Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and <i>N</i>-Aminopyrazolopyrrolopyridine Diones
Ching-Chun Tseng,
Cheng-Yen Chung,
Shuo-En Tsai,
Hiroyuki Takayama,
Naoto Uramaru,
Chin-Yu Lin,
Fung Fuh Wong
Affiliations
Ching-Chun Tseng
The Ph.D. Program for Biotech Pharmaceutical Industry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan
Cheng-Yen Chung
School of Pharmacy, China Medical University, No. 91 Hsueh-Shih Rd., Taichung 40402, Taiwan
Shuo-En Tsai
The Ph.D. Program for Biotech Pharmaceutical Industry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan
Hiroyuki Takayama
Department of Medico Pharmaceutical Science, Nihon Pharmaceutical University, Komuro Inamachi Kita-adachi-gun, Saitama-ken 10281, Japan
Naoto Uramaru
Department of Environmental Science, Nihon Pharmaceutical University, Komuro Inamachi Kita-adachi-gun, Saitama-ken 10281, Japan
Chin-Yu Lin
Institute of New Drug Development, College of Biopharmaceutical and Food Sciences, China Medical University, No. 91 Hsueh-Shih Rd., Taichung 40402, Taiwan
Fung Fuh Wong
The Ph.D. Program for Biotech Pharmaceutical Industry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan
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).
