Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119991, Russia.
Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31, Moscow 119071, Russia.
Molecules. 2023 Jan 4;28(2):512. doi: 10.3390/molecules28020512.
Synthetic approach to fluorescent polyaza- and polyoxadiazamacrocycles comprising a structural fragment of 6,7-diamino-2,3-diphenylquinoxaline has been elaborated using Pd-catalyzed amination providing target compounds in yields up to 77%. A series of nine novel - and ,-containing macrocyclic ligands differing by the number of donor sites and cavity size has been obtained. These compounds possess well-pronounced fluorescent properties with emission maxima in a blue region in aprotic solvents and high quantum yields of fluorescence, while in proton media, fluorescence shifts towards the green region of the spectrum. Using macrocycles and as examples, we have shown that such compounds can serve as dual-channel (colorimetric and fluorimetric) pH indicators in water media, with pH transition point and response being dependent on the macrocycle structure due to different sequences of protonation steps.
已用钯催化胺化作用详细阐述了包含 6,7-二氨基-2,3-二苯基喹喔啉结构片段的荧光多氮杂和多氧杂大环的合成方法，提供了高达 77%收率的目标化合物。已经获得了一系列含有九个新型 - 和 - 的大环配体，这些配体的供体位点和腔的大小不同。这些化合物在非质子溶剂中具有良好的荧光性质，发射峰在蓝色区域，荧光量子产率高，而在质子介质中，荧光向光谱的绿色区域移动。以大环 和 为例，我们已经表明，这些化合物可以在水介质中作为双通道（比色和荧光）pH 指示剂，由于质子化步骤的不同顺序，pH 转变点和响应取决于大环的结构。
