Synthesis and molecular properties of two isomeric dialkylated tetrathienonaphthalenes

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

*Corresponding author for this work

Research output: Contribution to journalArticle

8 Scopus citations

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 PtCl 2 -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 .

Original languageEnglish
Pages (from-to)368-371
Number of pages4
JournalOrganic Letters
Volume18
Issue number3
DOIs
StatePublished - 5 Feb 2016

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