3,6-Dithiophen-2-yl-diketopyrrolo[3,2-b]pyrrole (isoDPPT) as an Acceptor Building Block for Organic Opto-Electronics
| Autor: | Hakan Usta, Yan Yao, Yuning Li, Shaofeng Lu, Jingqi Wang, Damien Boudinet, Antonio Facchetti, Hualong Pan, Martin Drees, He Yan |
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| Rok vydání: | 2013 |
| Předmět: |
chemistry.chemical_classification
Materials science Polymers and Plastics Organic Chemistry Electronic structure Electron acceptor Photochemistry Acceptor Inorganic Chemistry chemistry.chemical_compound Crystallography chemistry Materials Chemistry Copolymer Molecular orbital Single crystal HOMO/LUMO Pyrrole |
| Zdroj: | Macromolecules. 46:3895-3906 |
| ISSN: | 1520-5835 0024-9297 |
| DOI: | 10.1021/ma400568b |
| Popis: | The electron acceptor building block for π-conjugated copolymers, 3,6-dithiophen-2-yl-diketopyrrolo[3,2-b]pyrrole (isoDPPT), was synthesized following two routes. The comparison between isoDPPT and widely investigated 3,6-dithiophen-2-yl-diketopyrrolo[3,4-c]pyrrole (DPPT) in terms of molecular orbital computations, single crystal X-ray diffraction, optical absorption and cyclic voltammogram was utilized to elucidate structural and electronic structure differences between the two cores. Both units are found to be planar in the solid state, exhibit similar LUMO energy, however, isoDPPT exhibits a much deeper HOMO energy. Six isoDPPT-based polymers with optical bandgaps spanning from 1.44 to 1.76 eV were synthesized by copolymerizing isoDPPT with the following building blocks: 2,2′-bithiophene (for P1), 4,4′-bis(2-ethylhexyl)-dithieno[3,2-b:2′,3′-d]silole (for P2), 3,3‴-didodecylquaterthiophene (for P3), 4,8-didodecylbenzo[1,2-b:4,5-b′]dithiophene (for P4), 4,8-didodecyloxybenzo[1,2-b:4,5-b′]dithiophene (for... |
| Databáze: | OpenAIRE |
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