Laboratory of Physical Organic Chemistry, Latvian Institute of Organic Synthesis, LV-1006 Riga, Latvia.
Department of Applied Chemistry, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, Latvia.
Molecules. 2021 Apr 28;26(9):2570. doi: 10.3390/molecules26092570.
New substituted azomethines of benzanthrone with heterocyclic substituents were synthesized by condensation reaction of 3-aminobenzo[de]anthracen-7-one with appropriate aromatic aldehydes. The resulting imines were reduced with sodium borohydride to the corresponding amines, the luminescence of which is more pronounced in comparison with the initial azomethines. The novel benzanthrone derivatives were characterized by NMR, IR, MS, UV/Vis, and fluorescence spectroscopy. The structure of three dyes was studied by the X-ray single crystal structure analysis. The solvent effect on photophysical behaviors of synthesized imines and amines was investigated. The obtained compounds absorb at 420-525 nm, have relatively large Stokes shifts (up to 150 nm in ethanol), and emit at 500-660 nm. The results testify that emission of the studied compounds is sensitive to the solvent polarity, exhibiting negative fluorosolvatochromism for the synthesized azomethines and positive fluorosolvatochromism for the obtained amines. The results obtained indicate that the synthesized compounds are promising as luminescent dyes.
新的取代苯并[de]蒽酮的取代亚甲胺与杂环取代基是通过 3-氨基苯并[de]蒽-7-酮与适当的芳香醛的缩合反应合成的。所得亚胺用硼氢化钠还原得到相应的胺，其发光强度与初始亚甲胺相比更为明显。这些新型苯并蒽酮衍生物通过 NMR、IR、MS、UV/Vis 和荧光光谱进行了表征。通过 X 射线单晶结构分析研究了三种染料的结构。研究了溶剂对合成亚甲胺和胺的光物理行为的影响。所得化合物在 420-525nm 处吸收，具有较大的斯托克斯位移（在乙醇中可达 150nm），并在 500-660nm 处发射。结果表明，研究化合物的发射对溶剂极性敏感，合成的亚甲胺表现出负氟溶剂化变色，而得到的胺则表现出正氟溶剂化变色。所得结果表明，所合成的化合物有作为发光染料的潜力。
