Cover Image

The radical anion and dianion of Benzo(3,4)cyclobuta(1,2-b)phenazine

We present the reduction of two azaacenes (a benzo-[3,4]cyclobuta[1,2-b]phenazine and a benzo[3,4]cyclobuta[1,2-b]naphtho[2,3-i]phenazine derivative), featuring a single cyclobutadiene unit, to their radical anions and dianions. The reduced species were produced using potassium naphthalenide in the...

Full description

Saved in:
Bibliographic Details
Main Authors: Wu, Zhu (Author) , Hippchen, Nikolai (Author) , Han, Jie (Author) , Ji, Lei (Author) , Friedrich, Alexandra (Author) , Krummenacher, Ivo (Author) , Braunschweig, Holger (Author) , Krebs, Johannes (Author) , Moos, Michael (Author) , Biegger, Philipp (Author) , Tverskoy, Olena (Author) , Maier, Steffen (Author) , Lambert, Christoph (Author) , Dreuw, Andreas (Author) , Marder, Todd B. (Author) , Freudenberg, Jan (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: February 21, 2023
In: The journal of organic chemistry
Year: 2023, Pages: 1-8
ISSN:1520-6904
DOI:10.1021/acs.joc.2c02279
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.2c02279
Get full text
Author Notes:Zhu Wu, Nikolai Hippchen, Jie Han, Lei Ji, Alexandra Friedrich, Ivo Krummenacher, Holger Braunschweig, Johannes Krebs, Michael Moos, Philipp Biegger, Olena Tverskoy, Steffen Maier, Christoph Lambert, Andreas Dreuw, Todd B. Marder, Jan Freudenberg, and Uwe H.F. Bunz
Description
Summary:We present the reduction of two azaacenes (a benzo-[3,4]cyclobuta[1,2-b]phenazine and a benzo[3,4]cyclobuta[1,2-b]naphtho[2,3-i]phenazine derivative), featuring a single cyclobutadiene unit, to their radical anions and dianions. The reduced species were produced using potassium naphthalenide in the presence of 18-crown-6 in THF. Crystal structures of the reduced representatives were obtained and their optoelectronic properties evaluated. Charging these 4n Hückel systems gives dianionic 4n + 2 π-electron systems with increased antiaromaticity, according to NICS(1.7)zz calculations, featuring unusually red-shifted absorption spectra.
Item Description:Im Titel steh [3,4] und [1,2-b] jeweils in eckiger Klammer
Gesehen am 27.02.2023
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/acs.joc.2c02279

Similar Items