Synthesis by MW-assisted direct arylation, side-arms driven self-assembly and functional properties of 9,10-dithienylanthracene orthogonal materials

We report a new class of multifunctional 9,10-dithienylanthracene-based materials having an anthracene π-core functionalized at the 9,10 positions with thienyl side-arms of different size and type of substitution. MW-assisted double direct arylation reaction is employed for the first time to synthesize the target molecules in one-step, organometallic free conditions, in only 5 min and yields up to 80% rather than by a multi-step Stille coupling taken as conventional reference approach. DFT calculations reveal a molecular conformation characterized by the thienyl rings orthogonal to the anthracene core. Nevertheless, despite the non-coplanar structure, all compounds exhibited highly crystalline cast films emitting blue light, with an extraordinary variability in morphology and hole mobility up to 8×10−3 cm2 V−1 s−1.

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