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Synthesis and Molecular Properties of Two Isomeric Dialkylated Tetrathienonaphthalenes

Synthesis and Molecular Properties of Two Isomeric Dialkylated Tetrathienonaphthalenes

Shao-Ling Chang, Chih-Wen Lu, Yu-Ying Lai, Jhih-Yang Hsu, Yen-Ju Cheng

Org Lett. 2016 Feb 5;18(3):368-71.

PMID: 26741029

Abstract:

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) cm(2) V(-1) s(-1).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4805225	5,5′-Dibromo-2,2′-bithiophene		4805-22-5	Price

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