Solvent-Controlled Self-Assembled Oligopyrrolic Receptor †
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. X-ray Crystallography
2.3. Structural Behavior in Solution
2.4. Acid Recognition Studies Using Spectroscopy
2.5. Theoretical Studies
3. Materials and Methods
3.1. General Experiments
3.1.1. Chemicals and Consumables
- Iodine (I2) (CAS No: 7553-56-2), Triethylamine (Et3N) (CAS No: 121-44-8), Potassium carbonate (K2CO3) (CAS No: 584-08-7), Sodium bicarbonate (NaHCO3) (CAS No: 144-55-8), Sodium thiosulfate (Na2S2O3) (CAS No: 7772-98-7), Dichloromethane (CH2Cl2) (CAS No: 75-09-2) were purchased from Adamas-beta®, Shanghai, China.
- Sodium hydroxide (NaOH) (CAS No: 1310-73-2), Ethanol (EtOH) (CAS No: 64-17-5) were purchased from Energy Chemical, Shanghai, China.
- Palladium(II) acetate, Pd(OAc)2 (CAS No: 3375-31-3), Tetrakis(triphenylphosphine)palladium, Pd(PPh3)4 (CAS No: 14221-01-3), Triphenylphosphine, PPh3 (CAS No: 603-35-0), Dichlorobis(triphenylphosphine)palladium(II) (PdCl2(PPh3)2) (CAS No: 13965-03-2) were purchased from Merck-Sigma, Shanghai, China.
- Potassium iodide (KI) (CAS No: 7681-11-0), N,N-Dimethylformamide (DMF) (CAS No: 68-12-2), Ethylene glycol (EG) (CAS No: 107-21-1), 1,4-Dioxane (CAS No: 123-91-1) were purchased from Acros Organics, NJ, USA.
- Pinacolborane, HB(pin) (CAS No: 25015-63-8), 2,6-Dibromopyridine (CAS No: 626-05-1) were purchased from TCI, Tokyo, Japan.
- All anhydrous solvents were either purchased from Sigma Aldrich, Shanghai, China or Acros Organics Shanghai China or collected from the solvent purification plant at the Center for Supramolecular Chemistry and Catalyses, Shanghai University. All reactions were carried out under an argon atmosphere unless noted otherwise.
- Chromatographic separations were performed by using 100–200 mesh silica gel obtained from Merck-Sigma, Darmstadt, Germany.
- The thin-layer chromatographic (TLC) analyses were carried out using Silica Gel 60 F245 glass sheets, which were used to monitor the progress of the reactions and were purchased from Merck-Sigma, Darmstadt, Germany.
- Final separations of the compounds were performed using a recycling preparative gel permeation chromatography (GPC) from Japan Analytical Industries (JAI), Hiroshima Japan using THF as the mobile phase. The oligopyrrole derivatives 1–9 were synthesized with moderate to good yields by following the procedures in the literature [30,31,32].
3.1.2. Investigation and Characterization
3.2. Synthesis
Synthesis of Acyclic Receptor 10
3.3. Theoretical Calculations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Wang, F.; Liang, K.; Larsen, M.C.; Bähring, S.; Ishida, M.; Furuta, H.; Jana, A. Solvent-Controlled Self-Assembled Oligopyrrolic Receptor. Molecules 2021, 26, 1771. https://doi.org/10.3390/molecules26061771
Wang F, Liang K, Larsen MC, Bähring S, Ishida M, Furuta H, Jana A. Solvent-Controlled Self-Assembled Oligopyrrolic Receptor. Molecules. 2021; 26(6):1771. https://doi.org/10.3390/molecules26061771
Chicago/Turabian StyleWang, Fei, Kejiang Liang, Mads Christian Larsen, Steffen Bähring, Masatoshi Ishida, Hiroyuki Furuta, and Atanu Jana. 2021. "Solvent-Controlled Self-Assembled Oligopyrrolic Receptor" Molecules 26, no. 6: 1771. https://doi.org/10.3390/molecules26061771