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Self-Assembled Two-Dimensional Organic Layers in Solution Phase Based on Cucurbit[8]uril-Mediated Host-Guest Interactions

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Handbook of Macrocyclic Supramolecular Assembly

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Abstract

The construction of two-dimensional (2D) materials has drawn considerable attention in recent years due to their unique properties originating from the graphene-like 2D nature. In comparison with inorganic 2D matters, 2D organic layers exhibit abundant structural diversity and building strategies. This chapter summarizes the recent advance of 2D organic monolayers with periodic supramolecular framework structures. These ultrathin self-assembled architectures, termed as 2D supramolecular organic frameworks (SOFs), are homogeneously constructed in solution phase through self-assembly driven by cucurbit[8]uril (CB[8])-mediated host-guest interactions. They are soluble while maintaining stable network structures in solutions, which exhibit unique structural features and interesting properties.

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References

  1. Zhuang X, Mai Y, Wu D, Zhang F, Feng X (2015) Two-Dimensional soft nanomaterials: A fascinating world of materials. Adv Mater 27:403–427

    Article  CAS  Google Scholar 

  2. Servalli M, Schlüter AD (2017) Synthetic Two-Dimensional polymers. Annu Rev Mater Res 47:361–389

    Article  CAS  Google Scholar 

  3. Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV, Grigorieva IV, Firsov AA (2004) A. Electric field effect in atomically thin carbon films. Science 306:666–669

    Article  CAS  Google Scholar 

  4. Amo-Ochoa P, Welte L, Gonzälez-Prieto R, Miguel PJS, Gómez-Garcia CJ, Mateo-Marti E, Delgado S, Gómez-Herrero J, Zamora F (2010) Single layers of a multifunctional laminar Cu(I,II) coordination polymer. Chem Commun 46:3262–3264

    Article  CAS  Google Scholar 

  5. Bunck DN, Dichtel WR (2013) Bulk synthesis of exfoliated two-dimensional polymers using hydrazone-linked covalent organic frameworks. J Am Chem Soc 135:14952–14955

    Article  CAS  Google Scholar 

  6. Lafferentz L, Eberhardt V, Dri C, Africh C, Comelli G, Esch F, Hecht S, Grill L (2012) Controlling on-surface polymerization by hierarchical and substrate-directed growth. Nat Chem 4:215–220

    Article  CAS  Google Scholar 

  7. Dai W, Shao F, Szczerbiński J, McCaffrey R, Zenobi R, Jin Y, Schluter AD, Zhang W (2016) Synthesis of a Two-Dimensional covalent organic monolayer through dynamic imine chemistry at the Air/Water interface. Angew Chem Int Ed 55:213–217

    Article  CAS  Google Scholar 

  8. Zhou D, Tan X, Wu H, Tian L, Li M (2019) Synthesis of C–C bonded Two-Dimensional conjugated covalent organic framework films by suzuki polymerization on a Liquid–Liquid interface. Angew Chem Int Ed 58:1376–1381

    Article  CAS  Google Scholar 

  9. Palermo V, Samorì P (2007) Molecular self-assembly across multiple length scales. Angew Chem Int Ed 46:4428–4432

    Article  CAS  Google Scholar 

  10. Guo S, Liu X, Yao C, Lu C, Chen Q, Hu XY, Wang L (2016) Photolysis of a bola-type supra-amphiphile promoted by water-soluble pillar[5] arene-induced assembly. Chem Commun 52:10751–10754

    Article  CAS  Google Scholar 

  11. Liu Y, Yu Y, Gao J, Wang Z, Zhang X (2010) Water-soluble supramolecular polymerization driven by multiple host-stabilized charge-transfer interactions. Angew Chem Int Ed 49:6576–6579

    Article  CAS  Google Scholar 

  12. Tian J, Zhou TY, Zhang SC, Aloni S, Altoe MV, Xie SH, Wang H, Zhang DW, Zhao X, Liu Y, Li ZT (2014) Three-dimensional periodic supramolecular organic framework ion sponge in water and microcrystals. Nat Commun 5:5574

    Article  CAS  Google Scholar 

  13. Tian J, Chen L, Zhang DW, Liu Y, Li ZT (2016) Supramolecular organic frameworks: engineering periodicity in water through host-guest chemistry. Chem Commun 52:6351–6362

    Article  CAS  Google Scholar 

  14. Zhang KD, Tian J, Hanifi D, Zhang Y, Sue ACH, Zhou TY, Zhang L, Zhao X, Liu Y, Li ZT (2013) Toward a single-layer two-dimensional honeycomb supramolecular organic framework in water. J Am Chem Soc 135:17913–17918

    Article  CAS  Google Scholar 

  15. Zhang ZJ, Zhang HY, Chen L, Liu Y (2011) Interconversion between [5] pseudorotaxane and [3] pseudorotaxane by pasting/detaching two axle molecules. J Org Chem 76:8270–8276

    Article  CAS  Google Scholar 

  16. Kosower EM, Cotter JL (1964) Stable free radicals. II. The reduction of 1-methyl-4-cyanopyridinium ion to methylviologen cation radical. J Am Chem Soc 86:5524–5527

