Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones
Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones
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DOI：
10.3390/molecules25102409
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发表时间：
2020-05-01
期刊：
影响因子：
4.6
通讯作者：
Wong, Fung Fuh
中科院分区：
文献类型：
--
作者：
Tseng, Ching-Chun;Chung, Cheng-Yen;Wong, Fung Fuh
新设计的吡唑并吡啶并哒嗪二酮和N-氨基吡唑并吡咯并吡啶二酮的鲁米诺结构是由通用的1,3-二芳基呋喃并吡唑并吡啶-6,8-二酮、1,3-二芳基吡唑并吡咯并吡啶-6,8-二酮或1,3-二芳基-7-甲基吡唑并吡咯并吡啶-6,8-二酮合成的，一水合肼。还研究了吡唑并吡啶并哒嗪二酮和 N-氨基吡唑并吡咯并吡啶二酮的光致发光和溶剂化荧光性质，包括 UV-Vis 吸收、发射光谱和量子产率 (Phi (f))。一般来说，与N-氨基吡唑并吡咯并吡啶二酮相比，大多数吡唑并吡咯并吡啶-6,8-二酮6表现出显着的荧光强度和取代基效应，特别是具有间氯基团的6c和6j。此外，由于合适的共轭构象，6j的荧光强度显着增强。根据量子产率 (Phi (f)) 研究，具有平面结构骨架的化合物 6j (0.140) 的值与标准鲁米诺 (1, 0.175) 相似。
The newly designed luminol structures of pyrazolopyridopyridazine diones and N-aminopyrazolopyrrolopyridine diones were synthesized from versatile 1,3-diaryfuropyrazolopyridine-6,8-diones, 1,3-diarylpyrazolopyrrolopyridine-6,8-diones, or 1,3-diaryl-7-methylpyrazolopyrrolopyridine-6,8-diones with hydrazine monohydrate. Photoluminescent and solvatofluorism properties containing UV-Vis absorption, emission spectra, and quantum yield (Phi (f)) study of pyrazolopyridopyridazine diones and N-aminopyrazolopyrrolopyridine diones were also studied. Generally, most of pyrazolopyrrolopyridine-6,8-diones 6 exhibited the significant fluorescence intensity and the substituent effect when compared with N-aminopyrazolopyrrolopyridine diones, particularly for 6c and 6j with a m-chloro group. Additionally, the fluorescence intensity of 6j was significantly promoted due to the suitable conjugation conformation. Based on the quantum yield (Phi (f)) study, the value of compound 6j (0.140) with planar structural skeletal was similar to that of standard luminol (1, 0.175).