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Assembly of an Axially Chiral Dynamic Redox System with a Perfluorobiphenyl Skeleton into Dumbbell‐ or Tripod‐type Electron Donors
Author(s) -
Tamaoki Hitomi,
Katoono Ryo,
Fujiwara Kenshu,
Suzuki Takanori
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201510935
Subject(s) - synthon , dumbbell , redox , tripod (photography) , chemistry , triad (sociology) , electron transfer , axial symmetry , electron , crystallography , stereochemistry , photochemistry , physics , inorganic chemistry , medicine , psychology , quantum mechanics , psychoanalysis , optics , physical therapy
Abstract The incorporation of F atoms endows a diethenylbiphenyl‐based electron donor with configurational stability and S N Ar reactivity. The former enables the dynamic redox pair of ( R ax )‐ 1 /( R ax , R , R )‐ 1 2+ to exhibit drastic UV/Vis and CD spectral changes upon electrolysis, whereas the latter makes it possible for ( R ax )‐ 1 to serve as a useful chiral synthon for the production of larger assemblies [( R ax , R ax )‐ 2 d,p,m and ( R ax , R ax , R ax )‐ 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.