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Synthesis, crystal structure, and application of an acenaphtho[1,2- k ] fluoranthene diimide derivative
Science China Chemistry ( IF 9.6 ) Pub Date : 2015-01-04 , DOI: 10.1007/s11426-014-5282-9
Lin Ding , Chiyuan Yang , Zhongmin Su , Jian Pei

Organic electron acceptor materials play an important role in organic electronics. Recently, many organic electron acceptors have been developed, in which aromatic fused-imides have proved to be a promising family of excellent electron acceptors. We report the first synthesis of a novel aromatic fused-imide, acenaphtho[1, 2- k ]fluoranthene diimide derivative ( AFI ), using lithium-halogen exchange and Diels-Alder reactions. The construction of a large conjugated plane and the introduction of electron-withdrawing imide groups endow AFI with a low lowest unoccupied molecular orbital (LUMO) level of −3.80 eV. AFI exhibits a regular molecular arrangement and strong π-π interactions in the single-crystal structure, which indicates its potential application in organic electronic devices. Solar cell devices that were fabricated using AFI as the electron acceptor and P3HT as the electron donor achieved an energy conversion efficiency of 0.33%.

中文翻译:

ena [1,2- k ]荧蒽二酰亚胺衍生物的合成,晶体结构及应用

有机电子受体材料在有机电子学中起重要作用。近来,已经开发了许多有机电子受体,其中芳族熔融酰亚胺已被证明是有希望的优良电子受体家族。我们报告了使用锂-卤素交换和Diels-Alder反应的新型芳族稠合酰亚胺,[1,2- k ]荧蒽二酰亚胺衍生物( AFI )的首次合成 。大共轭平面的构建和吸电子酰亚胺基团的引入使 AFI 的最低最低未占据分子轨道(LUMO)水平为-3.80 eV。 AFI 在单晶结构中表现出规则的分子排列和强大的π-π相互作用,这表明其在有机电子器件中的潜在应用。使用 AFI 作为电子受体并使用P3HT作为电子供体制造的太阳能电池器件 实现了0.33%的能量转换效率。
更新日期:2015-01-04
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