Reported herein is the first example of a transition-metal-catalyzed internal oxidative C-H/C-H cross-coupling between two (hetero)arenes through a traceless oxidation directing strategy. Without the requirement of an external metal oxidant, a wide range of phenols, including phenol-containing natural products, can undergo the coupling with azoles to assemble a large library of highly functionalized 2-(2-hydroxyphenyl)azoles. The route provides an opportunity to rapidly screen white-light-emitting materials. As illustrative examples, two bis(triphenylamine)-bearing 2-(2-hydroxyphenyl)oxazoles, which are difficult to access otherwise, exhibit bright white-light emission, high quantum yield, and thermal stability. Also presented is the first example of the white-light emission, in a single excited-state intramolecular proton transfer system, of 2-(2-hydroxyphenyl)azoles, thus highlighting the charm of C-H activation in the discovery of new organic optoelectronic materials.
Considerable efforts have been devoted to the development of highly efficient blue light‐emitting materials. However, deep‐blue fluorescence materials that can satisfy the Commission Internationale de l'Eclairage (CIE) coordinates of (0.14, 0.08) of the National Television System Committee (NTSC) standard blue and, moreover, possess a high external quantum efficiency (EQE) over 5%, remain scarce. Here, the unusual luminescence properties of triphenylamine‐bearing 2‐(2′‐hydroxyphenyl)oxazoles (3a–3c) and their applications in organic light‐emitting diodes (OLEDs) are reported as highly efficient deep‐blue emitters. The 3a‐based device exhibits a high spectral stability and an excellent color purity with a narrow full‐width at half‐maximum of 53 nm and the CIE coordinates of (0.15, 0.08), which is very close to the NTSC standard blue. The exciton utilization of the device closes to 100%, exceeding the theoretical limit of 25% in conventional fluorescent OLEDs. Experimental data and theoretical calculations demonstrate that 3a possesses a highly hybridized local and charge‐transfer excited state character. In OLEDs, 3a exhibits a maximum luminance of 9054 cd m−2 and an EQE up to 7.1%, which is the first example of highly efficient blue OLEDs based on the sole enol‐form emission of 2‐(2′‐hydroxyphenyl)azoles.
The Cu-catalysed oxidative C-H/C-H coupling reaction of azoles has been used for the first time to develop polymerisation, which provides an efficient method for the preparation of polybenzodiimidazoles. These polymers exhibit high molecular weights, regioregularity, blue-emitting performance and thermal stability.
Reported herein is the first example of a direct arylation of heteroarenes by a transient-ligand-directed strategy without the need to construct and deconstruct the directing group. A wide range of heteroarenes undergoes the coupling with diverse aryl iodides to assemble a large library of highly selective and functionalized 3-arylthiophene-2-carbaldehydes. This route provides an opportunity to rapidly access new mechanofluorochromic materials. Moreover, a novel strategy for mechanochromic luminogens with chromism trends of red- and blue-shifts has been disclosed for the first time by facile functional-group modifications to a common structural core.
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