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Open AccessArticle

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

1
The Ph.D. Program for Biotech Pharmaceutical Industry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan
2
School of Pharmacy, China Medical University, No. 91 Hsueh-Shih Rd., Taichung 40402, Taiwan
3
Department of Medico Pharmaceutical Science, Nihon Pharmaceutical University, Komuro Inamachi Kita-adachi-gun, Saitama-ken 10281, Japan
4
Department of Environmental Science, Nihon Pharmaceutical University, Komuro Inamachi Kita-adachi-gun, Saitama-ken 10281, Japan
5
Institute of New Drug Development, College of Biopharmaceutical and Food Sciences, China Medical University, No. 91 Hsueh-Shih Rd., Taichung 40402, Taiwan
*
Author to whom correspondence should be addressed.
Academic Editors: Vera L. M. Silva, Artur M. S. Silva and Elena Cariati
Molecules 2020, 25(10), 2409; https://doi.org/10.3390/molecules25102409
Received: 28 March 2020 / Revised: 19 May 2020 / Accepted: 19 May 2020 / Published: 21 May 2020
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). View Full-Text
Keywords: pyrazolopyridopyridazine dione; N-aminopyrazolopyrrolopyridine dione; luminol; photoluminescence pyrazolopyridopyridazine dione; N-aminopyrazolopyrrolopyridine dione; luminol; photoluminescence
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MDPI and ACS Style

Tseng, C.-C.; Chung, C.-Y.; Tsai, S.-E.; Takayama, H.; Uramaru, N.; Lin, C.-Y.; Wong, F.F. Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones. Molecules 2020, 25, 2409.

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