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

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N,N-氟硼配合物(BODIPY)染料（Ⅱ、Ⅳ）。其结构和光学性能经核磁、高分辨质谱、单晶、紫外可见吸收光谱、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（液体和固体荧光），其中BODIPYⅣ的液固荧光量子产率分别高达66.0%和76.3%，其固体荧光量子产率较meso位无取代Ⅱ（14.6%）提高了4.2倍。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，亦丰富了双效有机发光材料的种类。

Abstract:

Meso-unsubstituted and methyl group substituted BODIPYs and their ligands have been obtained with indole derivatives and 1, 8-naphthalenimide by condensation and coordination reactions. Structures were characterized by NMR, HRMS, single crystal and electronic spectra. The results indicated that the solid emission spectra red-shifted 34 nm by the introduction of methyl group at meso-position. BODIPYs show high intensity fluorescence in dual state (solution and solid state). The liquid and solid fluorescence quantum yields of Ⅳ are as high as 66% and 76.3% respectively. Its solid fluorescence quantum yield is 4.2 times higher than that of Ⅱ (14.6%). The excellent optical properties of Ⅳ can be attributed to the absence of C—H…π interaction and different “head to tail” π-π stacking between layers. Excellent dual state emission luminogens glowing at red region have been obtained by the introduction of methyl group, which is different from other strategies and enriches the types of dual state organic luminescent materials.