发光学报2025，Vol.46Issue(5)：905-911,7.DOI:10.37188/CJL.20240325
基于螺-9,9'-氧杂蒽芴碳基螺环化合物的简易合成、结构及其光电性质
Simple Synthesis of Spiro[fluorene-9,9'-xanthene]-based Carbonyl Spiro-annulation Compound,Structure and Its Photoelectric Properties
摘要
Abstract
Benzoyl chloride and spiro-9,9'-xanthene were used as starting materials,and anhydrous AlCl3 was em-ployed as a catalyst.Then,the compound 2'-(benzoyl)-spiro-9,9'-xanthene(SFXBz)was synthesized facilely by Friedel-Crafts reaction.The crystal structure of SFXBz revealed that the three-dimensional spatial structure of spiro-cyclic carbonyl compound could suppress the intermolecular interactions effectively.It exhibited a high thermal de-composition temperature(Td)of 314℃,which was significantly higher than that of spiro[fluorene-9,9'-xanthene(SFX,Td,258℃)and phenyl sulfone-functionalized SFX(PSSFX,2'-(phenylsulfonyl)spiro[fluorene-9,9'-xan-thene],Td:222℃),indicating that the introduction of a rigid benzoyl moiety could improve the thermal stability of SFX effectively.The differential scanning calorimetry(DSC)curve of SFXBz showed that there was no phase transi-tion when the temperature increased from 40℃ to 220℃ with a high melting point of 202℃.Both of the thermogravi-metric analysis(TGA)and DSC results of SFXBz indicated that the compound had high thermal stability and stable morphology.The density functional theory(DFT)calculations showed that the highest molecular orbital(HOMO)and the lowest unoccupied molecular orbital(LUMO)of SFXBz were separated completely,with energy levels of-5.82 eV and-1.58 eV,respectively.The spatially separated HOMO and LUMO orbitals of SFXBz indicated the compound owned bipolar characteristics.The HOMO and LUMO energy levels of SFXBz were further measured by cy-clic voltammetry,the values of which were-6.22 eV and-1.97 eV,respectively.The deep HOMO energy level of SFXBz was favorable for blocking hole injection and transportion.The UV-absorption and photoluminescence spectrum of the compound showed that the main absorption peaks were at 229 nm,273 nm,299 nm,309 nm,and 348 nm,re-spectively,and its maximum fluorescence emission peak was around 374 nm.The triplet energy level(2.55 eV)of the compound was obtained from the low-temperature phosphorescence spectroscopy,which was higher than those of the classic red and green guest materials(2,4-pentanedionato)bis[2-(2-quinolinyl)phenyl]iridium(Ⅲ)(Ir(pq)2acac,T1,2.10)and fac-Tris[2-phenylpyridinato-C2,N]iridium(Ⅲ)(Ir(PPy)3,T1,2.40 eV),respectively.This indi-cated that the compound could be used as a host material for red and green phosphorescent devices.关键词
螺-9,9'-氧杂蒽芴/简易合成/羰基化合物Key words
spiro[fluorene-9/9'-xanthene]/facile synthesis/carbonyl compound分类
物理学引用本文复制引用
赵祥华,孙青春,孟楚茵,张静伊,解令海,邹国栋,王双双..基于螺-9,9'-氧杂蒽芴碳基螺环化合物的简易合成、结构及其光电性质[J].发光学报,2025,46(5):905-911,7.基金项目
国家自然科学基金(61405170) （61405170）
信阳师范学院"南湖学者奖励计划"青年项目 （）
信阳师范学院大学生科研基金 Supported by National Natural Science Foundation of China(61405170) （61405170）
The Nanhu Scholars Program for Young Scholars of Xinyang Normal University （）
Students Sustentation Fund of Xinyang Normal University （）
