红光区双效发光材料BODIPY的制备及其光谱性质  

Preparation and photophysical properties of red region dual-state emission BODIPY

作　　者：粟鹏 袁晓慧 晏佳莹 郑开波 王龙 张诺诺 SU Peng;YUAN Xiaohui;YAN Jiaying;ZHENG Kaibo;WANG Long;ZHANG Nuonuo(Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials,College of Materials and Chemical Engineering,China Three Gorges University,Yichang 443002,Hubei,China;Hubei Three Gorges Laboratory,Yichang 443007,Hubei,China;Hubei Yimeite Holographic Technology Co.,Ltd.,Yichang 443100,Hubei,China)

机构地区：[1]三峡大学材料与化工学院湖北省无机非金属晶态与能源转换材料重点实验室,湖北宜昌443002 [2]湖北三峡实验室,湖北宜昌443007 [3]湖北宜美特全息科技有限公司,湖北宜昌443100

出　　处：《精细化工》2023年第6期1272-1279,共8页Fine Chemicals

基　　金：国家自然科学基金(22108157);国家级111引智基地(D20015)。

摘　　要：通过吲哚衍生物与1,8-萘内酰亚胺缩合及氟硼化反应,得到meso位无取代和甲基取代的两种配体(Ⅰ、Ⅲ)及两种氟硼二吡咯(BODIPY)染料(Ⅱ、Ⅳ)。其结构和光学性能经NMR、HRMS、单晶、UV-Vis吸收光谱、荧光发射光谱和固体荧光光谱进行了表征。结果表明,meso位引入甲基后配体Ⅲ较配体Ⅰ的固体荧光发射峰红移了34 nm。BODIPY染料具有较强的双效荧光(溶液和固体荧光),其中BODIPY染料Ⅳ的溶液和固体荧光量子产率分别高达65.8%和76.3%,其固体荧光量子产率较meso位无取代BODIPY染料Ⅱ(14.6%)提高了4.2倍。BODIPY染料Ⅳ较强的双效发光可归因于其固体堆积方式中无C—H…π作用以及层与层之间存在的“头-尾”π-π堆积。不同于其他提高固态荧光的策略,在母体meso位引入小位阻甲基的策略使BODIPY具有双效红光发射性能,也丰富了双效有机发光材料的种类。Two meso-unsubstituted ligands(Ⅰ,Ⅲ)and two methyl group substituted N,N-fluoroborate complex(BODIPY)dyes(Ⅱ,Ⅳ)were synthesized from condensation and coordination reactions of indole derivatives and 1,8-naphthalenimide.The structures and spectral properties of products obtained were characterized by NMR,HRMS,single crystal,UV-Vis absorption spectrum,fluorescence emission spectrum and solid fluorescence spectrum.The results indicated that the introduction of methyl group at meso-position made the solid emission spectra of ligandⅢred-shift 34 nm compared with that of ligandⅠ.BODIPY dyes displayed high intensity fluorescence in dual state(solution state and solid state),especially,the corresponding fluorescence quantum yields ofⅣwere as high as 65.8%and 76.3%,with solid fluorescence quantum yield 4.2 times higher than that ofⅡ(14.6%).The excellent optical properties ofⅣcould be attributed to the absence of C—H…πinteraction and different"head to tail"π-πstacking between layers.Different from other strategies in solid-state fluorescence improvement,the strategy of introducing small steric methyl group in the parent meso site made BODIPY exhibit dual-effect red light emission performance,and enriched the types of dual-effect organic luminescent materials as well.

关 键 词：红光发光 双效荧光 氟硼配合物 高效固态荧光 有机发光材料 功能材料 

分 类 号：O641.4[理学—物理化学] TB34[理学—化学]