Synthesis of dithieno [3,2-b:2',3'-d] thiophene derivatives from 1,8 diketones

ORGN 556

Olcay Mert, molcay@metu.edu.tr1, Ayhan S. Demir, asdemir@metu.edu.tr1, Turan Ozturk, ozturktur@itu.edu.tr2, and Serap Eroksuz, seraperoksuz@gmail.com1. (1) Department of Chemistry, Middle East Technical University, Inonu Bulvari, Ankara, 06531, Turkey, (2) Department of Chemistry, Istanbul Technical University, Istanbul, 34469
Dithieno[3,2-b:2',3'-d]thiophenes (DTT) are important building blocks of wide variety of materials for electronic and optical applications such as electro-luminescence, two-photon absorption, excited fluorescence, photochromism, and non-linear optical chromophores. Recently, we have developed a new and concise method to synthesize derivatives of DTT, having functional groups at 3- and 5- positions, which are available for further functionalisations. This method opens up a way to form dithienothiophenes via one-pot, dual ring closure reaction of α-dithioketones at 3- and 4- positions of thiophene ring with P4S10 or Lawesson's Reagent. Here we describe one-pot synthesis of dithieno [3,2-b:2',3'-d] thiophene derivatives starting from 1,8 diketones.