1,3,5,7,9-五蒽基心环烯的合成及表征  

Synthesis and characterization of 1,3,5,7,9-pentaanthracenylcorannulene

作　　者：杜军婕 苏茵 陈佐长 张前炎[1] 谢素原[1] DU Junjie;SU Yin;CHEN Zuochang;ZHANG Qianyan;XIE Suyuan(State Key Laboratory of Physical Chemistry of Solid Surfaces,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China)

机构地区：[1]厦门大学化学化工学院,固体表面物理化学国家重点实验室,福建厦门361005

出　　处：《厦门大学学报（自然科学版）》2023年第5期807-814,共8页Journal of Xiamen University：Natural Science

基　　金：国家自然科学基金(91961113);厦门市青年创新基金(3502Z20206054)。

摘　　要：大多数已合成的C_(5)对称的五取代心环烯衍生物的荧光强度偏弱,这在一定程度上限制了其作为光电材料的应用.本研究通过1,3,5,7,9-五硼酯代心环烯与溴化蒽分子之间的五重Suzuki偶联反应,成功实现了具有C_(5)对称结构的1,3,5,7,9-五蒽基心环烯分子的合成.借助高分辨质谱、核磁共振波谱和X射线单晶衍射等手段对其五取代碗状结构进行了精确的表征,并结合紫外-可见吸收光谱、荧光发射光谱和密度泛函理论计算对其分子轨道和光学性质进行了研究.结果表明,合成的1,3,5,7,9-五蒽基心环烯的荧光量子产率达到38.8%,较未经修饰的心环烯增强了近29倍,其合成有望拓展心环烯衍生物在发光材料领域的应用.The fluorescence intensity of most synthesized C_(5)symmetric penta-substituted corannulene derivatives is weak,thereby limiting their application as photoelectric materials.In this study,the synthesis of 1,3,5,7,9-pentaanthracenylcorannulene with C_(5)symmetrical structure was achieved by a five-fold Suzuki coupling reaction between 1,3,5,7,9-pentakis(BPin)corannulene and anthracene bromide.Its bowl-shaped structure was accurately characterized using high-resolution mass spectrometry,nuclear magnetic resonance spectroscopy and X-ray single crystal diffraction.Combined with ultraviolet-visible absorption spectroscopy,fluorescence emission spectroscopy and density functional theory calculations,we examined its molecular orbitals and optical properties.The results showed that the fluorescence quantum yield of 1,3,5,7,9-pentaanthracenylcorannulene is 38.8%,which is nearly 29 times higher than that of unmodified corannulene.The synthesis of 1,3,5,7,9-pentaanthracenylcorannulene has the potential to expand the application of corannulene derivatives in the field of luminescent materials.

关 键 词：心环烯 蒽 1 3 5 7 9-五蒽基心环烯 荧光 

分 类 号：O613.42[理学—无机化学] O613.71[理学—化学]