The role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivatives
Abstract We report the electronic absorption spectroscopy of 7,7,8,8-tetracyanoquinodimethane (TCNQ) and its fluorinated derivatives (F2TCNQ and F4TCNQ), well-known electron-accepting molecules in common organic solvents (toluene, chlorobenzene, acetonitrile, and ethanol) under controlled exposure t...
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| Format: | Article |
| Language: | English |
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SpringerOpen
2023-01-01
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| Series: | Journal of Analytical Science and Technology |
| Subjects: | |
| Online Access: | https://doi.org/10.1186/s40543-022-00364-z |
| _version_ | 1797952507799928832 |
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| author | Jieun Bang JaeHong Park |
| author_facet | Jieun Bang JaeHong Park |
| author_sort | Jieun Bang |
| collection | DOAJ |
| description | Abstract We report the electronic absorption spectroscopy of 7,7,8,8-tetracyanoquinodimethane (TCNQ) and its fluorinated derivatives (F2TCNQ and F4TCNQ), well-known electron-accepting molecules in common organic solvents (toluene, chlorobenzene, acetonitrile, and ethanol) under controlled exposure to air (O2) and UV light. All compounds (FxTCNQ (x = 0, 2, 4)) were stable in a neutral state (FxTCNQ0) in toluene and chlorobenzene, even under both O2 and UV light. On the other hand, in EtOH, the formation of FxTCNQ·− was monitored upon controlled exposure to O2 or UV light. Especially in air-equilibrated ethanol upon the UV-illumination, efficient α,α-dicyano-p-toluoylcyanide anion (DCTC−) and its fluorinated derivatives were generated evinced by the absorption peak near 480 nm, whereas the reaction was shut off by removing O2 or blocking UV light, thereby keeping FxTCNQ·− stable. However, even in deaerated ethanol, upon the UV-illumination, the anion formation of TCNQ and its fluorinated derivatives (FxTCNQ·−, x = 0, 2, 4) was inevitable, showing the stability of FxTCNQ0 depends on the choice of solvent. |
| first_indexed | 2024-04-10T22:47:27Z |
| format | Article |
| id | doaj.art-b97144c944664e019c9b5ef00e747918 |
| institution | Directory Open Access Journal |
| issn | 2093-3371 |
| language | English |
| last_indexed | 2024-04-10T22:47:27Z |
| publishDate | 2023-01-01 |
| publisher | SpringerOpen |
| record_format | Article |
| series | Journal of Analytical Science and Technology |
| spelling | doaj.art-b97144c944664e019c9b5ef00e7479182023-01-15T12:14:13ZengSpringerOpenJournal of Analytical Science and Technology2093-33712023-01-011411610.1186/s40543-022-00364-zThe role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivativesJieun Bang0JaeHong Park1Department of Chemistry and Nanoscience, Ewha Womans UniversityDepartment of Chemistry and Nanoscience, Ewha Womans UniversityAbstract We report the electronic absorption spectroscopy of 7,7,8,8-tetracyanoquinodimethane (TCNQ) and its fluorinated derivatives (F2TCNQ and F4TCNQ), well-known electron-accepting molecules in common organic solvents (toluene, chlorobenzene, acetonitrile, and ethanol) under controlled exposure to air (O2) and UV light. All compounds (FxTCNQ (x = 0, 2, 4)) were stable in a neutral state (FxTCNQ0) in toluene and chlorobenzene, even under both O2 and UV light. On the other hand, in EtOH, the formation of FxTCNQ·− was monitored upon controlled exposure to O2 or UV light. Especially in air-equilibrated ethanol upon the UV-illumination, efficient α,α-dicyano-p-toluoylcyanide anion (DCTC−) and its fluorinated derivatives were generated evinced by the absorption peak near 480 nm, whereas the reaction was shut off by removing O2 or blocking UV light, thereby keeping FxTCNQ·− stable. However, even in deaerated ethanol, upon the UV-illumination, the anion formation of TCNQ and its fluorinated derivatives (FxTCNQ·−, x = 0, 2, 4) was inevitable, showing the stability of FxTCNQ0 depends on the choice of solvent.https://doi.org/10.1186/s40543-022-00364-zElectron acceptorPhotochemistryRadical anionTetracyanoquinodimethane |
| spellingShingle | Jieun Bang JaeHong Park The role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivatives Journal of Analytical Science and Technology Electron acceptor Photochemistry Radical anion Tetracyanoquinodimethane |
| title | The role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivatives |
| title_full | The role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivatives |
| title_fullStr | The role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivatives |
| title_full_unstemmed | The role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivatives |
| title_short | The role of molecular oxygen (O2) and UV light in the anion radical formation and stability of TCNQ and its fluorinated derivatives |
| title_sort | role of molecular oxygen o2 and uv light in the anion radical formation and stability of tcnq and its fluorinated derivatives |
| topic | Electron acceptor Photochemistry Radical anion Tetracyanoquinodimethane |
| url | https://doi.org/10.1186/s40543-022-00364-z |
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