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Paper | Regular issue | Vol 91, No. 8, 2015, pp.1585-1590
Published online, 6th July, 2015
DOI: 10.3987/COM-15-13197
NIR-Fluorescent Ethyl 4,7-Bis(5-arylthiophen-2-yl)-1,2,5-oxadiazolo[3,4-c]pyridine-6-carboxylate

Kentaro Nishi,* Nobuyuki Seto, Wataru Iwasaki, Yohei Matsuoka, Yuki Kashiwa, Youichi Sano, Tadashi Kawaharada, Takashi Yazumi, Keiji Mizuki, and Shin-ichiro Isobe

*Faculty of Engineering, Kyushu Sangyo University , 3-1 Matsukadai, 2-Chome, Higashiku, Fukuoka 813-8503, Japan


Ethyl 4,7-bis(5-bromothiophen-2-yl)-1,2,5-oxadiazolo[3,4-c]pyridine-6-carboxylate 2 reacted with phenyl-, 4-methylphenyl-, 4-methoxyphenyl-, 3,4-dimethoxyphenyl-, 1-naphthyl-, and 2-naphthyl-boronic acid to give the corresponding π-extended 4,7-bis(5-arylthiophen-2-yl) derivatives 3a–f, which emitted fluorescence at around 700 nm in DMSO solution. The 4-methoxy and 2-naphthyl derivatives (3c and 3f) emitted fluorescence at 729 nm (13717 cm-1, Φ = 0.02) and 714 nm (14005 cm-1 and Φ = 0.11), respectively, with a large Stokes shift (184 and 182 nm for 3c; 4631 cm-1 and 4791 cm-1 for 3f).