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Abstract

Hemicucurbituril-Porphyrin Supramolecular Systems for Pollutant Sensing and Remediation †

Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia Tee 15, 12618 Tallinn, Estonia
*
Author to whom correspondence should be addressed.
Presented at the International Conference EcoBalt 2023 “Chemicals & Environment”, Tallinn, Estonia, 9–11 October 2023.
Proceedings 2023, 92(1), 87; https://doi.org/10.3390/proceedings2023092087
Published: 30 January 2024
(This article belongs to the Proceedings of International Conference EcoBalt 2023 "Chemicals & Environment")
Hemicucurbiturils are members of the single-bridged cucurbituril family, formed through templated synthesis in a single step. This class of compounds is known for its ability to form inclusion complexes with electron-rich species. We have developed sustainable synthesis methods for chiral hemicucurbit[n]urils (where n = 6 or 8) and their derivatives [1,2,3,4]. Additionally, we have demonstrated that cyclohexanohemicucurbiturils can form external complexes with metalloporphyrins [5]. Porphyrins are well known for their optical and photochemical properties, which are extensively utilized in sensing and catalysis applications. Chirality sensing adds another viewpoint to sensing systems, and we have shown that toxic organocatalysts can be sensed via complex formation with Zn porphyrins [6]. By merging chiral hemicucurbiturils and metalloporphyrins via non-covalent interactions into a solid thin material, one can construct an enantioselective electronic nose and very selectively discriminate different analytes and their handedness [7]. In this conference, we will present our findings on how hemicucurbiturils and porphyrins, as supramolecular receptors, can be employed for optical and gravimetric sensing, as well as for the remediation of chemical pollutants.

Author Contributions

Conceptualization, R.A.; methodology, R.A., V.B. and D.K.; investigation, N.K., T.J., M.-L.B. and M.Š.; All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the Estonian Research Council, grant number PRG399, and the European Union’s H2020- FETOPEN, grant 828779 (INITIO).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflicts of interest.

References

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  2. Prigorchenko, E.; Öeren, M.; Kaabel, S.; Fomitšenko, M.; Reile, I.; Järving, I.; Tamm, T.; Topic, F.; Rissanen, K.; Aav, R. Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril. Chem. Commun. 2015, 51, 10921. [Google Scholar] [CrossRef] [PubMed]
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  4. Dalidovich, T.; Mishra, K.A.; Shalima, T.; Kudrjašova, M.; Kananovich, D.G.; Aav, R. Mechanochemical Synthesis of Amides with Uronium-Based Coupling Reagents: A Method for Hexa-amidation of Biotin[6]uril. ACS Sustain. Chem. Eng. 2020, 8, 15703. [Google Scholar] [CrossRef]
  5. Ustrnul, L.; Kaabel, S.; Burankova, T.; Martõnova, J.; Adamson, J.; Konrad, N.; Burk, P.; Borovkov, V.; Aav, R. Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8). Chem. Commun. 2019, 55, 14434. [Google Scholar] [CrossRef] [PubMed]
  6. Konrad, N.; Horetski, M.; Sihtmäe, M.; Truong, K.N.; Osadchuk, I.; Burankova, T.; Kielmann, M.; Adamson, J.; Kahru, A.; Rissanen, K.; et al. Thiourea Organocatalysts as Emerging Chiral Pollutants: En Route to Porphyrin-Based (Chir)Optical Sensing. Chemosensors 2021, 9, 278. [Google Scholar] [CrossRef]
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Share and Cite

MDPI and ACS Style

Aav, R.; Borovkov, V.; Kananovich, D.; Konrad, N.; Jarg, T.; Brük, M.-L.; Šakarašvili, M. Hemicucurbituril-Porphyrin Supramolecular Systems for Pollutant Sensing and Remediation. Proceedings 2023, 92, 87. https://doi.org/10.3390/proceedings2023092087

AMA Style

Aav R, Borovkov V, Kananovich D, Konrad N, Jarg T, Brük M-L, Šakarašvili M. Hemicucurbituril-Porphyrin Supramolecular Systems for Pollutant Sensing and Remediation. Proceedings. 2023; 92(1):87. https://doi.org/10.3390/proceedings2023092087

Chicago/Turabian Style

Aav, Riina, Victor Borovkov, Dzmitry Kananovich, Nele Konrad, Tatsiana Jarg, Mari-Liis Brük, and Marko Šakarašvili. 2023. "Hemicucurbituril-Porphyrin Supramolecular Systems for Pollutant Sensing and Remediation" Proceedings 92, no. 1: 87. https://doi.org/10.3390/proceedings2023092087

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