Synthesis and Molecular Properties of Two Isomeric Dialkylated Tetrathienonaphthalenes

Abstract

Isomeric 2,8-distannyl 5,11-didodecyl alpha/beta-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl alpha beta-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in alpha beta-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 alpha beta-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-alpha beta-PTTNTT and 5,11-alpha beta-PTTNTT copolymers. 2,8-alpha beta-PTTNTT with the alpha-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 X 10(-2) cm(2) V-1 s(-1).