Potopnyk Mykhaylo A, Kravets Mykola, Luboradzki Roman, Volyniuk Dmytro, Sashuk Volodymyr, Grazulevicius Juozas Vidas
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Org Biomol Chem. 2021 Jan 21;19(2):406-415. doi: 10.1039/d0ob02225j.
Two highly emissive carbazole-containing thiazole-fused oxadiazaborinines were designed and synthesized. These N,O-chelated organoboron dyes displayed large Stokes shifts and remarkable solvatofluorochromism in solutions, as well as good thermal stability and comparatively high photoluminescence quantum yields (up to 34%) in the solid state. The presence of a carbazole donor unit, linked with the oxadiazaborinine acceptor via a phenyl linker, restricted intramolecular rotation, leading to enhanced aggregation-induced emission properties of the compounds: in THF/water mixtures with a large water percentage, they demonstrated the formation of emissive nanoaggregates with an average size of 79 and 89 nm for complexes 2 and 3, respectively. The introduction of bulky tert-butyl groups attached to the carbazole moiety induced significant mechanofluorochromic properties of the compounds.
设计并合成了两种高发射性的含咔唑噻唑稠合恶二唑硼啉。这些N,O-螯合有机硼染料在溶液中表现出大的斯托克斯位移和显著的溶剂化荧光变色现象，在固态下具有良好的热稳定性和相对较高的光致发光量子产率（高达34%）。通过苯基连接体与恶二唑硼啉受体相连的咔唑供体单元的存在限制了分子内旋转，导致化合物的聚集诱导发光性质增强：在水含量高的四氢呋喃/水混合物中，配合物2和3分别形成了平均尺寸为79和89 nm的发射性纳米聚集体。连接到咔唑部分的庞大叔丁基的引入诱导了化合物显著的机械荧光变色性质。
