Open AccessSynthesis and Reactivity of Triazaphenanthrenes
Author(s) -
Sarah Fernandez,
Maximilian A. Ganiek,
Mariia Karpacheva,
Fabian C. Hanusch,
Stephan Reuter,
Thomas Bein,
Florian Auras,
Paul Knochel
Publication year - 2016
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.6b01373
Subject(s) - chemistry , amination , chloranil , negishi coupling , aromatization , thiophene , quantum yield , reactivity (psychology) , yield (engineering) , furan , nucleophile , photochemistry , ring (chemistry) , organic chemistry , catalysis , medicine , physics , alternative medicine , materials science , pathology , quantum mechanics , metallurgy , fluorescence
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.
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