pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in Equilibria
Photoresponsive molecular devices can be a valuable tool to promote chemical changes in response to multiple signals, such as photons and pH, to deliver drugs or to detect physiological conditions in vivo. For example, <i>trans</i>-chalcones (<b>Ct</b>) from 4′-hydroxyflavyli...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Colorants |
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| Online Access: | https://www.mdpi.com/2079-6447/2/1/5 |
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| author | Jeonghee Kang Ketevan Basilashvili Barney Yoo Jong I. Lee |
| author_facet | Jeonghee Kang Ketevan Basilashvili Barney Yoo Jong I. Lee |
| author_sort | Jeonghee Kang |
| collection | DOAJ |
| description | Photoresponsive molecular devices can be a valuable tool to promote chemical changes in response to multiple signals, such as photons and pH, to deliver drugs or to detect physiological conditions in vivo. For example, <i>trans</i>-chalcones (<b>Ct</b>) from 4′-hydroxyflavylium (<b>F1</b>) and 7-hydroxyflavylium (<b>F2</b>) can undergo <i>cis-trans</i> isomerization by photoreaction into many different structures. The isomerization takes place at a slow rate in response to pH change; however, it can be done in seconds by photoreaction. In the investigation, as confirming the previous reports, 3-(2-hydroxy-phenyl)-1-(4-hydroxy-phenyl)-propenone, the <i>trans</i>-chalcone (<b>Ct<sub>F1</sub></b>) from <b>F1,</b> produces flavylium ions in pH = 1–4.5. Then, we further discovered that the flavylium quickly releases protons to yield the corresponding quinoidal base (<b>A</b>) in a solution of pH = 5.2 during irradiation with 350 nm. Meanwhile, the photolysis of 3-(2,4-dihydroxy-phenyl)-1-phenyl-propenone, the <i>trans</i>-chalcone (<b>Ct<sub>F2</sub></b>) from <b>F2</b> at pH = 5.6, induces photoacid behavior by losing a proton from the <i>trans</i>-chalcone to generate <b>Ct<sup>2</sup></b><sup>−</sup>. The different outcomes of these nearly colorless chalcones under similar pH conditions and with the same photochemical conditions can be useful when yielding colored <b>AH<sup>+</sup></b>, <b>A</b>, or <b>Ct<sup>2</sup></b><sup>−</sup> in a mildly acidic pH environment with temporal and spatial control using photochemical means. |
| first_indexed | 2024-03-11T06:44:13Z |
| format | Article |
| id | doaj.art-e4aaf88486f142b5a5db5b52817cd0ad |
| institution | Directory Open Access Journal |
| issn | 2079-6447 |
| language | English |
| last_indexed | 2024-03-11T06:44:13Z |
| publishDate | 2023-02-01 |
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| record_format | Article |
| series | Colorants |
| spelling | doaj.art-e4aaf88486f142b5a5db5b52817cd0ad2023-11-17T10:25:30ZengMDPI AGColorants2079-64472023-02-0121587210.3390/colorants2010005pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in EquilibriaJeonghee Kang0Ketevan Basilashvili1Barney Yoo2Jong I. Lee3Department of Chemistry, St. Joseph’s University, 245 Clinton Ave., Brooklyn, NY 11205, USADepartment of Chemistry, St. Joseph’s University, 245 Clinton Ave., Brooklyn, NY 11205, USADepartment of Chemistry, Hunter College-City University of New York, 695 Park Avenue, New York, NY 10065, USADepartment of Chemistry, York College-City University of New York, 94-20 Guy R. Brewer Blvd. Jamaica, New York, NY 11451, USAPhotoresponsive molecular devices can be a valuable tool to promote chemical changes in response to multiple signals, such as photons and pH, to deliver drugs or to detect physiological conditions in vivo. For example, <i>trans</i>-chalcones (<b>Ct</b>) from 4′-hydroxyflavylium (<b>F1</b>) and 7-hydroxyflavylium (<b>F2</b>) can undergo <i>cis-trans</i> isomerization by photoreaction into many different structures. The isomerization takes place at a slow rate in response to pH change; however, it can be done in seconds by photoreaction. In the investigation, as confirming the previous reports, 3-(2-hydroxy-phenyl)-1-(4-hydroxy-phenyl)-propenone, the <i>trans</i>-chalcone (<b>Ct<sub>F1</sub></b>) from <b>F1,</b> produces flavylium ions in pH = 1–4.5. Then, we further discovered that the flavylium quickly releases protons to yield the corresponding quinoidal base (<b>A</b>) in a solution of pH = 5.2 during irradiation with 350 nm. Meanwhile, the photolysis of 3-(2,4-dihydroxy-phenyl)-1-phenyl-propenone, the <i>trans</i>-chalcone (<b>Ct<sub>F2</sub></b>) from <b>F2</b> at pH = 5.6, induces photoacid behavior by losing a proton from the <i>trans</i>-chalcone to generate <b>Ct<sup>2</sup></b><sup>−</sup>. The different outcomes of these nearly colorless chalcones under similar pH conditions and with the same photochemical conditions can be useful when yielding colored <b>AH<sup>+</sup></b>, <b>A</b>, or <b>Ct<sup>2</sup></b><sup>−</sup> in a mildly acidic pH environment with temporal and spatial control using photochemical means.https://www.mdpi.com/2079-6447/2/1/5<i>trans</i>-chalcone<i>cis-trans</i> isomerizationphotoacidflavylium ion |
| spellingShingle | Jeonghee Kang Ketevan Basilashvili Barney Yoo Jong I. Lee pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in Equilibria Colorants <i>trans</i>-chalcone <i>cis-trans</i> isomerization photoacid flavylium ion |
| title | pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in Equilibria |
| title_full | pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in Equilibria |
| title_fullStr | pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in Equilibria |
| title_full_unstemmed | pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in Equilibria |
| title_short | pH-Induced Orthogonal Photoresponse of <i>trans</i>-Chalcone Isomers and Related Compounds in Equilibria |
| title_sort | ph induced orthogonal photoresponse of i trans i chalcone isomers and related compounds in equilibria |
| topic | <i>trans</i>-chalcone <i>cis-trans</i> isomerization photoacid flavylium ion |
| url | https://www.mdpi.com/2079-6447/2/1/5 |
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