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Unexpected One‐Pot Synthesis of Diindolotriazatruxene: A Planar Electron‐Rich Scaffold Toward Highly π‐Extended PAHs

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A unique planar and highly π-extended scaffold, 3,8,14,19-tetrabromo-diindolotriazatruxene (4Br-DIT), was synthesized for the first time by a facile one-pot strategy. The structure of 4Br-DIT was adequately verified by MALDI-TOF mass… Click to show full abstract

A unique planar and highly π-extended scaffold, 3,8,14,19-tetrabromo-diindolotriazatruxene (4Br-DIT), was synthesized for the first time by a facile one-pot strategy. The structure of 4Br-DIT was adequately verified by MALDI-TOF mass spectrometry, 1H and 13C NMR, and single-crystal X-ray diffraction. A combination of thermal, optical, and electrochemical investigation confirmed the electron-rich characteristics of the resulting diindolotriazatruxene unit, demonstrating the promise as a novel building block to construct highly π-extended polycyclic aromatic hydrocarbons (PAHs).

Keywords: planar; electron rich; highly extended; diindolotriazatruxene; one pot

Journal Title: Asian Journal of Organic Chemistry
Year Published: 2017

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