Synthesis and characterization of thieno[3,4-b]pyrazine-based terthienyls: tunable precursors for low band gap conjugated materials.

作者: Ryan L. Schwiderski , Seth C. Rasmussen

DOI: 10.1021/JO400577Q

关键词:

摘要: Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5,7-bis(2-thienyl)thieno[3,4-b]pyrazines. From these reactive intermediates, a variety 2,3-difunctionalized 5,7-bis(2-thienyl)thieno[3,4-b]pyrazines produced as precursors to conjugated materials. Structural, electronic, optical characterization analogues illustrate extent which electronic nature functional groups can be used tune properties thieno[3,4-b]pyrazine-based terthienyl units.

参考文章(57)
Seth C. Rasmussen, Michael E. Mulholland, Ryan L. Schwiderski, Cole A. Larsen, Thieno[3,4‐b]pyrazines and Its Extended Analogs: Important Buildings Blocks for Conjugated Materials Journal of Heterocyclic Chemistry. ,vol. 49, pp. 479- 493 ,(2012) , 10.1002/JHET.1051
Hong Mo, Karla R. Radke, Katsu Ogawa, Christopher L. Heth, Brett T. Erpelding, Seth C. Rasmussen, Solution and solid-state properties of highly fluorescent dithieno[3,2-b:2′,3′-d]pyrrole-based oligothiophenes Physical Chemistry Chemical Physics. ,vol. 12, pp. 14585- 14595 ,(2010) , 10.1039/C0CP00970A
Seth C. Rasmussen, Ryan L. Schwiderski, Michael E. Mulholland, Thieno[3,4-b]pyrazines and their applications to low band gap organic materials Chemical Communications. ,vol. 47, pp. 11394- 11410 ,(2011) , 10.1039/C1CC12754C
Payman Tehrani, Joakim Isaksson, Wendimagegn Mammo, Mats R. Andersson, Nathaniel D. Robinson, Magnus Berggren, Evaluation of active materials designed for use in printable electrochromic polymer displays Thin Solid Films. ,vol. 515, pp. 2485- 2492 ,(2006) , 10.1016/J.TSF.2006.07.149
John D. Bradshaw, Don Solooki, Claire A. Tessier, Wiley J. Youngs, LITHIUM-INDUCED CYCLIZATION OF TETRABENZOCYCLYNE. A NOVEL ZIPPER REACTION OF CYCLIC O-ETHYNYLBENZENES Journal of the American Chemical Society. ,vol. 116, pp. 3177- 3179 ,(1994) , 10.1021/JA00087A001
Martin Helgesen, Frederik C. Krebs, Photovoltaic Performance of Polymers Based on Dithienylthienopyrazines Bearing Thermocleavable Benzoate Esters Macromolecules. ,vol. 43, pp. 1253- 1260 ,(2010) , 10.1021/MA9024812
Mehdi Ghandi, Saleh Salahi, Mohammad Hasani, A mild, expedient, one-pot trifluoromethanesulfonic anhydride mediated synthesis of N-arylimidates Tetrahedron Letters. ,vol. 52, pp. 270- 273 ,(2011) , 10.1016/J.TETLET.2010.11.019
Chitoshi Kitamura, Shoji Tanaka, Yoshiro Yamashita, Synthesis of new narrow bandgap polymers based on 5,7-di(2-thienyl)thieno[3,4-b]pyrazine and its derivatives Journal of The Chemical Society, Chemical Communications. pp. 1585- 1586 ,(1994) , 10.1039/C39940001585
Yangjun Xia, Jie Luo, Xianyu Deng, Xianzhen Li, Dongyun Li, Xuhui Zhu, Wei Yang, Yong Cao, None, Novel Random Low-Band-Gap Fluorene-Based Copolymers for Deep Red/Near Infrared Light-Emitting Diodes and Bulk Heterojunction Photovoltaic Cells Macromolecular Chemistry and Physics. ,vol. 207, pp. 511- 520 ,(2006) , 10.1002/MACP.200500517