    Article  CAS  Google Scholar 

  17. Jeon WS, Kim HJ, Lee C, Kim K (2002) Control of the stoichiometry in host-guest complexation by redox chemistry of guests: Inclusion of methylviologen in cucurbit[8]uril. Chem Commun 1828–1829

    Google Scholar 

  18. Zhang L, Zhou T-Y, Tian J, Wang H, Zhang D-W, Zhao X, Liu Y, Li ZT (2014) A two-dimensional single-layer supramolecular organic framework that is driven by viologen radical cation dimerization and further promoted by cucurbit[8]uril. Polym Chem 5:4715–4721

    Article  CAS  Google Scholar 

  19. Zhang X, Nie C-B, Zhou T-Y, Qi Q-Y, Fu J, Wang X-Z, Dai L, Chen Y, Zhao X (2015) The construction of single-layer two-dimensional supramolecular organic frameworks in water through the self-assembly of rigid vertexes and flexible edges. Polym Chem 6:1923–1927

    Article  CAS  Google Scholar 

  20. Kim HJ, Heo J, Jeon WS, Lee E, Kim J, Sakamoto S, Yamaguchi K, Kim K (2001) Selective inclusion of a hetero-guest pair in a molecular host: Formation of stable charge-transfer complexes in cucurbit[8]uril. Angew Chem Int Ed 40:1526–1529

    Article  CAS  Google Scholar 

  21. Zhang L, Jia Y, Wang H, Zhang D-W, Zhang Q, Liu Y, Li ZT (2016) pH-Responsive single-layer honeycomb supramolecular organic frameworks that exhibit antimicrobial activity. Polym Chem 7:1861–1865

    Article  Google Scholar 

  22. Pfeffermann M, Dong R, Graf R, Zajaczkowski W, Gorelik T, Pisula W, Narita A, Müllen K, Feng X (2015) Free-Standing monolayer Two-Dimensional supramolecular organic framework with good internal order. J Am Chem Soc 137:14525–14532

    Article  CAS  Google Scholar 

  23. Zhou T-Y, Qi QY, Zhao QL, Fu J, Liu Y, Ma Z, Zhao X (2015) Highly thermally stable hydrogels derived from monolayered two-dimensional supramolecular polymers. Polym Chem 6:3018–3023

    Article  CAS  Google Scholar 

  24. Zhang Y, Zhou TY, Zhang KD, Dai JL, Zhu YY, Zhao X (2014) Encapsulation enhanced dimerization of a series of 4-Aryl-N-Methylpyridinium derivatives in water: New building blocks for Self-Assembly in aqueous media. Chem Asian J 9:1530–1534

    Article  CAS  Google Scholar 

  25. Zhang Y, Zhan TG, Zhou TY, Qi QY, Xu XN, Zhao X (2016) Fluorescence enhancement through the formation of a single-layer two-dimensional supramolecular organic framework and its application in highly selective recognition of picric acid. Chem Commun 52:7588–7591

    Article  CAS  Google Scholar 

  26. Zhang S, Yan JM, Qin AJ, Sun JZ, Tang BZ (2013) The specific detection of Cu(II) using an AIE-active alanine ester. Chin Chem Lett 24:668–672

    Article  CAS  Google Scholar 

  27. Xu SQ, Zhang X, Nie CB, Pang ZF, Xu XN, Zhao X (2015) The construction of a two-dimensional supramolecular organic framework with parallelogram pores and stepwise fluorescence enhancement. Chem Commun 51:16417–16420

    Article  CAS  Google Scholar 

  28. Chen XM, Zhang YM, Liu Y (2016) Adsorption of anionic dyes from water by thermostable supramolecular hydrogel. Supramol Chem 28:817–824

    Article  CAS  Google Scholar 

  29. Li Y, Dong Y, Miao X, Ren Y, Zhang B, Wang P, Yu Y, Li B, Isaacs L, Cao L (2018) Shape-Controllable and fluorescent supramolecular organic frameworks through aqueous Host-Guest complexation. Angew Chem Int Ed 57:729–733

    Article  CAS  Google Scholar 

  30. Lee HJ, Kim HJ, Lee EC, Kim J, Park SY (2018) Highly Luminescent and Water-Soluble Two-Dimensional supramolecular organic framework: All-Organic photosensitizer template for Visible-Light-Driven hydrogen evolution from water. Chem Asian J 13:390–394

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

    Shu-Yan Jiang & Xin Zhao

Authors
  1. Shu-Yan Jiang
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  2. Xin Zhao
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Corresponding author

Correspondence to Xin Zhao .

Editor information

Editors and Affiliations

  1. College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China

    Yu Liu

  2. College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China

    Yong Chen

  3. College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China

    Heng-Yi Zhang

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Jiang, SY., Zhao, X. (2020). Self-Assembled Two-Dimensional Organic Layers in Solution Phase Based on Cucurbit[8]uril-Mediated Host-Guest Interactions. In: Liu, Y., Chen, Y., Zhang, HY. (eds) Handbook of Macrocyclic Supramolecular Assembly . Springer, Singapore. https://doi.org/10.1007/978-981-15-2686-2_29

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