy)₆(L²)₄](PF₆)₈ (2a), where HL¹=1-(1H-pyrazole-4-yl)-4-(4-pyridyl)benzene, HL²=9-(1H-pyrazole-4-yl)-10-(4-pyridyl)anthracene, and bpy=2, 2'-bipyridine, are synthesized by reacting aryl pyrazole pyridine ligands with dipalla-dium corners in aqueous solutions via metal-directed hierarchical self-assembly. The structures of the supramolecular Pd parallelograms are confirmed through single-crystal X-ray diffraction. Notably, the two parallelogram metallacycles can be used as"turn-on"fluorescence sensors to detect HSO₃^- through a disassembly mechanism. In addition, the 1a-based sensor shows selective detection of HSO₃^- without interference from other anions. The detection limit was as low as 0.131 μmol·L^-1. Furthermore, complex 1a presented the semiquantitative visual detection ability for HSO₃^- in the test trip mode via fluorescence changes.
- self-assembly,
- supramolecular Pd parallelogram,
- fluorescence detection,
- supramolecular crystal,
- bisulfite probe
1. [1]
  Sun Y Q, Liu J, Zhang J Y, Yang T, Guo W. Fluorescent probe for biological gas SO₂ derivatives bisulfite and sulfite[J]. Chem. Commun., 2013,49(26):2637-2639. doi: 10.1039/c3cc39161b
2. [2]
  ZHU G Y. Progress in monitoring technology for sulfur dioxide in the atmosphere[J]. Chin. J. Anal Chem., 1976(3):224-234.
3. [3]
  Wang K N, Zhu Y L, Xing M M, Cao D X, Guan R F, Zhao S F, Liu Z Q, Mao Z W. Two-photon fluorescence probes for mitochondria imaging and detection of sulfite/bisulfite in living cells[J]. Sens. Actuator BChem., 2019,295:215-222. doi: 10.1016/j.snb.2019.05.077
4. [4]
  Meng Z Q, Yang Z H, Li J L, Zhang Q X. The vasorelaxant effect and its mechanisms of sodium bisulfite as a sulfur dioxide donor[J]. Chemosphere, 2012,89(5):579-584. doi: 10.1016/j.chemosphere.2012.05.056
5. [5]
  Chan J, Dodani S C, Chang C J. Reaction-based small-molecule fluorescent probes for chemoselective bioimaging[J]. Nat. Chem., 2012,4:973-984. doi: 10.1038/nchem.1500
6. [6]
  Li J, Gao Y, Guo H R, Li X K, Tang H Y, Li J, Guo Y. A novel colorimetric and ratiometric fluorescent probe for selective detection of bisulfite in real samples and living cells[J]. Dyes Pigment, 2019,263:285-290.
7. [7]
  Deng C C, Xu Z Y, Sun Z, Xie J H, Luo H Q, Li N B. One-step synthesis of aldehyde-functionalized dual-emissive carbon dots for ratiometric fluorescence detection of bisulfite in food samples[J]. Food Chem, 2023,405134961. doi: 10.1016/j.foodchem.2022.134961
8. [8]
  Chao J B, Wang H J, Zhang Y B, Yin C X, Huo F J, Sun J Y, Zhao M G. A novel pyrene-based dual multifunctional fluorescent probe for differential sensing of pH and HSO₃^- and their bioimaging in live cells[J]. New. J. Chem, 2018,42(5):3322-3333. doi: 10.1039/C7NJ03903D
9. [9]
  Guo L E, Zhang J F, Liu X Y, Zhang L M, Zhang H L, Chen J H, Xie X G, Zhou Y, Luo K, Yoon J. Phosphate ion targeted colorimetric and fluorescent probe and its use to monitor endogeneous phosphate ion in a hemichannel-closed cell[J]. Anal. Chem., 2015,87:1196-1201. doi: 10.1021/ac503818p
10. [10]
  Zhang H Y, Huang Z J, Feng G Q. Colorimetric and ratiometric fluorescent detection of bisulfite by a new HBT-hemicyanine hybrid[J]. Anal. Chim. Acta, 2016,920:72-79. doi: 10.1016/j.aca.2016.03.027
11. [11]
  Wu W L, Ma H L, Huang M F, Miao J Y, Zhao B X. Mitochondriatargeted ratiometric fluorescent probe based on FRET for bisulfite[J]. Sens. Actuator B-Chem, 2017,241:239-244. doi: 10.1016/j.snb.2016.10.028
12. [12]
  Liu Y, Wu L Q, Dai Y X, Li Y P, Qi S L, Du J S, Yang Q B, Xu H, Li Y X. A novel fluorescent probe based on a triphenylamine derivative for the detection of HSO 3with high sensitivity and selectivity[J]. Anal. Methods, 2021,13(33):3667-3675. doi: 10.1039/D1AY00800E
13. [13]
  LI F, TANG Y H, GUO R, LIN W Y. Development of highly sensitive mitochondrial targeted nearinfrared sulfur dioxide fluorescent probes and imaging studies in cells and mice[J]. Chin. J. Org Chem, 2021,41(3):1108-1116.
