Highly Efficient, Tripodal Ion-Pair Receptors for Switching Selectivity between Acetates and Sulfates Using Solid–Liquid and Liquid–Liquid Extractions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Receptor Design and Synthesis
2.2. Binding Studies
2.3. Extraction Studies
2.4. Crystallization and Single-Crystal X-ray Diffraction
3. Materials and Methods
3.1. General Methods
3.2. Synthetic Details
- HRMS (ESI): calculated for C15H21N9 (M + H) + 327.1909, found: 327.1915.
- 1H NMR (300 MHz, CDCl3) δ 4.50 (s, 6H), 2.84 (q, 6H), 1.25 (t, 9H).
- 13C NMR (75 MHz, CDCl3) δ 145.0, 129.8, 47.9, 23.2 15.8.
- HRMS (ESI): calculated for C15H27N3 (M + H) + 250.2283, found: 250.2290.
- 1H NMR (300 MHz, CDCl3) δ 3.85 (s, 6H), 2.80 (q, 6H), 1.40 (s, 6H), 1.25 (t, 9H).
- 13C NMR (75 MHz, CDCl3) δ 140.4, 137.5, 39.7, 22.5, 16.8.
- HRMS (ESI): calculated for C21H27NO9Na (M + Na)+: 460.1584, found: 460.1588.
- 1H NMR (300 MHz, DMSO-d6) δ 10.64 (s, 1H), 7.18–6.96 (m, 1H), 6.96–6.84 (m, 1H), 6.83–6.78 (m, 1H), 4.34 (s, 3H), 4.10–3.95 (m, 4H), 3.80–3.65 (m, 4H), 3.62–3.44 (m, 12H).
- 13C NMR (75 MHz, DMSO-d6) δ 189.3, 184.1, 178.9, 169.1, 148.9, 145.6, 132.0, 114.0, 112.1, 106.7, 70.5, 70.3, 70.2, 69.6, 69.4, 69.1, 68.7, 61.0.
- HRMS (ESI): calculated for C13H13NO5Na (M + Na)+: 286.0692, found: 286.0702.
- u1H NMR (300 MHz, DMSO-d6) δ 10.63 (s, 1H), 7.20–6.65 (m, 3H), 4.37 (s, 3H), 3.85–3.65 (m, 6H).
- 13C NMR (75 MHz, DMSO-d6) δ 189.1, 183.8, 178.6, 169.2, 149.4, 146.2, 131.8, 112.6, 111.9, 105.3, 60.9, 56.2, 55.9.
- HRMS (ESI): calculated for C75H96N6O24Na (M + Na)+:1487.6373, found: 1487.6333.
- 1H NMR (300 MHz, DMSO-d6) δ 9.43 (s, 1H), 7.59 (s, 1H), 7.30 (s, 1H), 6.92–6.73 (m, 2H), 4.98 (s, 2H), 4.12–4.00 (m, 4H), 3.80–3.72 (m, 4H), 3.62–3.50 (m, 12H), 2.85 (s, 2H), 1.19 (m, 3H).
- 13C NMR (75 MHz, DMSO-d6) δ 183.8, 180.7, 168.5, 163.9, 148.6, 144.4, 144.0, 133.1, 132.5, 113.3, 110.0, 104.3, 70.0, 69.9, 69.0, 68.8, 67.9, 67.7, 65.4, 42.0, 23.1, 16.8.
- HRMS (ESI): calculated for C51H54N6O12Na (M + Na)+: 965.3698, found: 965.3712.
- 1H NMR (300 MHz, DMSO-d6) δ 9.44 (s, 1H), 7.59 (s, 1H), 7.31 (s, 1H), 6.94-6.76 (m, 2H), 4.99 (s, 2H), 3.79–3.68 (m, 6H), 2.88–2.84 (m, 2H), 1.19 (m, 3H).
- 13C NMR (75 MHz, DMSO-d6) δ 183.7, 180.7, 168.4, 163.9, 149.8, 145.1, 144.3, 133.1, 132.6, 113.1, 109.9, 103.9, 56.3, 55.9, 42.0, 23.1, 16.8.
- HRMS (ESI): calculated for C27H32N2O8Na (M + Na)+: 535.2056, found: 535.2043.
- 1H NMR (300 MHz, DMSO-d6) δ 9.56 (s, 1H), 7.90 (s, 1H), 7.45–7.30 (m, 5H), 7.23 (s, 1H), 7.00–6.80 (m, 1H), 6.80–6.71 (m, 1H), 4.80 (s, 2H), 4.12–3.95 (m, 4H), 3.79–3.68 (m, 4H), 3.66–3.49 (m, 12 H).
