meso-Substituted Bisanthenes as Soluble and Stable Near-infrared Dyes
Three meso-substituted bisanthenes, 4−6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moder...
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| Published in | Journal of organic chemistry Vol. 75; no. 3; pp. 856 - 863 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
05.02.2010
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-3263 1520-6904 1520-6904 |
| DOI | 10.1021/jo902413h |
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| Abstract | Three meso-substituted bisanthenes, 4−6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4−6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. |
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| AbstractList | Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone pi-stacking motif in the single crystal. Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone pi-stacking motif in the single crystal.Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone pi-stacking motif in the single crystal. Three meso-substituted bisanthenes, 4−6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4−6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. |
| Author | Wu, Jishan Huang, Kuo-Wei Li, Jinling Chi, Chunyan Zhang, Kai Zhang, Xiaojie |
| Author_xml | – sequence: 1 givenname: Jinling surname: Li fullname: Li, Jinling – sequence: 2 givenname: Kai surname: Zhang fullname: Zhang, Kai – sequence: 3 givenname: Xiaojie surname: Zhang fullname: Zhang, Xiaojie – sequence: 4 givenname: Kuo-Wei surname: Huang fullname: Huang, Kuo-Wei – sequence: 5 givenname: Chunyan surname: Chi fullname: Chi, Chunyan – sequence: 6 givenname: Jishan surname: Wu fullname: Wu, Jishan email: chmwuj@nus.edu.sg |
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| Keywords | ACENES GROUND-STATE WAVELENGTHS AGENTS PENTACENES DERIVATIVES ELECTRONICS Amphoteric Dyes Stability Hydrocarbon Solubility Polycyclic aromatic compound Quantum yield Thermal stability Near infrared radiation Chemical reduction Cyclic voltammetry Near infrared spectrometry Anions Fluorescence yield Pi-System Electrochemistry Photochemical stability Soluble compound Cations Oxidation Redox system Chemical synthesis Crystalline structure |
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| Snippet | Three meso-substituted bisanthenes, 4−6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and... Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and... |
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| SubjectTerms | Anthracenes - chemical synthesis Anthracenes - chemistry Chemistry Chemistry, Organic Coloring Agents - chemistry Condensed benzenic and aromatic compounds Crystallography, X-Ray Electrochemistry Exact sciences and technology General and physical chemistry Molecular Structure Organic chemistry Physical Sciences Preparations and properties Science & Technology Solubility Spectroscopy, Near-Infrared |
| Title | meso-Substituted Bisanthenes as Soluble and Stable Near-infrared Dyes |
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