2019年11月15日
Syntheses and properties of linear π-conjugated molecules composed of 1-azaazulene and azulene
Tetrahedron
- ,
- ,
- ,
- ,
- ,
- 巻
- 75
- 号
- 46
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1016/j.tet.2019.130658
© 2019 Elsevier Ltd Two compounds, 6-(1-azaazulen-2-yl)ethynylazulene (8) and 6-(2-azulenyl)ethynylazulene (10), were synthesized using the Sonogashira-Hagihara cross-coupling reaction followed by decarboxylation with concentrated phosphoric acid. Compounds 8 and 10 were characterized by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, ultraviolet–visible (UV–Vis) spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations. Based on the results, both compounds were confirmed to have π-conjugation throughout their molecular structures. The acidic responsivity of compounds 8 and 10 was evaluated using UV–Vis and 1H NMR spectroscopy. Compound 8 was found to be highly sensitive to trifluoroacetic acid, with its 1-azaazulenyl moiety acting as a base. Compound 10 generated azulenium cations when mixed with excess amounts of trifluoroacetic acid.
- リンク情報
- ID情報
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- DOI : 10.1016/j.tet.2019.130658
- ISSN : 0040-4020
- eISSN : 1464-5416
- SCOPUS ID : 85073012709