Synthesis and Reactivity of Triazaphenanthrenes

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• 作者：Sarah Fernandez ; Maximilian A. Ganiek ; Mariia Karpacheva ; Fabian C. Hanusch ; Stephan Reuter ; Thomas Bein ; Florian Auras ; Paul Knochel
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3158-3161
• 全文大小：379K
• 年卷期：0
• ISSN：1523-7052

文摘

Pyridonaphthyridines (triazaphenanthrenes) were prepared in 4 steps and in 13–52% overall yield using Negishi cross-couplings between iodopicolines and 2-chloro-pyridylzinc derivatives. After chlorination, Gabriel amination and spontaneous ring-closure, the final aromatization leading to the triazaphenanthrenes was achieved with chloranil. This heterocyclic scaffold underwent a nucleophilic addition at position 6 leading to further functionalized pyridonaphthyridines. The influence of these chemical modifications on the optical properties was studied by steady-state and time-resolved optical spectroscopy. While the thiophene-substituted heterocycles exhibited the most extended absorption, the phenyl- and furan-substituted compounds showed a stronger photoluminescence, reaching above 20% quantum yield and lifetimes of several nanoseconds.