- 13C NMR (75 MHz, DMSO-d6) δ 183.9, 181.2, 168.9, 164.2, 149.2, 144.6, 139.0, 133.1, 129.2, 128.1, 128.1, 114.5, 110.4, 105.1, 70.3, 69.2, 69.1, 69.0, 68.4, 47.6.
3.3. NMR Titration Procedure
3.4. UV-Vis Titration Procedure
3.5. Crystallographic Measurements
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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1 | 1 + 3 Equivalent K+ | KK+/KTBA- | |
---|---|---|---|
Cl− | 283 | 373 | 1.32 |
Br− | 40 | 100 | 2.50 |
NO2− | 59 | 101 | 1.71 |
NO3− (b) | − | − | - |
PhCOO− | 415 | 500 | 1.20 |
CH3COO− | 400 | 453 | 1.13 |
SO42− (c) | − | - | - |
H2PO4− (c) | - | - | - |
1 | 1 + 3 equiv. K+ | KK+/KTBA− | |
---|---|---|---|
Cl− | 3.68 × 104 | 4.60 × 104 | 1.25 |
Br− | 2.27 × 104 | 3.61 × 104 | 1.60 |
NO2− | 2.16 × 104 | 3.55 × 104 | 1.65 |
NO3− | 5.26 × 103 | 7.84 × 103 | 1.49 |
PhCOO− | 8.40 × 104 | 9.02 × 104 | 1.07 |
CH3COO− | 6.14 × 104 | 7.59 × 104 | 1.24 |
SO42− (b) | - | - | - |
H2PO4− (b) | - | - | - |
Formula | C102.01H140.02F6.91N7.59Na2.30O39.28, corresponding to approx.: 1 + 2.30 × (sodium trifluoroacetate) + 4.61 × (ethyl acetate) + 1.58 × acetonitrile + 0.80 × methanol * + 0.65 × H2O* |
---|---|
Mx/g∙mol−1 | 2288.94 |
T/K | 130.0(5) |
λ/Å | 0.71073 |
Crystal size | 0.086 × 0.307 × 0.569 |
Space group | P1 |
Unit cell dimensions | a = 13.9030(10) Å α = 106.491(2)° b = 19.1752(13) Å β = 98.390(2)° c = 24.2017(16) Å γ = 105.570(2)° |
V/Å3, Z | 5784.7(7), 2 |
Dx/g∙cm−3 | 1.312 |
μ/mm−1 | 0.114 |
F(000) | 2414 |
θmin, θmax | 2.86°, 25.05° |
Index ranges (merged data) | −16 ≤ h ≤ 16, −23 ≤ k ≤ 22, 0 ≤ l ≤ 29 |
Reflections collected/independent | 208133/ 21096 ** Rint = 0.0674 ** |
Completeness | 99.1% |
Absorption correction | Multi-Scan |
Tmax, Tmin | 0.990, 0.938 |
Structure solution technique | direct methods |
Refinement method | Full-matrix LSQ on F2 |
Data/restraints/parameters | 20322/603/1807 |
GOF on F2 | 1.051 |
Final R indices | 13630 data; I > 2σ(I) R1 = 0.0699, wR2 = 0.1894 all data R1 = 0.1085, wR2 = 0.2084 |
Extinction coefficient | 0.0013(4) |
Δρmax, Δρmin | 0.397, −0.396 e∙Å−3 |
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Zaleskaya, M.; Dobrzycki, Ł.; Romański, J. Highly Efficient, Tripodal Ion-Pair Receptors for Switching Selectivity between Acetates and Sulfates Using Solid–Liquid and Liquid–Liquid Extractions. Int. J. Mol. Sci. 2020, 21, 9465. https://doi.org/10.3390/ijms21249465
Zaleskaya M, Dobrzycki Ł, Romański J. Highly Efficient, Tripodal Ion-Pair Receptors for Switching Selectivity between Acetates and Sulfates Using Solid–Liquid and Liquid–Liquid Extractions. International Journal of Molecular Sciences. 2020; 21(24):9465. https://doi.org/10.3390/ijms21249465
Chicago/Turabian StyleZaleskaya, Marta, Łukasz Dobrzycki, and Jan Romański. 2020. "Highly Efficient, Tripodal Ion-Pair Receptors for Switching Selectivity between Acetates and Sulfates Using Solid–Liquid and Liquid–Liquid Extractions" International Journal of Molecular Sciences 21, no. 24: 9465. https://doi.org/10.3390/ijms21249465