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Linear Supramolecular Polymer Driven by Br⋅⋅⋅Br and Br⋅⋅⋅H Non-bonding Interactions Based on Inclusion-Complex of Octabromo-Functionalized Pillar[a]rene

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Abstract

Co-crystal structure of inclusion complex based on macrocyclic host of octabromo-functionalized pillar[5]arene (PilBr8) and guest 1-bromooctane (OctBr) molecule is discussed. The host-guest interactions are achieved by efficient C–H⋅⋅⋅O and C–H⋅⋅⋅π nonbonding interactions. The packing pattern of the crystal structure shows the inclusion-complex [PilBr8⊃OctBr] formed one-dimensional supramolecular polymer network driven by Br⋅⋅⋅H and Br⋅⋅⋅Br non-bonding interactions. Hirshfeld surface analysis revealed that the guest molecule plays an important role in formation of self-assembled linear supramolecular polymer trough head-to-tail halogen bond (Br⋅⋅⋅H).

Graphical Abstract

Co-crystal of inclusion complex based on bromo-functionlized pillar[5]arene with 1-bromooctane displays the assembly of linear supramolecular polymer promoted by halogen-bonding interactions.

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Data availability

The authors confirm that the data supporting the findings of this study are available within the article and its Supplementary material. Raw data that support the findings of this study are available from the corresponding author, upon reasonable request.

References

  1. Ji X, Ahmed M, Long L, Khashab NM, Huang F, Sessler JL (2019) Adhesive supramolecular polymeric materials constructed from macrocycle-based host–guest interactions. Chem Soc Rev 48:2682–2697

    Article  CAS  Google Scholar 

  2. Yang L, Tan X, Wang Z, Zhang X (2015) Supramolecular polymers: Historical development, preparation, characterization, and functions. Chem Rev 115:7196–7239

    Article  CAS  Google Scholar 

  3. Chapman R, Danial M, Koh ML, Jolliffe KA, Perrier S (2012) Design and properties of functional nanotubes from the self-assembly of cyclic peptide templates. Chem Soc Rev 41:6023–6041

    Article  CAS  Google Scholar 

  4. Krieg E, Bastings MMC, Besenius P, Rybtchinski B (2016) Supramolecular polymers in aqueous media. Chem Rev 116:2414–2477

    Article  CAS  Google Scholar 

  5. Liu Z, Qiao J, Niu Z, Wang Q (2012) Natural supramolecular building blocks: from virus coat proteins to viral nanoparticles. Chem Soc Rev 41:6178–6194

    Article  CAS  Google Scholar 

  6. Liu Y, Wang Z, Zhang X (2012) Characterization of supramolecular polymers. Chem Soc Rev 41:5922–5932

    Article  CAS  Google Scholar 

  7. Zheng B, Wang F, Dong S, Huang F (2012) Supramolecular polymers constructed by crown ether-based molecular recognition. Chem Soc Rev 41:1621–1636

    Article  CAS  Google Scholar 

  8. Ramamurthy V, Gupta S (2015) Supramolecular photochemistry: from molecular crystals to water-soluble capsules. Chem Soc Rev 44:119–135

    Article  CAS  Google Scholar 

  9. Chen Y, Huang F, Li ZT, Liu Y (2018) Controllable macrocyclic supramolecular assemblies in aqueous solution. Sci China Chem 61:979–992

    Article  CAS  Google Scholar 

  10. Assaf KI, Nau WM (2015) Cucurbiturils: from synthesis to high-affinity binding and catalysis. Chem Soc Rev 44:394–418

    Article  CAS  Google Scholar 

  11. Shetty D, Khedkar JK, Park KM, Kim K (2015) Can we beat the biotin–avidin pair? cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications. Chem Soc Rev 44:8747–8761

    Article  CAS  Google Scholar 

  12. Ogoshi T, Kanai S, Fujinami S, Yamagishi TA, Nakamoto Y (2008) para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host–guest property. J Am Chem Soc 130:5022–5023

    Article  CAS  Google Scholar 

  13. Al-Azemi TF, Vinodh M, Alipour FH, Mohamod AA (2017) Constitutional isomers of pentahydroxy-functionalized pillar[5]arenes: Synthesis, characterization, and crystal structures. J Org Chem 82:10945–10952

    Article  CAS  Google Scholar 

  14. Al-Azemi TF, Mohamod AA, Vinodh M, Alipour FH (2018) A new approach for the synthesis of mono- and A1/A2-dihydroxy-substituted pillar[5]arenes and their complexation with alkyl alcohols in solution and in the solid state. Org Chem Front 5:10–18

    Article  CAS  Google Scholar 

  15. Al-Azemi TF, Vinodh M, Mohamod AA, Alipour FH (2018) Single-crystal X-ray diffraction study of a host–guest system comprising monofunctionalized-hy­droxy pillar[5]arene and 1-octa­namine. Acta cryst E74:1117–1120

