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

Tamaoki Hitomi | Zendy; Katoono Ryo | Zendy; Fujiwara Kenshu | Zendy; Suzuki Takanori | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201510935

Subject(s) - synthon , chemistry , tripod (photography) , redox , dumbbell , triad (sociology) , electron transfer , destabilisation , electron , stereochemistry , crystallography , photochemistry , organic chemistry , physics , medicine , psychology , social psychology , quantum mechanics , psychoanalysis , optics , physical therapy

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.

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