Synthesis, crystal structure, and application of an acenaphtho[1,2-k] fluoranthene diimide derivative  

作　　者：Lin Ding Chiyuan Yang Zhongmin Su Jian Pei 

机构地区：[1]College of Chemistry and Molecular Engineering, Peking University [2]College of Chemistry, Northeast Normal University

出　　处：《Science China Chemistry》2015年第2期364-369,共6页中国科学（化学英文版）

基　　金：financially supported by the National Basic Research Program of China(2013CB933501);the National Natural Science Foundation of China;supported by a General Financial Grant(2013M530135)from the China Postdoctoral Science Foundation

摘　　要：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 e V.AFI exhibits a regular molecular arrangement and strong - 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%.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%.

关 键 词：acenaphtho fluoranthene diimide lithium-halogen exchange Diels-Alder reaction electron acceptor solar cell 

分 类 号：O625.152[理学—有机化学]