Skip to main content
Log in

A pillar[5]arene-based supramolecular polymer network gel and its application in adsorption and removal of organic dye in water

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

A novel 3D supramolecular polymer network gel (DP5G) was successfully constructed by easy to synthesize tripodal guest (SZ) and thioacetylhydrazone functionalized di-pillar[5]arene host (DP5). Interestingly, the DP5G showed aggregation induced emission (AIE). Moreover, the DP5G displayed a 3D network structure, which was used to dye removal experiments. Notably, the xerogel DP5G could effectively remove cationic dyes (including crystal violet and rhodamine B) from aqueous solution and the removal percentages are 96.3% and 95.4%, respectively. In addition, the maximal adsorption capacity of DP5G towards crystal violet and rhodamine B are 19.65 mg/g and 22.85 mg/g, respectively. The stability of the 3D supramolecular polymer network gel (DP5G) was further investigated, which exhibited excellent stability toward outer stimuli such as pH, competitive agents, oxidant and reducing agent.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Lehn, J.M.: From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry. Chem. Soc. Rev. 36, 151–160 (2007)

    PubMed  CAS  Google Scholar 

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

    PubMed  CAS  Google Scholar 

  3. Zhou, Z., Yan, X., Cook, T.R., Saha, M.L., Stang, P.J.: Engineering functionalization in a supramolecular polymer: hierarchical self-organization of triply orthogonal non-covalent interactions on a supramolecular coordination complex platform. J. Am. Chem. Soc. 138, 806–809 (2016)

    PubMed  CAS  Google Scholar 

  4. Li, Z.Y., Zhang, Y., Zhang, C.W., Chen, L.J., Wang, C., Tan, H., Yu, Y., Li, X., Yang, H.B.: Cross-linked supramolecular polymer gels constructed from discrete multi-pillar[5]arene metallacycles and their multiple stimuli-responsive behavior. J. Am. Chem. Soc. 136, 8577–8589 (2014)

    PubMed  CAS  Google Scholar 

  5. Dong, S., Luo, Y., Yan, X., Zheng, B., Ding, X., Yu, Y., Ma, Z., Zhao, Q., Huang, F.: A dual-responsive supramolecular polymer gel formed by crown ether based molecular recognition. Angew. Chem. Int. Ed. 50, 1905–1909 (2011)

    CAS  Google Scholar 

  6. Xia, D., Wang, L., Lv, X., Chao, J., Wei, X., Wang, P.: Dual-responsive [2]pseudorotaxane on the basis of a pH-sensitive pillar[5]arene and its application in the fabrication of metallosupramolecular polypseudorotaxane. Macromolecules 51, 2716–2722 (2018)

    CAS  Google Scholar 

  7. Chen, H., Ma, X., Wu, S., Tian, H.: A rapidly self-healing supramolecular polymer hydrogel with photostimulated room-temperature phosphorescence responsiveness. Angew. Chem. Int. Ed. 53, 14149–14152 (2014)

    CAS  Google Scholar 

  8. Miyamae, K., Nakahata, M., Takashima, Y., Harada, A.: Self-healing, expansion-contraction, and shape-memory properties of a preorganized supramolecular hydrogel through host-guest interactions. Angew. Chem. Int. Ed. 54, 8984–8987 (2015)

    CAS  Google Scholar 

  9. Li, X., Li, Z., Yang, Y.W.: Tetraphenylethylene-interweaving conjugated macrocycle polymer materials as two-photon fluorescence sensors for metal ions and organic molecules. Adv. Mater. 30, 1800177 (2018)

    Google Scholar 

  10. Liu, Y., Lou, B., Shangguan, L., Cai, J., Zhu, H., Shi, B.: Pillar[5]arene-based organometallic cross-linked polymer: synthesis, structure characterization, and catalytic activity in the Suzuki–Miyaura coupling reaction. Macromolecules 51, 1351–1356 (2018)

