2-(Thienyl)quinoxaline derivatives and their application in Ir(iii) complexes yielding tuneable deep red emitters

Abstract

The synthesis and characterisation of eleven different 2-(thienyl)quinoxaline species that incorporate different points of functionality, including at the thiophene or quinoxaline rings, are described. These species display variable fluorescence properties in the visible region (λ_em = 401–491 nm) depending upon the molecular structures and extent of conjugation. The series of 2-(thienyl)quinoxaline species were then investigated as cyclometalating agents for Ir(III) to yield [Ir(C^N)₂(bipy)]PF₆ (where C^N = the cyclometalated ligand; bipy = 2,2′-bipyridine). Eight complexes were successfully isolated and fully characterised by an array of spectroscopic and analytical techniques. Two Ir(III) examples were structurally characterised in the solid state using single crystal X-ray diffraction; both structures confirmed the proposed formulations and coordination spheres in each case showing that the thiophene coordinates via a Ir–C bond. The photophysical properties of the complexes revealed that each complex is luminescent under ambient conditions with a range of emission wavelengths observed (665–751 nm) indicating that electronic tuning can be achieved via both the thienyl and quinoxaline moieties.