title: Tellurophenes with delocalized π-systems and their extended valence adducts.
abstract: The π-conjugated 2,5-substituted tellurophene compounds 2,5-bis(2-(9,9-dihexylfluorene))tellurophene (1) and 2,5-diphenyltellurophene (3) were synthesized through ring closing reactions of 1,4-substituted butadiyne. The oxidative addition of Br(2) to tellurophene compounds 1 and 3 was studied through absorption spectroscopy, NMR, electrochemistry, X-ray crystallography, and density functional theory (DFT) calculations. When Br(2) adds to the tellurium center the absorption spectrum shifts to a lower energy. From electrochemistry and DFT calculations we show that this is caused by lowering the lowest unoccupied orbital. The highest occupied orbital is also lowered, but to a lesser extent. This shift in absorption spectrum and lowering of the oxidation potential can provide a method to modify tellurophene containing materials. The two-electron oxidative addition is promising for catalyzing energy storage reactions.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada.
authors.forename: Theresa M
authors.initials: TM
authors.lastname: McCormick
authors.forename: Ashlee A
authors.initials: AA
authors.lastname: Jahnke
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Lough
authors.forename: Dwight S
authors.initials: DS
authors.lastname: Seferos