Synthesis and properties of fully conjugated indacenediselenophene and diindenoselenophene derivatives. Issue 23 (3rd June 2015)

• Record Type: Journal Article
• Authors: Marshall, Jonathan L.; Rudebusch, Gabriel E.; Vonnegut, Chris L.; Zakharov, Lev N.; Haley, Michael M.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 23(2015)
• Page Start: 3235
• Page End: 3239
• Publication Date: 2015-06-03
• Subjects: Selenophene -- Indenofluorene -- Quinodimethane -- Polycyclic aromatics -- Organic electronics; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.12.096
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The synthesis and characterization of indacenediselenophene (IDS) and diindenoselenophene (DIS), the selenophene-containing analogues of indacenedithiophene (IDT) and diindenothiophene (DIT), respectively, are described. Cyclic voltammetry reveals that IDS and DIS both undergo two one-electron reductions and a one-electron oxidation and have narrower HOMO/LUMO energy gaps when compared to their thiophene-containing counterparts. The UV–Vis spectrum of IDS exhibits a red-shifted absorbance maximum with respect to the sulfur-containing IDT, and single crystal XRD shows close C–Se contacts of 3.407 Å (IDS) and close C–C contacts of 3.358 Å (DIS).