J. Technology and Education, Vol.27, No.1, pp.21-25 (2020)

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Development of reduced leuco dye coloring by metal assisted oxidative cleavage

 

Eiki MATSUI*, Kaito TAKASHIMA, Jyunki MAEGAWA, Miku YAMAKOSHI

Department of Chemistry and Biology, National Institute of Technology, Fukui College

(Geshi, Sabae, Fukui 916-8507, Japan)

 

(Received February 28, 2020; Accepted March 23, 2020)

 

Abstract

   Coloring with metal coordination is important in constructing the metal sensors. In this study, We aimed for the synthesis of compounds that lose their protection due to metal coordination and color accordingly. The leuco compound formed by reduction of Methylene Blue is an unstable compound that is easily oxidized and colored. Therefore, we aimed to protect the reduced form of leuco, and convert the reduced form to have metal coordination moiety.

It was possible to protect and stably isolate Leucomethylene Blue 1, and convert to Leucomethylene Blue 2 capable of metal coordination. In the process of converting Leucomethylene Blue 2 into metal coordinated leuco 2, the color of the solution turned dark blue when iron(III) ion was added. By the measurement of ESI-MS, the appearance of metal coordination, elimination of protecting groups, and regenaration of Methylene Blue were confirmed.

Keywords: methylene blue, leuco compound, matal coordination, oxidative cleavage

 

 

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