含受限吡唑基苝（吡唑并苝）生色团的高荧光染料。
Highly Fluorescent Dyes Containing Conformationally Restrained Pyrazolylpyrene (Pyrazoolympicene) Chromophore.
机构信息
Department of Organic Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland.
Biological and Chemical Research Center, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland.
出版信息
Molecules. 2022 Feb 14;27(4):1272. doi: 10.3390/molecules27041272.
The triflic-acid-promoted cyclization of 1-phenyl-3-(pyren-1-yl)-1-pyrazole-4-carbaldehyde afforded a mixture of 9-phenyl-7,9-dihydropyreno (10,1-)indazole and 9-phenylpyreno(10,1-)indazole-7(9)-one, readily separable by column chromatography. Both products contained a rigid six-ringed pyrazoolympicene backbone and exhibited bright fluorescence in chloroform solution and a weak fluorescence in the solid state. DFT and TD DFT calculations revealed that the lowest excited state (S) of these compounds is populated via HOMO →LUMO π-π * transition. Furthermore, the synthesized compounds behaved as weak bases and their emission spectra showed substantial changes upon protonation. Therefore, they may be of interest for sensing of strongly acidic fluorophore environments.
三氟乙酸促进 1-苯基-3-(芘-1-基)-1-吡唑-4-甲醛的环化反应得到了 9-苯基-7,9-二氢并吡咯并[10,1-]吲唑和 9-苯基并吡咯并[10,1-]吲唑-7(9)-酮的混合物，通过柱色谱法很容易分离。这两种产物都含有刚性的六环吡唑并[10,1-d]吲唑骨架，并在氯仿溶液中表现出明亮的荧光，在固态下则表现出较弱的荧光。DFT 和 TD DFT 计算表明，这些化合物的最低激发态（S）通过 HOMO→LUMO π-π*跃迁来填充。此外，合成的化合物表现为弱碱，其发射光谱在质子化后发生了显著变化。因此，它们可能对强酸性荧光团环境的传感具有重要意义。
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