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Programmed Synthesis of Tetraarylthieno[3,2-b]thiophene by Site-Selective Suzuki Cross-Coupling Reactions of Tetrabromothieno[3,2-b]thiophene

In the paper "Programmed Synthesis of Tetraarylthieno[3,2-b]thiophene by Site-Selective Suzuki Cross-Coupling Reactions of Tetrabromothieno[3,2-b]thiophene", Thieno[3,2-b]thiophene is a structural motif that can be found in many important organic materials. A number of mono-, diand tetraarylthieno[3,2-b]thiophenes are reported herein. | LETTER 93 Programmed Synthesis of Tetraarylthieno 3 2-b thiophene by Site-Selective letter Suzuki Cross-Coupling Reactions of Tetrabromothieno 3 2-b thiophene Hien Nguyen a Dung Xuan Nguyen a Thinh Quang Tran a Binh Ngoc Vo a Thao Huong Nguyen a Thi Minh Programmed Synthesis of Tetraarylthieno 3 2-b thiophene Ha Vuong b Tung T. Dang c 1 a Department of Chemistry Hanoi National University of Education 136 Xuanthuy Street Caugiay District Hanoi Vietnam E-mail hiennguyenp@yahoo.com b Laboratoire de Chimie Moléculaire et Thio-organique 6 Boulevard Maréchal Juin 14050 Caen France c Center d elaboration de matériaux et d etudes structurales 29 rue Jeanne Marvig BP 94347 31055 Toulouse Cedex 4 France E-mail dang.thanhtung@gmail.com Received 08.07.2013 Accepted after revision 02.10.2013 Abstract Thieno 3 2-b thiophene is a structural motif that can be S found in many important organic materials. A number of mono- di- and tetraarylthieno 3 2-b thiophenes are reported herein. S S C13H27 Key words cross-coupling reactions palladium Suzuki Miyaura S reaction site selectivity thieno 3 2-b thiophene DNTT C13BTBT C12H25 Thieno 3 2-b thiophene2 is a structural motif present in a S S PBTTT wide range of conducting polymers p-type organic semi- S S conductors optoelectronics nonlinear optics and electro- C12 H25 n luminescence materials. Thieno 3 2-b thiophene can be used as a starting material in the synthesis of oligo-func- Figure 1 Some organic materials containing thieno 3 2-b thiophene tionalized thieno 3 2-b thiophenes thienoacenes and he- lical thienoacenes which are conducting polymers and and tetrabromofuran 8 based on site-selective palladi- chromophores.2b 3 In 2006 McCulloch et al. reported a um 0 -catalyzed Suzuki reactions. liquid-crystalline semiconducting polymer PBTTT con- taining thieno 3 2-b thiophene moieties with a very high Due to the importance of thieno 3 2-b thiophene in mate- charge-carrier mobility Figure 1 .4a Recently dinaph- rials science we were .