One- and two-electron reduction of triarylborane-based helical donor–acceptor compounds

Xiangqing Jia; Jörn Nitsch; Zhu Wu; Alexandra Friedrich; Johannes Krebs; Ivo Krummenacher; Felipe Fantuzzi; Holger Braunschweig; Michael Moos; Christoph Lambert; Bernd Engels; Todd B. Marder

doi:10.1039/D1SC02409D

One- and two-electron reduction of triarylborane-based helical donor–acceptor compounds†‡

Xiangqing Jia,

^a Jörn Nitsch,^a Zhu Wu,^a Alexandra Friedrich,

^a Johannes Krebs,^a Ivo Krummenacher,^a Felipe Fantuzzi,

^ac Holger Braunschweig,

^a Michael Moos,^b Christoph Lambert,

^b Bernd Engels

^c and Todd B. Marder

*^a

Author affiliations

* Corresponding authors

^a Institut für Anorganische Chemie and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
E-mail: todd.marder@uni-wuerzburg.de

^b Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany

^c Institut für Physikalische und Theoretische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany

Abstract

One-electron chemical reduction of 10-(dimesitylboryl)-N,N-di-p-tolylbenzo[c]phenanthrene-4-amine (3-B(Mes)₂-[4]helix-9-N(p-Tol)₂) 1 and 13-(dimesitylboryl)-N,N-di-p-tolyldibenzo[c,g]phenanthrene-8-amine (3-B(Mes)₂-[5]helix-12-N(p-Tol)₂) 2 gives rise to monoanions with extensive delocalization over the annulated helicene rings and the boron p_z orbital. Two-electron chemical reduction of 1 and 2 produces open-shell biradicaloid dianions with temperature-dependent population of the triplet states due to small singlet-triplet gaps. These results have been confirmed by single-crystal X-ray diffraction, EPR and UV/vis-NIR spectroscopy, and DFT calculations.

Chemical Science

One- and two-electron reduction of triarylborane-based helical donor–acceptor compounds†‡

Abstract

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One- and two-electron reduction of triarylborane-based helical donor–acceptor compounds

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