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

Abstract

The incorporation of Fatoms endows adiethenylbiphenyl-based electron donor with configurational stability and S N Ar reactivity.The former enables the dynamic redoxpair of (R ax )-1/(R ax ,R,R)-1 2+ to exhibit drastic UV/Vis and CD spectral changes upon electrolysis,w hereas the latter makes it possible for (R ax )-1 to serve as au seful chiral synthon for the production of larger assemblies [(R ax ,R ax )-2d,p,m and (R ax ,R ax ,R ax )-3]c ontaining two or three dyrex units.T hese dyads and triad also exhibit aclean electrochiroptical response with isosbestic points owing to one-wave multi-electron transfer.Scheme 1. F-arene based chiral dyrex donor 1 and its stereospecific cyclization to 1 2+ upon 2e-oxidation.