Synthesis, photophysical and electronic properties of tetra-donor- or acceptor-substituted ortho-perylenes displaying four reversible oxidations or reductions.

ABSTRACT: Via regioselective Ir-catalyzed C-H borylation and subsequent reactions (i.e., via Br₄-Per or (BF₃K)₄-Per intermediates), we have introduced strong π-donors and acceptors at the 2,5,8,11-positions of perylene leading to unusual properties. Thus, incorporation of four donor diphenylamine (DPA) or four acceptor Bmes₂ (mes = 2,4,6-Me₃C₆H₂) moieties yields novel compounds which can be reversibly oxidized or reduced four times, respectively, an unprecedented behavior for monomeric perylene derivatives. Spectroelectrochemical measurements show NIR absorptions up to 3000 nm for the mono-cation radical of (DPA)₄-Per and a strong electronic coupling over the perylene bri

SUBMITTER: Merz J 

PROVIDER: S-EPMC6761871 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature