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Aromatic Fluorine-Induced One-Pot Synthesis of Ring-Perfluorinated Trimethine Cyanine Dye and Its Remarkable Fluorescence Properties

Kazumasa Funabiki, Yuki Saito, Takashi Kikuchi, Kazutaka Yagi, Yasuhiro Kubota, Toshiyasu Inuzuka, Yohei Miwa, Michiyuki Yoshida, Osamu Sakurada, Shoichi Kutsumizu

J Org Chem. 2019 Apr 5;84(7):4372-4380.

PMID: 30887808

Abstract:

We have developed a novel aromatic fluorine-induced one-pot synthesis of ring-perfluorinated trimethine cyanine dye without the use of a pyridine by reacting hexafluorobenzoindolenine with 5 equiv of methyl trifluoromethanesulfonate in mixed solvents of dimethylformamide and toluene. The thus-obtained ring-perfluorinated trimethine cyanine dye shows much better fluorescence properties, including intensity, quantum yield, and lifetime, than the nonfluorinated dye, not only in CH2Cl2 solution and the poly(methyl methacrylate) film but also in the powder state. Furthermore, ring-perfluorinated trimethine cyanine dye 2a shows better photostability toward white light-emitting diode irradiation than nonfluorinated dye trimethine cyanine dye 2b.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP333277 Methyl trifluoromethanesulfonate Methyl trifluoromethanesulfonate 333-27-7 Price
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