Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Membrane Transport Studies
2.2.1. Investigation of the Influence of Structure on Molecular Recognition
2.2.2. Enantioselective Phase Transport Studies
2.3. Spectrophotometric Investigation of Enantiomeric Recognition
2.4. Development of Enantioselective Potentiometric Sensors
3. Conclusions
4. Experimental
4.1. General
4.2. Synthesis of New Compounds
4.2.1. (2R)-1-(Benzyloxy)dodecan-2-yl-4-Methylbenzene-1-Sulfonate [(R)-4]: See Scheme 1
4.2.2. (2S)-1-(Benzyloxy)dodecan-2-yl-4-Methylbenzene-1-Sulfonate [(S)-4]: See Scheme 1
4.2.3. (8R,16R)-8,16-Bis(decyl)-6,9,12,15,18-Pentaoxa-25-Azatetracyclo [2 1.3.1.05,26.019,24]heptacosa-1,3,5(26),19,21,23-Hexaen-27-one [(R,R)-1]: See Scheme 2
4.2.4. (8S,16S)-8,16-Bis(decyl)-6,9,12,15,18-Pentaoxa-25-Azatetracyclo [21.3.1.05,26.019,24]heptacosa-1,3,5(26),19,21,23-Hexaen-27-one [(S,S)-1]: See Scheme 2
4.2.5. (8R,16R)-8,16-Bis(decyl)-27-Phenyl-6,9,12,15,18-Pentaoxa-25-Azatetracyclo[21.3.1.05,26.019,24]heptacosa-1,3,5(26),19,21,23(27),24-Heptaene [(R,R)-2]: See Scheme 2
Procedure “A”
Procedure “B”
4.2.6. (8S,16S)-8,16-Bis(decyl)-27-Phenyl-6,9,12,15,18-Pentaoxa-25-Azatetracyclo[21.3.1.05,26.019,24]heptacosa-1,3,5(26),19,21,23(27),24-Heptaene [(S,S)-2]: See Scheme 2
Procedure “A”
Procedure “B”
4.3. Transport Studies
4.4. Spectrophotometric Investigations
4.5. Electrochemical Measurements
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the new crown compounds are available from the authors. |
Counter Ions | Transported Amount (%) | Optical Purity (%) |
---|---|---|
acetate | 45 | 5 |
t-butyl sulfonate | 42 | 7 |
chloride | 42 | 7 |
p-toluenesulfonate | 38 | 5 |
Temperature (°C) | Transported Amount (%) | Optical Purity (%) |
---|---|---|
10 | 10 | 68 |
15 | 12 | 62 |
20 | 16 | 53 |
Macrocycle | Ammonium Salts | ΔEMF 1 (mV) | Potentiometric Selectivity 2 | Enantioselectivity 3 | Estimated ΔlogK(R/S) 4 |
---|---|---|---|---|---|
1 | 21 | 2.5 | 0.89 ± 0.02 | 1.12 ± 0.03 | 0.05 ± 0.01 |
1 | 22 | ≈0 | ≈1 | ≈1 | ≈0 |
1 | 23 | ≈0 | ≈1 | ≈1 | ≈0 |
1 | 24 | ≈0 | ≈1 | ≈1 | ≈0 |
2 | 21 | 13.9 | 0.55 ± 0.02 | 1.83 ± 0.07 | 0.26 ± 0.02 |
2 | 22 | 11.3 | 0.60 ± 0.03 | 1.66 ± 0.09 | 0.22 ± 0.02 |
2 | 23 | −13.4 | 1.79 ± 0.10 | 0.56 ± 0.03 | −0.25 ± 0.02 |
2 | 24 | 3.9 | 0.85 ± 0.03 | 1.18 ± 0.05 | 0.07 ± 0.02 |
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Golcs, Á.; Ádám, B.Á.; Horváth, V.; Tóth, T.; Huszthy, P. Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers. Molecules 2020, 25, 2571. https://doi.org/10.3390/molecules25112571
Golcs Á, Ádám BÁ, Horváth V, Tóth T, Huszthy P. Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers. Molecules. 2020; 25(11):2571. https://doi.org/10.3390/molecules25112571
Chicago/Turabian StyleGolcs, Ádám, Bálint Árpád Ádám, Viola Horváth, Tünde Tóth, and Péter Huszthy. 2020. "Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers" Molecules 25, no. 11: 2571. https://doi.org/10.3390/molecules25112571