Heptacene
| Heptacene | |
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heptacene |
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| Identifiers | |
| CAS number | 258-38-8 |
| PubChem | 5460712 |
| ChemSpider | 4574185 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C30H18 |
| Molar mass | 378.46 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Heptacene is an organic compound and a polycyclic aromatic hydrocarbon and the seventh member of the acene or polyacene family of linear fused benzene rings.[1] This compound has long been pursued by chemists because of its potential interest in electronic applications and was first synthesized but not isolated in 2006.[2][3]
The final step is a photochemical decarbonylization with a 1,2-dione bridge extruded as carbon monoxide. In solution heptacene is not formed because it is very unstable being a reactive DA diene and quickly reacts with oxygen or forms dimers. When on the other hand the dione precursor is dissolved in a PMMA matrix first, heptacene can be studied by spectroscopy.
7,16-Bis(tris(trimethylsilyl)silylethynyl)heptacene was synthesised in 2005.[4] This compound is stable in the solid state for a week but decomposes in contact with air. Its synthesis started from anthraquinone and naphthalene-2,3-dicarboxaldehyde. More stable substituted heptacenes have been reported: with stabilizing p-(t-butyl)thiophenyl substituents[5] and with phenyl and triisopropylsilylethynyl groups.[6]
[edit] References
- ^ Zade, Sanjio S.; Bendikov, Michael (2010). "Heptacene and Beyond: the Longest Characterized Acenes". Angewandte Chemie International Edition 49 (24): n/a. doi:10.1002/anie.200906002. PMID 20468014.
- ^ Photogeneration of Heptacene in a Polymer Matrix Rajib Mondal, Bipin K. Shah, and Douglas C. Neckers J. Am. Chem. Soc.; 2006; 128(30) pp 9612 - 9613; (Communication) doi:10.1021/ja063823i
- ^ a| Diels-Alder reaction of dibromonaphthalene forming a naphthyne and bicyclo[2,2,2]oct-2,3,5,6,7-pentaene with n-butyllithium in toluene 3 hours at -50 to -60°C 53% chemical yield b| organic oxidation with P-chloranil in toluene 2 hours reflux and 81% yield c] Bishydroxylation with N-Methylmorpholine N-oxide and osmium tetroxide in acetone and t-butanol at room temperature for 48 hours, 83% yield d] Swern oxidation with trifluoroacetic acid in dimethyl sulfoxide and dichloromethane at -78°C, 51% yield e] photochemical decarbonylization in a PMMA matrix at 395 nm
- ^ Payne, Marcia M.; Parkin, Sean R.; Anthony, John E. (2005). "Functionalized Higher Acenes: Hexacene and Heptacene". Journal of the American Chemical Society 127 (22): 8028. doi:10.1021/ja051798v. PMID 15926823.
- ^ Kaur, Irvinder; Stein, Nathan N.; Kopreski, Ryan P.; Miller, Glen P. (2009). "Exploiting Substituent Effects for the Synthesis of a Photooxidatively Resistant Heptacene Derivative". Journal of the American Chemical Society 131 (10): 3424. doi:10.1021/ja808881x. PMID 19243093.
- ^ Chun, Doris; Cheng, Yang; Wudl, Fred (2008). "The Most Stable and Fully Characterized Functionalized Heptacene". Angewandte Chemie International Edition 47 (44): 8380. doi:10.1002/anie.200803345. PMID 18825763.
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