Abstract
A novel multi-hybrid hemicucurbituril with good solubility in organic solvent has been synthesized by combining derived glycoluril, ethyleneurea, and aromatic group in one macrocycle. This macrocycle has exhibited properties in photoresponse and derivatization, and showed obvious interaction with Fe3+ and Cu2+ by the fluorescence spectra study. The modified hemicucurbituril could be easily converted to another imidazolidine-2,4-dione-containing macrocycle.
Similar content being viewed by others
References
Behrend, R., Meyer, E., Rusche, F.: I. ueber condensationsproducte aus glycoluril und formaldehyd. Justus Liebigs Ann. Chem. 339(1), 1–37 (1905). https://doi.org/10.1002/jlac.19053390102
Freeman, W.A., Mock, W.L., Shih, N.Y.: Cucurbituril. J. Am. Chem. Soc. 103(24), 7367–7368 (1981). https://doi.org/10.1021/ja00414a070
Kim, J., Jung, I.-S., Kim, S.-Y., Lee, E., Kang, J.-K., Sakamoto, S., Yamaguchi, K., Kim, K.: New cucurbituril homologues: syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 122(3), 540–541 (2000). https://doi.org/10.1021/ja993376p
Day, A., Arnold, A.P., Blanch, R.J., Snushall, B.: Controlling factors in the synthesis of cucurbituril and its homologues. J. Org. Chem. 66(24), 8094–8100 (2001). https://doi.org/10.1021/jo015897c
Blanch, R.J., Sleeman, A.J., White, T.J., Arnold, A.P., Day, A.I.: Cucurbit[7]uril and o-carborane self-assemble to form a molecular ball bearing. Nano Lett. 2(2), 147–149 (2002). https://doi.org/10.1021/nl015655s
Day, A.I., Blanch, R.J., Arnold, A.P., Lorenzo, S., Lewis, G.R., Dance, I.: A cucurbituril-based gyroscane: a new supramolecular form. Angew. Chem. Int. Ed. 41(2), 275–277 (2002). https://doi.org/10.1002/1521-3773(20020118)41:2%3c275::AID-ANIE275%3e3.0.CO;2-M
Li, Q., Qiu, S.-C., Zhang, J., Chen, K., Huang, Y., Xiao, X., Zhang, Y., Li, F., Zhang, Y.-Q., Xue, S.-F., Zhu, Q.-J., Tao, Z., Lindoy, L.F., Wei, G.: Twisted cucurbit[n]urils. Org. Lett. 18(16), 4020–4023 (2016). https://doi.org/10.1021/acs.orglett.6b01842
Isaacs, L., Park, S.-K., Liu, S., Ko, Y.H., Selvapalam, N., Kim, Y., Kim, H., Zavalij, P.Y., Kim, G.-H., Lee, H.-S., Kim, K.: The inverted cucurbit[n]uril family. J. Am. Chem. Soc. 127(51), 18000–18001 (2005). https://doi.org/10.1021/ja056988k
Mock, W.L., Shih, N.Y.: Host-guest binding capacity of cucurbituril. J. Org. Chem. 48(20), 3618–3619 (1983). https://doi.org/10.1021/jo00168a069
Mock, W.L., Shih, N.Y.: Structure and selectivity in host-guest complexes of cucurbituril. J. Org. Chem. 51(23), 4440–4446 (1986). https://doi.org/10.1021/jo00373a018
Mock, W.L., Shih, N.Y.: Organic ligand-receptor interactions between cucurbituril and alkylammonium ions. J. Am. Chem. Soc. 110(14), 4706–4710 (1988). https://doi.org/10.1021/ja00222a031
Mock, W.L., Shih, N.Y.: Dynamics of molecular recognition involving cucurbituril. J. Am. Chem. Soc. 111(7), 2697–2699 (1989). https://doi.org/10.1021/ja00189a053
Mock, W.L., Pierpont, J.: A cucurbituril-based molecular switch. Chem. Commun. (1990). https://doi.org/10.1039/c39900001509
Miyahara, Y., Goto, K., Oka, M., Inazu, T.: Remarkably facile ring-size control in macrocyclization: synthesis of hemicucurbit[6]uril and hemicucurbit[12]uril. Angew. Chem. Int. Ed. 43(38), 5019–5022 (2004). https://doi.org/10.1002/anie.200460764
Havel, V., Sadilova, T., Sindelar, V.: Unsubstituted bambusurils: post-macrocyclization modification of versatile intermediates. ACS Omega 3(4), 4657–4663 (2018). https://doi.org/10.1021/acsomega.8b00497
Svec, J., Necas, M., Sindelar, V.: Bambus[6]uril. Angew. Chem. Int. Ed. 49(13), 2378–2381 (2010). https://doi.org/10.1002/anie.201000420
