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

• Published in: Tetrahedron Vol. 70; no. 36; pp. 6222 - 6228
• Main Authors: Durso, Margherita, Zambianchi, Massimo, Zanelli, Alberto, LoBello, M. Grazia, De Angelis, Filippo, Toffanin, Stefano, Cavallini, Susanna, Gentili, Denis, Tinti, Francesca, Cavallini, Massimiliano, Camaioni, Nadia, Melucci, Manuela
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.09.2014; Elsevier
• Subjects: Anthracene; Chemistry; Chemistry, Organic; Direct arylation; Microwave assisted synthesis; Organic materials; Physical Sciences; Science & Technology; Self-assembly; Direct arylation; Anthracene; Self-assembly; Microwave assisted synthesis; Organic materials; HIGH-PERFORMANCE; POLYMERS; MOBILITY; CRYSTAL-STRUCTURE; ORGANIC SEMICONDUCTORS; FIELD-EFFECT TRANSISTORS; OLIGOMERS; 9,10-DIPHENYLANTHRACENE; (HETERO)ARENES; CATALYZED DIRECT ARYLATION
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2014.03.010

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. [Display omitted]