    CAS  Google Scholar 

  11. Lin, Q., Fan, Y.Q., Mao, P.P., Liu, L., Liu, J., Zhang, Y.M., Yao, H., Wei, T.B.: Pillar [5] arene-based supramolecular organic framework with multi-guest detection and recyclable separation properties. Chem. Eur. J. 24, 777–783 (2018)

    PubMed  CAS  Google Scholar 

  12. Feng, W., Jin, M., Yang, K., Pei, Y., Pei, Z.: Supramolecular delivery systems based on pillararenes. Chem. Commun. 54, 13626–13640 (2018)

    CAS  Google Scholar 

  13. Zuo, M., Qian, W., Xu, Z., Shao, W., Hu, X., Zhang, D., Jiang, J., Sun, X., Wang, L.: Multiresponsive supramolecular theranostic nanoplatform based on pillar [5] arene and diphenylboronic acid derivatives for integrated glucose sensing and insulin delivery. Small. 14, 1801942 (2018)

    Google Scholar 

  14. Hu, C., Ma, N., Li, F., Fang, Y., Liu, Y., Zhao, L., Qiao, S., Li, X., Jiang, X., Li, T., Shen, F., Huang, Y., Luo, Q., Liu, J.: Cucurbit [8] uril-based giant supramolecular vesicles: highly stable, versatile carriers for photoresponsive and targeted drug delivery. ACS Appl. Mater. Interfaces 10, 4603–4613 (2018)

    PubMed  Google Scholar 

  15. Zhou, C., Lai, C., Huang, D., Zeng, G., Zhang, C., Cheng, M., Hu, L., Wan, J., Xiong, W., Wen, M., Wen, X., Qin, L.: Highly porous carbon nitride by supramolecular preassembly of monomers for photocatalytic removal of sulfamethazine under visible light driven. Appl. Catal. B 220, 202–210 (2018)

    CAS  Google Scholar 

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

    PubMed  CAS  Google Scholar 

  17. Liang, G.Y., Wu, G.Y., Wang, H.M., Su, J.X., Li, H., Lin, Q., Zhang, Y.M., Wei, T.B.: Unidirectional threading of tadpole-looking guests into a symmetric pillar [5] arene through host-guest complexation. J. Incl. Phenom. Macrocycl. Chem. 86(3–4), 173–181 (2016)

    CAS  Google Scholar 

  18. Fan, C., Wu, W., Chruma, J.J., Zhao, J., Yang, C.: Enhanced triplet-triplet energy transfer and upconversion fluorescence through host-guest complexation. J. Am. Chem. Soc. 138, 15405–15412 (2016)

    PubMed  CAS  Google Scholar 

  19. Yao, Y., Wei, X., Cai, Y., Kong, X., Chen, J., Wu, J., Shi, Y.: Hybrid supramolecular materials constructed from pillar [5] arene based host-guest interactions with photo and redox tunable properties. J. Colloid Interfaces Sci. 525, 48–53 (2018)

    CAS  Google Scholar 

  20. Yao, J., Wu, W., Liang, W., Feng, Y., Zhou, D., Chruma, J.J., Fukuhara, G., Mori, T., Inoue, Y., Yang, C.: Temperature-driven planar chirality switching of a pillar[5]arene-based molecular universal joint. Angew. Chem. Int. Ed. 56, 6869–6873 (2017)

    CAS  Google Scholar 

  21. Park, C., Kim, K.T.: Pillar [n] arenes and other cavitands: aspects of complex thermodynamics. Chin. J. Chem. 33, 311–318 (2015)

    CAS  Google Scholar 

  22. Ji, J., Li, Y., Xiao, C., Cheng, G., Luo, K., Gong, Q., Zhou, D., Chruma, J.J., Wu, W., Yang, C.: Supramolecular enantiomeric and structural differentiation of amino acid derivatives with achiral pillar[5]arene homologs. Chem. Commun. 56, 161–164 (2020)

    CAS  Google Scholar 

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

    PubMed  CAS  Google Scholar 

  24. Yang, K., Chao, S., Zhang, F., Pei, Y., Pei, Z.: Recent advances in the development of rotaxanes and pseudorotaxanes based on pillar [n] arenes: from construction to application. Chem. Commun. 55, 13198–13210 (2019)

