Accessing New DPP‐Based Copolymers by Direct Heteroarylation Polymerization
作者： Jean-Rémi Pouliot , Lauren G. Mercier , Samuel Caron , Mario Leclerc
关键词: Atomic orbital 、 Copolymer 、 Derivative (chemistry) 、 Conformational energy 、 Density functional theory 、 Polymer chemistry 、 Materials science 、 Organic field-effect transistor 、 Polymerization
摘要: A diketopyrrolopyrrole derivative was copolymerized with different electron-withdrawing units [i.e., thieno[3,4-c]pyrrole-4,6-dione (TPD), bis(thieno[3,4-c]pyrrole-4,6-dione) (BTPD), and 3,4-dicyanothiophene (DCT)] using direct heteroarylation polymerization (DHAP) methodology. Alternating copolymers low-lying frontier orbitals suitable for n-type semiconducting behavior were obtained. Under optimized conditions, reactions reproducible high number-average molecular weights (Mn) achieved. Density functional theory (DFT) calculations indicated that the structures lowest conformational energy had planar backbones. Preliminary results showed these new low-bandgap materials exhibit good behavior.
sci-hub.se 参考文章(44)
Hsiang-Yu Chen, Jianhui Hou, Shaoqing Zhang, Yongye Liang, Guanwen Yang, Yang Yang, Luping Yu, Yue Wu, Gang Li, Polymer solar cells with enhanced open-circuit voltage and efficiency Nature Photonics. ,vol. 3, pp. 649- 653 ,(2009) , 10.1038/NPHOTON.2009.192
Serge I. Gorelsky, David Lapointe, Keith Fagnou, Analysis of the palladium-catalyzed (aromatic)C-H bond metalation-deprotonation mechanism spanning the entire spectrum of arenes. Journal of Organic Chemistry. ,vol. 77, pp. 658- 668 ,(2012) , 10.1021/JO202342Q
Philippe Berrouard, Ahmed Najari, Agnieszka Pron, David Gendron, Pierre-Olivier Morin, Jean-Rémi Pouliot, Justine Veilleux, Mario Leclerc, Synthesis of 5-Alkyl[3,4-c]thienopyrrole-4,6-dione-Based Polymers by Direct Heteroarylation Angewandte Chemie International Edition. ,vol. 51, pp. 2068- 2071 ,(2012) , 10.1002/ANIE.201106411
Herman T Nicolai, M Kuik, GAH Wetzelaer, B De Boer, C Campbell, C Risko, JL Brédas, PWM Blom, None, Unification of trap-limited electron transport in semiconducting polymers Nature Materials. ,vol. 11, pp. 882- 887 ,(2012) , 10.1038/NMAT3384
Marie-France Falzon, Arjan P. Zoombelt, Martijn M. Wienk, René A. J. Janssen, Diketopyrrolopyrrole-based acceptor polymers for photovoltaic application Physical Chemistry Chemical Physics. ,vol. 13, pp. 8931- 8939 ,(2011) , 10.1039/C1CP20313D
Ting Lei, Yue Cao, Xu Zhou, Yang Peng, Jiang Bian, Jian Pei, Systematic Investigation of Isoindigo-Based Polymeric Field-Effect Transistors: Design Strategy and Impact of Polymer Symmetry and Backbone Curvature Chemistry of Materials. ,vol. 24, pp. 1762- 1770 ,(2012) , 10.1021/CM300117X
Wei Lu, Junpei Kuwabara, Takaki Kanbara, Polycondensation of Dibromofluorene Analogues with Tetrafluorobenzene via Direct Arylation Macromolecules. ,vol. 44, pp. 1252- 1255 ,(2011) , 10.1021/MA1028517
Ta-Ya Chu, Jianping Lu, Serge Beaupré, Yanguang Zhang, Jean-Rémi Pouliot, Salem Wakim, Jiayun Zhou, Mario Leclerc, Zhao Li, Jianfu Ding, Ye Tao, Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3% Journal of the American Chemical Society. ,vol. 133, pp. 4250- 4253 ,(2011) , 10.1021/JA200314M
Yuning Li, Prashant Sonar, Samarendra P. Singh, Mui Siang Soh, Martin van Meurs, Jozel Tan, Annealing-free high-mobility diketopyrrolopyrrole-quaterthiophene copolymer for solution-processed organic thin film transistors. Journal of the American Chemical Society. ,vol. 133, pp. 2198- 2204 ,(2011) , 10.1021/JA1085996
Sebastian Kowalski, Sybille Allard, Ullrich Scherf, Synthesis of Poly(4,4-dialkyl-cyclopenta[2,1-b:3,4-b′]dithiophene-alt-2,1,3-benzothiadiazole) (PCPDTBT) in a Direct Arylation Scheme ACS Macro Letters. ,vol. 1, pp. 465- 468 ,(2012) , 10.1021/MZ300093W