Assembly of an Axially Chiral Dynamic Redox System with a Perfluorobiphenyl Skeleton into Dumbbell- or Tripod-type Electron Donors

Hitomi Tamaoki; Ryo Katoono; Kenshu Fujiwara; Takanori Suzuki

doi:10.1002/anie.201510935

Assembly of an Axially Chiral Dynamic Redox System with a Perfluorobiphenyl Skeleton into Dumbbell- or Tripod-type Electron Donors

Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2582-6. doi: 10.1002/anie.201510935. Epub 2016 Jan 8.

Authors

Hitomi Tamaoki¹, Ryo Katoono¹, Kenshu Fujiwara², Takanori Suzuki³

Affiliations

¹ Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan.
² Faculty of Engineering Science, Akita University, Akita, 010-8052, Japan.
³ Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan. tak@sci.hokudai.ac.jp.

PMID: 26748461
DOI: 10.1002/anie.201510935

Abstract

The incorporation of F atoms endows a diethenylbiphenyl-based electron donor with configurational stability and SN Ar reactivity. The former enables the dynamic redox pair of (Rax)-1/(Rax ,R,R)-1(2+) to exhibit drastic UV/Vis and CD spectral changes upon electrolysis, whereas the latter makes it possible for (Rax)-1 to serve as a useful chiral synthon for the production of larger assemblies [(Rax ,Rax)-2 d,p,m and (Rax ,Rax ,Rax)-3] containing two or three dyrex units. These dyads and triad also exhibit a clean electrochiroptical response with isosbestic points owing to one-wave multi-electron transfer.

Keywords: cationic dye; chirality; electrochromism; fluoroarenes; multielectron transfer.

Publication types

Research Support, Non-U.S. Gov't