    CAS  Google Scholar 

  25. Xiao, C., Wu, W., Liang, W., Zhou, D., Kanagaraj, K., Cheng, G., Su, D., Zhong, Z., Chruma, J.J., Yang, C.: Redox-triggered chirality switching and guest-capture/release with a pillar[6]arene-based molecular universal joint. Angew. Chem. Int. Ed. 59, 1–6 (2020)

    Google Scholar 

  26. Wang, P., Ma, J., Xia, D.: A H2S and I dual-responsive supramolecular polymer constructed via pillar [5] arene-based host-guest interactions and metal coordination. Org. Chem. Front. 5, 1297–1302 (2018)

    CAS  Google Scholar 

  27. Li, H., Chen, W., Xu, F., Fan, X., Liang, T., Qi, X., Tian, W.: A color-tunable fluorescent supramolecular hyperbranched polymer constructed by pillar [5] arene-based host-guest recognition and metal ion coordination interaction. Macromol. Rapid Commun. 39, 1800053 (2018)

    Google Scholar 

  28. Shi, B., Jie, K., Zhou, Y., Xia, D., Yao, Y.: Formation of fluorescent supramolecular polymeric assemblies via orthogonal pillar [5] arene-based molecular recognition and metal ion coordination. Chem. Commun. 51, 4503–4506 (2015)

    CAS  Google Scholar 

  29. Nazarova, A.A., Padnya, P.L., Gilyazeva, A.I., Khannanov, A.A., Evtugyn, V.G., Kutyreva, M.P., Klochkovb, V.V., Stoikov, I.I.: Supramolecular motifs for the self-assembly of monosubstituted pillar [5] arenes with an amide fragment: from nanoparticles to supramolecular polymers. New. J. Chem. 42, 19853–19863 (2018)

    CAS  Google Scholar 

  30. Zhu, Y., Xu, L., Wang, L., Tang, H., Cao, D.: Effect of scaffold structures on the artificial light-harvesting systems: a case study with an AIEE-active pillar[5]arene dyad. Chem. Commun. 55, 5910–5913 (2019)

    CAS  Google Scholar 

  31. Xia, W., Ni, M., Yao, C., Wang, X., Chen, D., Lin, C., Hu, X.Y., Wang, L.: Responsive gel-like supramolecular network based on pillar[6]arene-ferrocenium recognition motifs in polymeric matrix. Macromolecules 48, 4403–4409 (2015)

    CAS  Google Scholar 

  32. Xu, L., Wang, Z., Wang, R., Wang, L., He, X., Jiang, H., Tang, H., Cao, D., Tang, B.Z.: A Conjugated Polymeric Supramolecular Network with Aggregation-Induced Emission Enhancement: An Efficient Light-Harvesting System with an Ultrahigh Antenna Effect. Angew. Chem. Int. Ed. 58, 1–6 (2019)

    Google Scholar 

  33. Yang, J., Li, Z., Zhou, Y., Yu, G.: Construction of a pillar[5]arene-based linear supramolecular polymer and a photo-responsive supramolecular network. Polym. Chem. 5, 6645–6650 (2014)

    CAS  Google Scholar 

  34. Crini, G., Lichtfouse, E.: Advantages and disadvantages of techniques used for wastewater treatment. Environ. Chem. Lett. 17, 145–155 (2018)

    Google Scholar 

  35. Meerbergen, K., Crauwels, S., Willems, K.A., Dewil, R., Impe, J.V., Appels, L., Lievens, B.: Decolorization of reactive azo dyes using a sequential chemical and activated sludge treatment. J. Biosci. Bioeng. 124, 668–673 (2017)

    PubMed  CAS  Google Scholar 

  36. Mojiri, A., Ziyang, L., Hui, W., Ahmad, Z., Tajuddin, R.M., Abu Amr, S.S., Kindaichi, T., Aziz, H.A., Farraji, H.: Concentrated landfill leachate treatment with a combined system including electro-ozonation and composite adsorbent augmented sequencing batch reactor process. Process. Saf. Environ. 111, 253–262 (2017)

