Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan, People's Republic of China.
J Fluoresc. 2011 Jan;21(1):355-64. doi: 10.1007/s10895-010-0724-z. Epub 2010 Oct 2.
A series of novel 5-aryl-3-ferrocenyl-1-pyridazinyl pyrazoline derivatives was synthesized by the reaction of ferrocenyl chalcone and 3-chloro-6-hydrazinylpyridazine in 10-65% yields. The compounds were characterized using IR, (1)H NMR, HRMS spectroscopic techniques and representative compounds 3c and 4c were assigned based on the X-ray crystallographic structure. The absorption and fluorescence characteristics of the compounds were investigated in chloroform, tetrahydrofuran and acetonitrile, respectively. The results showed that the absorption maxima of the compounds varied from 323 to 327 nm depending on the groups bonded to benzene and pyridazine ring. The maximum emission spectra of compounds in CHCl(3) were dependent on groups in pyridazine ring in which a strong donating-electron group such as propoxyl group on pyridazine ring in N-1 position of pyrazoline made the emission wavelength of 4a-4e small red shifte than that of compounds 3a-3e with chlorine group. The intensity of absorption and fluorescence was also correlated with substituent on aryl ring in C-5 position of pyrazoline. In addition, the absorption spectra of these compounds changed very little, but the fluorescence spectra had much change with increasing solvent polarity.
通过将二茂铁基查尔酮与 3-氯-6-肼基哒嗪反应，合成了一系列新型 5-芳基-3-二茂铁基-1-哒嗪基吡唑啉衍生物，产率为 10-65%。使用红外、（1）H NMR、高分辨率质谱光谱技术对化合物进行了表征，并基于 X 射线晶体学结构对代表性化合物 3c 和 4c 进行了分配。研究了化合物在氯仿、四氢呋喃和乙腈中的吸收和荧光特性。结果表明，化合物的吸收最大值取决于与苯环和哒嗪环结合的基团，从 323 到 327nm 不等。在 CHCl（3）中，化合物的最大发射光谱取决于哒嗪环上的基团，其中哒嗪环上 N-1 位的丙氧基等强供电子基团使 4a-4e 的发射波长比带有氯基团的化合物 3a-3e 小红移。吸收和荧光的强度也与吡唑啉 C-5 位芳基环上的取代基有关。此外，这些化合物的吸收光谱变化很小，但荧光光谱随溶剂极性的增加有很大变化。
