Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers
New highly lipophilic enantiopure crown ethers containing a heterocyclic unit have been synthesized. Phase transport, UV-Vis- and fluorescence spectrophotometric investigations as well as electrochemical studies on the complexation of the new macrocycles with several amine and amino acid derivatives...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/11/2571 |
| _version_ | 1797566536911683584 |
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| author | Ádám Golcs Bálint Árpád Ádám Viola Horváth Tünde Tóth Péter Huszthy |
| author_facet | Ádám Golcs Bálint Árpád Ádám Viola Horváth Tünde Tóth Péter Huszthy |
| author_sort | Ádám Golcs |
| collection | DOAJ |
| description | New highly lipophilic enantiopure crown ethers containing a heterocyclic unit have been synthesized. Phase transport, UV-Vis- and fluorescence spectrophotometric investigations as well as electrochemical studies on the complexation of the new macrocycles with several amine and amino acid derivatives were also carried out. Achiral amines were used for studying the structural preference of the new macrocycles. Among the studied structural features of the guest molecules, the intermolecular <i>π</i>-<i>π</i> interaction showed the most significant effect on complexation, which made the aralkylamine-type compounds the most preferable guest molecules. The studied liquid membrane-based applications and photophysical investigations showed appreciable enantiomeric recognition toward some aralkylamine model compounds with homochiral preferences. New crown ether derivatives (<i>R</i>,<i>R</i>)-<b>2</b> and (<i>S</i>,<i>S</i>)-<b>2</b> were successfully applied as enantioselective carrier and sensor molecules. |
| first_indexed | 2024-03-10T19:28:16Z |
| format | Article |
| id | doaj.art-f57dc4adbfa845ef8bfe5ea6068a32bc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:28:16Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f57dc4adbfa845ef8bfe5ea6068a32bc2023-11-20T02:24:27ZengMDPI AGMolecules1420-30492020-05-012511257110.3390/molecules25112571Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown EthersÁdám Golcs0Bálint Árpád Ádám1Viola Horváth2Tünde Tóth3Péter Huszthy4Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., H-1111 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., H-1111 Budapest, HungaryMTA-BME Computation Driven Chemistry Research Group, Szent Gellért tér 4., H-1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., H-1111 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., H-1111 Budapest, HungaryNew highly lipophilic enantiopure crown ethers containing a heterocyclic unit have been synthesized. Phase transport, UV-Vis- and fluorescence spectrophotometric investigations as well as electrochemical studies on the complexation of the new macrocycles with several amine and amino acid derivatives were also carried out. Achiral amines were used for studying the structural preference of the new macrocycles. Among the studied structural features of the guest molecules, the intermolecular <i>π</i>-<i>π</i> interaction showed the most significant effect on complexation, which made the aralkylamine-type compounds the most preferable guest molecules. The studied liquid membrane-based applications and photophysical investigations showed appreciable enantiomeric recognition toward some aralkylamine model compounds with homochiral preferences. New crown ether derivatives (<i>R</i>,<i>R</i>)-<b>2</b> and (<i>S</i>,<i>S</i>)-<b>2</b> were successfully applied as enantioselective carrier and sensor molecules.https://www.mdpi.com/1420-3049/25/11/2571chiralityion-selective electrodemacrocyclesmembrane transportmolecular recognition |
| spellingShingle | Ádám Golcs Bálint Árpád Ádám Viola Horváth Tünde Tóth Péter Huszthy Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers Molecules chirality ion-selective electrode macrocycles membrane transport molecular recognition |
| title | Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers |
| title_full | Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers |
| title_fullStr | Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers |
| title_full_unstemmed | Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers |
| title_short | Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers |
| title_sort | synthesis molecular recognition study and liquid membrane based applications of highly lipophilic enantiopure acridino crown ethers |
| topic | chirality ion-selective electrode macrocycles membrane transport molecular recognition |
| url | https://www.mdpi.com/1420-3049/25/11/2571 |
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