    CAS  Google Scholar 

  37. Ramar, V., Moothattu, S., Balasubramanian, K.: Metal free, sunlight and white light based photocatalysis using carbon quantum dots from Citrus grandis: A green way to remove pollution. Sol. Energy. 169, 120–127 (2018)

    CAS  Google Scholar 

  38. Djilali, Y., Elandaloussi, E.H., Aziz, A., de Ménorval, L.C.: Alkaline treatment of timber sawdust: A straightforward route toward effective low-cost adsorbent for the enhanced removal of basic dyes from aqueous solutions. J. Saudi. Chem. Soc. 20, S241–S249 (2016)

    CAS  Google Scholar 

  39. Bardajee, G.R., Hosseini, S.S., Vancaeyzeele, C.: Graphene oxide nanocomposite hydrogel based on poly (acrylic acid) grafted onto salep: an adsorbent for the removal of noxious dyes from water. New. J. Chem. 43, 3572–3582 (2019)

    Google Scholar 

  40. Ding, J.D., Chen, J.F., Lin, Q., Yao, H., Zhang, Y.M., Wei, T.B.: A multi-stimuli responsive metallosupramolecular polypseudorotaxane gel constructed by self-assembly of a pillar[5]arene-based pseudo[3] rotaxane via zinc ion coordination and its application for highly sensitive fluorescence recognition of metal ions. Polym. Chem. 9, 5370–5376 (2018)

    CAS  Google Scholar 

  41. Lin, Q., Zhong, K.P., Zhu, J.H., Ding, L., Su, J.X., Yao, H., Wei, T.B., Zhang, Y.M.: Iodine controlled pillar [5] arene-based multiresponsive supramolecular polymer for fluorescence detection of cyanide, mercury, and cysteine. Macromolecules 50, 7863–7871 (2017)

    CAS  Google Scholar 

  42. Guan, X.W., Lin, Q., Zhang, Y.M., Wei, T.B., Wang, J., Fan, Y.Q., Yao, H.: Pillar [5] arene-based spongy supramolecular polymer gel and its properties in multi-responsiveness, dye sorption, ultrasensitive detection and separation of Fe 3+. Soft Matter 15, 3241–3247 (2019)

    PubMed  CAS  Google Scholar 

  43. Luo, X.Z., Jia, X.J., Deng, J.H., Zhong, J.L., Liu, H.J., Wang, K.J., Zhong, D.C.: A microporous hydrogen-bonded organic framework: exceptional stability and highly selective adsorption of gas and liquid. J. Am. Chem. Soc. 135, 11684–11687 (2013)

    PubMed  CAS  Google Scholar 

  44. Cheng, N., Hu, Q., Guo, Y., Wang, Y., Yu, L.: Efficient and selective removal of dyes using imidazolium-based supramolecular gels. ACS Appl. Mater. Interfaces. 7, 10258–10265 (2015)

    PubMed  CAS  Google Scholar 

  45. Ji, X., Wu, R.T., Long, L., Guo, C., Khashab, N.M., Huang, F., Sessler, J.L.: Physical removal of anions from aqueous media by means of a macrocycle-containing polymeric network. J. Am. Chem. Soc. 140, 2777–2780 (2018)

    PubMed  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NSFC) (Nos. 21574104; 21662031; 21661028), the Natural Science Foundation of Gansu Province (1506RJZA273) and the Program for Changjiang Scholars and Innovative Research Team in University of Ministry of Education of China (IRT15R56).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Wen-Juan Qu, Qi Lin or Tai-Bao Wei.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 3255 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

An, JN., Qu, WJ., Zhang, QP. et al. A pillar[5]arene-based supramolecular polymer network gel and its application in adsorption and removal of organic dye in water. J Incl Phenom Macrocycl Chem 97, 137–145 (2020). https://doi.org/10.1007/s10847-020-01000-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-020-01000-2

Keywords

Navigation