Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones

Autor: Ching-Chun Tseng, Cheng-Yen Chung, Shuo-En Tsai, Hiroyuki Takayama, Naoto Uramaru, Chin-Yu Lin, Fung Fuh Wong
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Molecules, Vol 25, Iss 10, p 2409 (2020)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules25102409
Popis: 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 (Φf) 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 (Φf) study, the value of compound 6j (0.140) with planar structural skeletal was similar to that of standard luminol (1, 0.175).
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