Solvent-Controlled Self-Assembled Oligopyrrolic Receptor
| Autor: | Steffen Bähring, Kejiang Liang, Hiroyuki Furuta, Fei Wang, Mads Christian Larsen, Masatoshi Ishida, Atanu Jana |
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| Rok vydání: | 2021 |
| Předmět: |
Supramolecular chemistry
supramolecular receptor Pharmaceutical Science macromolecular substances 010402 general chemistry 01 natural sciences Article Oligopyrrole Analytical Chemistry lcsh:QD241-441 lcsh:Organic chemistry colorimetric acid-sensing Drug Discovery Polymer chemistry host–guest chemistry Physical and Theoretical Chemistry Receptor Host–guest chemistry Aqueous solution 010405 organic chemistry Chemistry Organic Chemistry 0104 chemical sciences Solvent Chemistry (miscellaneous) Supramolecular receptor Anhydrous Proton NMR Molecular Medicine Titration oligopyrrole Colorimetric acid-sensing |
| Zdroj: | Wang, F, Larsen, M C, Bähring, S, Ishida, M, Furuta, H & Jana, A 2021, ' Solvent-Controlled Self-Assembled Oligopyrrolic Receptor ', Molecules, vol. 26, no. 6, 1771 . https://doi.org/10.3390/molecules26061771 Molecules, Vol 26, Iss 1771, p 1771 (2021) Molecules Volume 26 Issue 6 |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules26061771 |
| Popis: | We report a fully organic pyridine-tetrapyrrolic U-shaped acyclic receptor 10, which prefers a supramolecular pseudo-macrocyclic dimeric structure (10)2 in a less polar, non-coordinating solvent (e.g., CHCl3). Conversely, when it is crystalized from a polar, coordinating solvent (e.g., N,N-dimethylformamide, DMF), it exhibited an infinite supramolecular one-dimensional (1D) “zig-zag” polymeric chain, as inferred from the single-crystal X-ray structures. This supramolecular system acts as a potential receptor for strong acids, e.g., p-toluenesulfonic acid (PTSA), methane sulfonic acid (MSA), H2SO4, HNO3, and HCl, with a prominent colorimetric response from pale yellow to deep red. The receptor can easily be recovered from the organic solution of the host–guest complex by simple aqueous washing. It was observed that relatively stronger acids with pKa < −1.92 in water were able to interact with the receptor, as inferred from 1H NMR titration in tetrahydrofuran-d8 (THF-d8) and ultraviolet–visible (UV–vis) spectroscopic titrations in anhydrous THF at 298 K. Therefore, this new dynamic supramolecular receptor system may have potentiality in materials science research. |
| Databáze: | OpenAIRE |
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