    Google Scholar 

  16. Al-Azemi TF, Vinodh M, Mohamod AA, Alipour FH (2018) Encapsulated dichloroethane-mediated interlocked supramolecular polymeric assembly of A1/A2-dihydroxy-octyloxy pillar[5]arene 1,2-dichloroethane monosolvate. Acta cryst E74:1471–1474

    Google Scholar 

  17. Li H, Yang Y, Xu F, Liang T, Wen H, Tian W (2019) Pillararene-based supramolecular polymers. Chem Commun 55:271–285

    Article  CAS  Google Scholar 

  18. Hu WB, Hu WJ, Zhao XL, Liu YA, Li JS, Jiang B, Wen K (2016) A1/A2-Diamino-substituted pillar[5]arene-based acid–base-responsive host–guest system. J Org Chem 81:3877–3881

    Article  CAS  Google Scholar 

  19. Ogoshi T, Masaki K, Shiga R, Kitajima K, Yamagishi TA (2011) Planar-chiral macrocyclic host pillar[5]arene: No rotation of units and isolation of enantiomers by introducing bulky substituents. Org Lett 13:1264–1266

    Article  CAS  Google Scholar 

  20. Aida T, Meijer EW, Stupp SI (2012) Functional supramolecular polymers. Science 335:813–817

    Article  CAS  Google Scholar 

  21. Gilday LC, Robinson SW, Barendt TA, Langton MJ, Mullaney BR, Beer PD (2015) Chem Rev 115(15):7118–7195

    Article  CAS  Google Scholar 

  22. Eichstaedt K, Wicher B, Gdaniec M, Połoński T (2016) Halogen bonded polypseudorotaxanes based on a pillar[5]arene host. CrystEngComm 18:5807–5810

    Article  CAS  Google Scholar 

  23. Liu PR, Li ZT, Shi BB, Liu JY, Zhu HTZ, Huang FH (2018) Formation of linear side-chain polypseudorotaxane with supramolecular polymer backbone through neutral halogen bonds and pillar[5]arene‐based host–guest interactions. Chem Eur J 24:4264–4267

    Article  CAS  Google Scholar 

  24. Al-Azemi TF, Vinodh M (2020) Pillar[5]arene-based self-assembled linear supramolecular polymer driven by guest halogen–halogen interactions in solid and solution states. Polym Chem 11:3305–3312

    Article  CAS  Google Scholar 

  25. Turner MJ, McKinnon JJ, Wolff SK, Grimwood DJ, Spackman PR, Jayatilaka D, Spackman AM (2017) CrystalExplorer17. University of Western Australia. Accessed from http://hirshfeldsurface.ne

  26. Al-Azemi TF, Vinodh M, Alipour FH, Mohamod AA (2019) Constitutional isomers of brominated-functionalized copillar[5]arenes: Synthesis, characterization, and crystal structures. RSC Adv 9:13814–13819

    Article  CAS  Google Scholar 

  27. Rigaku (2016) CrystalClear- SM Expert 2.1 b46. Rigaku Corporation, Tokyo

    Google Scholar 

  28. Rigaku (2017) CrystalStructure 4.2: crystal structure analysis package. Rigaku Corporation, Tokyo

    Google Scholar 

  29. Sheldrick GM (2015) Crystal structure refinement with SHELXL. Acta Cryst C71:3–8

    Google Scholar 

  30. Spek AL (2015) PLATON SQUEEZE: A tool for the calculation of the disordered solvent contribution to the calculated structure factors. Acta Cryst C 71:9–18

    Article  CAS  Google Scholar 

  31. Mukherjee A, Tothadi S, Desiraju GR (2014) Halogen bonds in crystal engineering: Like hydrogen bonds yet different. Acc Chem Res 47:2514–2524

    Article  CAS  Google Scholar 

  32. Spackman AM, Jayatilaka D (2009) Hirshfeld surface analysis. CrystEngComm 11:19–32

    Article  CAS  Google Scholar 

  33. McKinnon JJ, Spackman MA, Mitchell AS (2004) Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Cryst B 60:627–668

    Article  Google Scholar 

  34. McKinnon JJ, Jayatilaka D, Spackman MA (2007) Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces. Chem Commun 2007:3814–3816

    Article  Google Scholar 

Download references

Acknowledgements

The supports received from the Kuwait Foundation of Advancement of Science (KFAS), made available through research Grant No. PR17-14SC-07, and the facilities of RSPU (Grant Nos. GS03/08 and GS01/03) are gratefully acknowledged.

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  1. Chemistry Department, Kuwait University, P.O. Box 5969, 13060, Safat, Kuwait

    Mickey Vinodh & Talal F. Al-Azemi

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  1. Mickey Vinodh
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  2. Talal F. Al-Azemi
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Correspondence to Talal F. Al-Azemi.

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Vinodh, M., Al-Azemi, T.F. Linear Supramolecular Polymer Driven by Br⋅⋅⋅Br and Br⋅⋅⋅H Non-bonding Interactions Based on Inclusion-Complex of Octabromo-Functionalized Pillar[a]rene. J Chem Crystallogr 52, 399–406 (2022). https://doi.org/10.1007/s10870-022-00936-2

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