Fiala, T., Ludvikova, L., Heger, D., Svec, J., Slanina, T., Vetrakova, L., Babiak, M., Necas, M., Kulhanek, P., Klan, P., Sindelar, V.: Bambusuril as a one-electron donor for photoinduced electron transfer to methyl viologen in mixed crystals. J. Am. Chem. Soc. 139(7), 2597–2603 (2017). https://doi.org/10.1021/jacs.6b08589
Lisbjerg, M., Jessen, B.M., Rasmussen, B., Nielsen, B.E., Madsen, A.Ø., Pittelkow, M.: Discovery of a cyclic 6 + 6 hexamer of d-biotin and formaldehyde. Chem. Sci. 5(7), 2647–2650 (2014). https://doi.org/10.1039/c4sc00990h
Andersen, N.N., Eriksen, K., Lisbjerg, M., Ottesen, M.E., Milhoj, B.O., Sauer, S.P.A., Pittelkow, M.: Entropy/enthalpy compensation in anion binding: biotin[6]uril and biotin-l-sulfoxide[6]uril reveal strong solvent dependency. J. Org. Chem. 84(5), 2577–2584 (2019). https://doi.org/10.1021/acs.joc.8b02797
Kaabel, S., Stein, R.S., Fomitsenko, M., Jarving, I., Friscic, T., Aav, R.: Size-control by anion templating in mechanochemical synthesis of hemicucurbiturils in the solid state. Angew. Chem. Int. Ed. 58(19), 6230–6234 (2019). https://doi.org/10.1002/anie.201813431
Li, Y., Li, L., Zhu, Y., Meng, X., Wu, A.: Solvent effect on pseudopolymorphism of hemicyclohexylcucurbit[6]uril. Cryst Growth Des. 9(10), 4255–4257 (2009). https://doi.org/10.1021/cg9007262
Kaabel, S., Adamson, J., Topic, F., Kiesila, A., Kalenius, E., Oeren, M., Reimund, M., Prigorchenko, E., Lookene, A., Reich, H.J., Rissanen, K., Aav, R.: Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution. Chem. Sci. 8(3), 2184–2190 (2017). https://doi.org/10.1039/c6sc05058a
Zeng, Q., Long, Q., Lu, J., Wang, L., You, Y., Yuan, X., Zhang, Q., Ge, Q., Cong, H., Liu, M.: Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions. Beilstein J. Org. Chem. 17, 2840–2847 (2021)
Parvari, G., Annamalai, S., Borovoi, I., Chechik, H., Botoshansy, M., Pappo, D., Keinan, E.: Multifarens: new modular cavitands. Chem. Commun. 50, 2494–2497 (2014). https://doi.org/10.1039/c3cc48284g
Svec, J., Dusek, M., Fejfarova, K., Stacko, P., Klan, P., Kaifer, A.E., Li, W., Hudeckova, E., Sindelar, V.: Anion-free bambus[6]uril and its supramolecular properties. Chem. Eur. J. 17(20), 5605–5612 (2011). https://doi.org/10.1002/chem.201003683
Anikina, L.V., Gazieva, G.A., Kravchenko, A.N.: Nootropic activity of N-(2-acetylaminoethyl)glycolurils. Russ. Chem. Bull. Int. Ed. 69(3), 563–566 (2020). https://doi.org/10.1007/s11172-020-2799-2
Lizal, T., Sindelar, V.: Bambusuril analogs based on alternating glycoluril and xylylene units. Beilstein J. Org. Chem. 15, 1268–1274 (2019). https://doi.org/10.3762/bjoc.15.124
Acknowledgements
The authors gratefully acknowledge the finance support of the National Natural Science Foundation of China [Nos. 21901053, 22261008]; “Chun Hui” Project of the Chinese Ministry of Education [Z2017007]; the Science and Technology Project of Guizhou Province [QKHJC [2017]1027]; and the talent introduction Program of Guizhou University [GDRJHZ2014-21].
Funding
National Natural Science Foundation of China, Nos. 21901053, 22261008, “Chun Hui” Project of the Chinese Ministry of Education, Z2017007, Science and Technology Project of Guizhou Province, QKHJC [2017]1027.
Author information
Authors and Affiliations
Contributions
XY, QZ, LW, YY, XC and ML wrote the main manuscript text and supplementary information; XY did most of the experiments, prepared Schemes 1-3 and Figure 1-4; QZ, QG, and HC helped the X-ray structure and the fluorescence spectra study. All authors reviewed the manuscript.
Corresponding author
Ethics declarations
Competing interests
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Yuan, X., Zeng, Q., Wang, L. et al. Synthesis of multi-hybrid hemicucurbiturils. J Incl Phenom Macrocycl Chem 103, 57–61 (2023). https://doi.org/10.1007/s10847-022-01176-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-022-01176-9