Synthesis and Electronic Properties of Fluoreno[2,1-a]fluorenedione and Fluoreno[1,2-a]fluorenedione
| Autor: | James E. Wood, Allison S. Hacker, Chad E. Immoos, Hannah Hashimoto, Derik K. Frantz, Mauricio Pavano, Sam P. Genis |
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| Rok vydání: | 2017 |
| Předmět: |
Molecular orbital energy
Absorption spectroscopy 010405 organic chemistry Organic Chemistry Protonation Sulfuric acid 010402 general chemistry 01 natural sciences 0104 chemical sciences Acylation chemistry.chemical_compound chemistry Intramolecular force Physical chemistry Cyclic voltammetry Electronic properties |
| Zdroj: | The Journal of organic chemistry. 83(1) |
| ISSN: | 1520-6904 |
| Popis: | The [2,1-a]- and [1,2-a]-isomers of fluorenofluorenedione have been synthesized via intramolecular Friedel-Crafts acylations. DFT calculations indicate that the [1,2-a]-isomer adopts a twisted, helical C2-symmetric structure and that its protonated form is the thermodynamic product of the Friedel-Crafts acylation in hot sulfuric acid. Absorption spectroscopy and cyclic voltammetry measurements provide experimental estimations of frontier molecular orbital energy levels, which are reported and discussed. |
| Databáze: | OpenAIRE |
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