Synthesis and Molecular Properties of Two Isomeric Dialkylated Tetrathienonaphthalenes

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• 作者：Shao-Ling Chang ; Chih-Wen Lu ; Yu-Ying Lai ; Jhih-Yang Hsu ; Yen-Ju Cheng
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：368-371
• 全文大小：353K
• ISSN：1523-7052

文摘

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.