Spin-carrying benzoquinone derivatives

The Journal of Organic Chemistry
Shin'ichi NakatsujiJun-ichi Yamada

Abstract

Several 1,4-benzoquinone derivatives carrying oxy-TEMPO radical(s) at the 2-position or 2,5-positions were found to give black crystals by recrystallization from pale yellow solutions and it was revealed from their crystal structures that unusual single-component CT complexes were formed, in which a nitroxide moiety plays the roll of a donor part and a 1,4-benzoquinone group of the same molecule works as an acceptor part, respectively. On the contrary, no CT formation was found for the derivatives carrying oxy-TEMPO radicals at 2,6-positions and one of the TEMPO groups contributes to a CT formation in a 1,4-benzoquinone derivative carrying amino-TEMPO radicals at 2,5-positions derived from fluoranil, while the other one has a close oxygen-to-oxygen contact with another neighboring molecule to give a very large exchange coupling of J/k(B) = -154 K.

Citations

Jul 16, 2011·Chemical Biology & Drug Design·Komala PanduranganGrace G Morgan
Aug 16, 2013·Beilstein Journal of Organic Chemistry·Hideto SuzukiShin'ichi Nakatsuji
Jun 19, 2014·Acta Crystallographica. Section E, Structure Reports Online·Ersin OrhanBruno Therrien
Nov 16, 2018·The Journal of Organic Chemistry·Sophie Langis-BarsettiJames D Wuest

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