有机化学ChineseJournalofOrganicChemistryARTICLE*Correspondingauthor.E-mail:wj2150@yeah.netReceivedJune21,2022;revisedJuly26,2022;publishedonlineSeptember1,2022.ProjectsupportedbytheNationalNaturalScienceFoundationofChina(No.21302120).国家自然科学基金(No.21302120)资助项目.Chin.J.Org.Chem.2023,43,223～228©2023ShanghaiInstituteofOrganicChemistry,ChineseAcademyofScienceshttp://sioc-journal.cn/223DOI:10.6023/cjoc202206038研究论文新型茚并芴-6,12-二酮衍生物的合成与性能研究王静*吴琳琳王倩(商丘师范学院化学化工学院河南商丘476000)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－3.4eV,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0.3423nm,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.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SynthesisandCharacterizationofNewIndeno[1,2-b]fluorene-6,12-dioneDerivativesWang,Jing*Wu,LinlinWang,Qian(DepartmentofChemistryChemicalEngineering,ShangqiuNormalUniversity,Shangqiu,Henan476000)AbstractIndenofluorene-6,12-dionederivatives5modifiedbydifferentalkylsubstitutionsweredesignedandsynthesizedfrom2,5-dibromo-p-xyleneandphenylboronicacidderivativesthroughoxidation,esterification,Suzukicoupling,saponi-ficationandcyclizationreactions.Alkylchainsofdifferentlengthswereintroducedintomoleculestoimprovethesolubilityofthecompoundsandinvestigatetheeffectsofsystematicsubstitutionvariationontheirproperties.Itwasfoundthatthesolubility,thermalandopticalstabilityofthenewcompoundswerebetterthanthoseofpentacene.Compounds5havein-creasedelectronegativitiesbecauseofthelowlowestunoccupiedmolecular...
