发光学报, 2019, 40 (4): 476, 网络出版: 2019-06-10
一种苯磺酰基/螺-9,9′-氧杂蒽芴双极性分子的简易合成法:分子结构与光电性质
A Facile Method to Synthesis of Phenylsulfonyl/Spiro[fluorene-9,9′-xanthene] Bipolar Molecule: Molecular Structure, Optical and Electrochemical Properties
摘要
利用一种简易合成法制备了2′-苯磺酰基-螺-9,9′-氧杂蒽芴(PSSFX)。热重分析曲线和差热扫描曲线表明该化合物在222 ℃时失重5%,加热到160 ℃没有玻璃化转变温度,其熔点为124 ℃。通过磷光光谱计算得到该化合物的三线态能级T1为2.77 eV。利用密度泛函计算得知其 HOMO(-5.83 eV) 和 LUMO(-1.62 eV)轨道相分离。通过循环伏安法得到其HOMO、LUMO和 Eg 分别为-6.33,-2.34, 3.94 eV。这表明缺电子的苯磺酰基有利于改善其电子注入/传输性能。PSSFX在二氯甲烷溶液和晶体粉末的紫外吸收峰分别位于267 nm和274/351 nm左右,发射峰分别位于408 nm和341 nm左右。
Abstract
In this work, a facile method was used to prepare 2′-(phenylsulfonyl)spiro[fluorene-9,9′-xanthene] (PSSFX). The thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) curves demonstrate that PSSFX losed 5% weight at decomposition transition temperature of 222 ℃ and melted at 124 ℃ with no crystallization phenomena by heating to 160 ℃. The high triplet energy level(T1, 2.77 eV) of the compound was calculated from phosphorescence spectrum. The separated the highest occupied molecular orbital (HOMO, -5.83 eV) and the lowest unoccupied molecular orbital (LUMO, -1.62 eV) of the compound were calculated by density functional theory(DFT). Cyclic voltammetry measurements were employed in experiment to obtain the HOMO, LUMO, and Eg of -6.33, -2.34, 3.94 eV, respectively. The optical properties of PSSFX were researched in dichloromethane and crystal powder with absorption peaks around 267, 274/351 nm, and emission peaks at about 408, 341 nm, respectively.
赵祥华, 王莉敏, 王竞园, 唐林, 凌海峰, 许文娟, 陈明, 邹国栋. 一种苯磺酰基/螺-9,9′-氧杂蒽芴双极性分子的简易合成法:分子结构与光电性质[J]. 发光学报, 2019, 40(4): 476. ZHAO Xiang-hua, WANG Li-min, WANG Jing-yuan, TANG Lin, LING Hai-feng, XU Wen-juan, CHEN Ming, ZOU Guo-dong. A Facile Method to Synthesis of Phenylsulfonyl/Spiro[fluorene-9,9′-xanthene] Bipolar Molecule: Molecular Structure, Optical and Electrochemical Properties[J]. Chinese Journal of Luminescence, 2019, 40(4): 476.