Tunable Supramolecular Ag+-Host Interactions in Pillar[n]arene[m]quinones and Ensuing Specific Binding to 1-Alkynes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Different Pillararene Hosts
2.2. Determining Association Constants of Four Hosts with CF3COOAg via NMR Titration Experiments
2.3. Complexation of the Host Molecule with Silver Trifluoroacetate by ESI-MS
2.4. DFT-Optimized Structures for Six Different Pillararene-Ag2 Complexes
2.5. Specific Binding of 1-Alkynes to Silver-Loaded Pillararenes
3. Materials and Methods
3.1. Materials
General Procedures
3.2. Stoichiometry Determination
3.3. Binding Constants Determination
3.4. ESI-MS Competition Experiments
3.5. Optimized Geometry Structures of Pillararenes-Ag+ and Silver-Loaded-1-Alkyne Complexes
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Main Product | Solvent | Equiv. Oxidant | Reaction Time | Isolated Yield |
---|---|---|---|---|
P6Q1 | DCM/THF (9:1) | 2.2 | 30 min | 50% |
P6Q2 | DCM/THF (8:2) | 4.4 | 3 h | 45% |
P6Q3 | DCM/THF (7:3) | 6.6 | 3 h | 30% |
Host | Association Constant/M−1 |
---|---|
MeP5 | (1.41 ± 0.04) × 103 |
EtP5 | (2.24 ± 0.25) × 103 |
EtP6 | (2.04 ± 0.41) × 103 |
P6Q1 | (0.66 ± 0.08) × 103 |
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Zhu, Y.; Escorihuela, J.; Wang, H.; Sue, A.C.-H.; Zuilhof, H. Tunable Supramolecular Ag+-Host Interactions in Pillar[n]arene[m]quinones and Ensuing Specific Binding to 1-Alkynes. Molecules 2023, 28, 7009. https://doi.org/10.3390/molecules28207009
Zhu Y, Escorihuela J, Wang H, Sue AC-H, Zuilhof H. Tunable Supramolecular Ag+-Host Interactions in Pillar[n]arene[m]quinones and Ensuing Specific Binding to 1-Alkynes. Molecules. 2023; 28(20):7009. https://doi.org/10.3390/molecules28207009
Chicago/Turabian StyleZhu, Yumei, Jorge Escorihuela, Haiying Wang, Andrew C.-H. Sue, and Han Zuilhof. 2023. "Tunable Supramolecular Ag+-Host Interactions in Pillar[n]arene[m]quinones and Ensuing Specific Binding to 1-Alkynes" Molecules 28, no. 20: 7009. https://doi.org/10.3390/molecules28207009