14. [14]
  Shi Q, Shen L Y, Xu H, Wang Z Y, Yang X J, Huang Y L, Redshaw C, Zhang Q L. A 1-hydroxy-2, 4-diformylnaphthalene-based fluorescent probe and its detection of sulfites/bisulfite[J]. Molecules, 2021,263064. doi: 10.3390/molecules26113064
15. [15]
  Tamima U, Singha S, Kim H R, Reo Y J, Jun Y W, Das A, Ahn K H. A benzocoumarin based two-photon fluorescent probe for ratiometric detection of bisulfite[J]. Sens. Actuator B-Chem, 2018,277:576-583. doi: 10.1016/j.snb.2018.09.052
16. [16]
  Han Y Y, Huang Y, Lin Q W, Tang L Y, Yang G Y, Xin H T, Zhao S F, Guan R F, Wang K N, Cao D X. Bifunctional fluorescent probe for the recognition of hydrazine and bisulfite in lipid droplets[J]. Sens. Actuator B-Chem., 2023,393134181. doi: 10.1016/j.snb.2023.134181
17. [17]
  Wang H, Wu X M, Yang S X, Tian H Y, Liu Y G, Sun B G. A dualsite fluorescent probe for separate detection of hydrogen sulfide and bisulfite[J]. Dyes Pigment., 2019,160:757-764. doi: 10.1016/j.dyepig.2018.09.020
18. [18]
  Yang W C, Li S Y, Ni S N, Liu G Z. Advances in FRET-based biosensors from donor-acceptor design to applications[J]. Aggregate, 2023,5(2)e460.
19. [19]
  WANG C, YANG M, DENG X Y. A benzimidazole based fluorescence enhanced probe for detecting bisulfite and its practical application[J]. Chinese J. Inorg. Chem, 2020,36(4):762-768.
20. [20]
  Ma L, Haynes C J E, Grommet A B, Walczak A, Parkins C C, Doherty C M, Longley L, Tron A, Stefankiewicz A R, Bennett T D, Nitschke J R. Coordination cages as permanently porous ionic liquids[J]. Nat. Chem., 2020,12:270-275. doi: 10.1038/s41557-020-0419-2
21. [21]
  Li Y C, Li X Z, Li L L, Xiao B, Wu J G, Li H C, Li D Y, He C. Phenoxazine-based supramolecular tetrahedron as biomimetic lectin for glucosamine recognition[J]. Chin. Chem. Lett., 2021,32(2):735-739. doi: 10.1016/j.cclet.2020.07.028
22. [22]
  Woods C Z, Wu H T, Ngai C, Camara B D, Julian R R, Hooley R J. Modifying the internal substituents of self-assembled cages controls their molecular recognition and optical properties[J]. Dalton Trans., 2022,51:10920-10929. doi: 10.1039/D2DT01451C
23. [23]
  Begato F, Licini G, Zonta C. Programmed guest confinement via hierarchical cage to cage transformations[J]. Chem. Sci., 2023,14(30):8147-8151. doi: 10.1039/D3SC01368E
24. [24]
  Zhang D W, Ronson T K, Zou Y Q, Nitschke J R. Metal-organic cages for molecular separations[J]. Nat. Rev. Chem., 2021,5:168-182. doi: 10.1038/s41570-020-00246-1
25. [25]
  Hou Y J, Wu K, Wei Z W, Li K, Lu Y L, Zhu C Y, Wang J S, Pan M, Jiang J J, Li G Q, Su C Y. Design and enantioresolution of homochiral Fe(Ⅱ)-Pd(Ⅱ) coordination cages from stereolabile metalloligands: Stereochemical stability and enantioselective separation[J]. J. Am. Chem. Soc., 2018,140:18183-18191. doi: 10.1021/jacs.8b11152
26. [26]
  Kou Y L, Tong J, Meng C, Yuan Q, Wang J, Yu S Y. Reversible and turn-on fluorescence detection of phosphate in aqueous solution and living cell imaging by supramolecular metallacycles with AIE-active ligands[J]. ACS Appl. Mater. Interfaces, 2023,15:10828-40838.
27. [27]
  Wang P P, Tong J, Meng C, Yuan Q, Deng W, Yu S Y, Ma H W. Self-assembly of tripyrazolate-linked[M₆L₂] cages for the selective sensing of HSO₃^- and gaseous SO₂ by turn-on fluorescence[J]. Dalton Trans., 2023,52(19):6129-6137.
28. [28]
  Cui Y, Chen Z M, Jiang X F, Tong J, Yu S Y. Self-assembly and anion sensing of metal-organic[M₆L₂] cages from fluorescent triphe-nylamine tri-pyrazoles with dipalladium (Ⅱ, Ⅱ) corners[J]. Dalton Trans., 2017,46(18):5801-5805. doi: 10.1039/C7DT00179G
29. [29]
  Liu Y, Liu F Z, Yan K K. Mechanochemical access to a short-lived cyclic dimer Pd₂L₂: An elusive kinetic species en route to molecular triangle Pd₃L₃ and molecular square Pd₄L₄[J]. Angew. Chem. Int. Ed., 2022,61(18)e202116980. doi: 10.1002/anie.202116980
30. [30]
  Krishnaswamy S, Prusty S, Chartrand D, Hanan G S, Chand D K. Self-assembled molecular squares as supramolecular tectons[J]. Cryst. Growth Des., 2018,18:2016-2030. doi: 10.1021/acs.cgd.7b01425
31. [31]
  Behnia A, Boyle P D, Fard M A. Pincer-plus-one ligands in self-assembly with palladium(Ⅱ): A molecular square and a molecular tetrahedron[J]. Dalton Trans., 2016,45(48):19485-19490. doi: 10.1039/C6DT04264C
32. [32]
  Zhou M Y, Yu Z S, Deng W, Lu H L, Niu X F, Tong J, Yu S Y. [M₈L₄]⁸⁺-type squares self-assembled by dipalladium corners and bridging aromatic dipyrazole ligands for iodine capture[J]. Inorg Chem., 2023,62:10193-10202. doi: 10.1021/acs.inorgchem.3c00893
33. [33]
  Gupta G, You Y J, Hadiputra R, Jung J, Kang D K, Lee C Y. Heterome-tallic BODIPY-based molecular squares obtained by self-assembly: Synthesis and biological activities[J]. ACS Omega, 2019,4:13200-13208. doi: 10.1021/acsomega.9b01328
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Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-