新型茚并芴-6,12-二酮衍生物的合成与性能研究  

Synthesis and Characterization of New Indeno[1,2-b]fluorene-6,12-dione Derivatives

作　　者：王静[1] 吴琳琳 王倩 Wang Jing;Wu Lin-lin;Wang Qian(Department of Chemistry Chemical Engineering,Shangqiu Normal University,Shangqiu,Henan 476000)

机构地区：[1]商丘师范学院化学化工学院,河南商丘476000

出　　处：《有机化学》2023年第1期223-228,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21302120)资助项目。

摘　　要：以2,5-二溴对二甲苯和苯硼酸衍生物为原料,经氧化、酯化、Suzuki偶联、皂化和合环反应,高产率地得到不同烷基链修饰的茚并芴-6,12-二酮衍生物5.在分子中灵活地引入不同长度的烷基链,既提高了分子的溶解性,又可以研究取代基对化合物性质的影响.研究发现新化合物的溶解性和热学、光学稳定性均优于并五苯.化合物5的最低的未占分子轨道(LUMO)能级都低于-3.4 eV,因此具有较高的电子亲和能. 2,8-二异丙基茚并芴-6,12-二酮(5b)和2,8-二正丁基茚并芴-6,12-二酮(5c)具有刚性分子骨架并形成倾斜的面对面层状堆积,层间距分别为0.3457和0.3423 nm,分子层之间较强的π-π相互作用有利于载流子的传输.为有机功能分子的设计提供一定的指导,同时为有机场效应晶体管提供新的材料来源.Indeno fluorene-6,12-dione derivatives 5 modified by different alkyl substitutions were designed and synthesized from 2,5-dibromo-p-xylene and phenylboronic acid derivatives through oxidation, esterification, Suzuki coupling, saponification and cyclization reactions. Alkyl chains of different lengths were introduced into molecules to improve the solubility of the compounds and investigate the effects of systematic substitution variation on their properties. It was found that the solubility, thermal and optical stability of the new compounds were better than those of pentacene. Compounds 5 have increased electronegativities because of the low lowest unoccupied molecular orbital(LUMO) energies(≤-3.4 eV). 2,8-Diisopropylindeno[1,2-b]fluorene-6,12-dione(5b) and 2,8-dibutylindeno[1,2-b]fluorene-6,12-dione(5c) have rigid molecular frameworks and pack into slipped face-to-face π-stacks, the layer spacings are 0.3457 and 0.3423 nm, respectively. The molecular packing could facilitate carrier transport. The properties of these new materials indicate that they are good candidates for applications in organic optoelectronics.

关 键 词：茚并芴 有机半导体材料 SUZUKI偶联反应 单晶结构 刚性骨架 

分 类 号：TQ244.2[化学工程—有机化工]