Tellura(benzo)bithiophenes: Synthesis, Oligomerization, and Phosphorescence

Abstract

A series of planar π-extended Te-containing heteroacenes, termed tellura(benzo)bithiophenes, were synthesized. This new structural class of heterocycle features a tellurophene ring fused to a benzobithiophene unit with aromatic side groups (either −C₆H₄ⁱPr or −C₆H₄OCH₃) positioned at the 2- and 5-positions of the tellurophene moiety. Although attempts to enhance molecular rigidity and extend ring-framework π-delocalization in a cumenyl (−C₆H₄ⁱPr)-capped tellura(benzo)bithiophene led to oxidation (and Te–C bond scission) to form a diene–one, the formation of an oligomeric tellura(benzo)bithiophene was possible via Kumada catalyst-transfer polycondensation (KCTP). Furthermore, one tellura(benzo)bithiophene derivative exhibits orange-red phosphorescence at room temperature in air when incorporated into a poly(methyl methacrylate) host; accompanying TD-DFT computations provided insight into a potential mechanism for the observed phosphorescence.