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Synthesis and Molecular Properties of Two Isomeric Dialkylated Tetrathienonaphthalenes
- Chang, Shao-Ling, Lu, Chih-Wen, Lai, Yu-Ying, Hsu, Jhih-Yang, Cheng, Yen-Ju
- Organic letters 2016 v.18 no.3 pp. 368-371
- chemical reactions, composite polymers, moieties, naphthalene, solubility
- Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl₂-catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures. Compounds 1 and 2 were polymerized with a 5,5′-dibromo-2,2′-bithiophene-based monomer to afford 2,8-αβ-PTTNTT and 5,11-αβ-PTTNTT copolymers. 2,8-αβ-PTTNTT with the α-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 × 10–² cm² V–¹ s–¹.