Controllable Monobromination of Perylene Ring System: Synthesis of Bay-Functionalized Perylene Dyes

Masaki Takahashi; Kyohei Asaba; Trinh Thi Lua; Toshiyasu Inuzuka; Naohiro Uemura; Masami Sakamoto; Tetsuya Sengoku; Hidemi Yoda

doi:10.1021/acs.joc.7b02540

Controllable Monobromination of Perylene Ring System: Synthesis of Bay-Functionalized Perylene Dyes

J Org Chem. 2018 Jan 19;83(2):624-631. doi: 10.1021/acs.joc.7b02540. Epub 2018 Jan 9.

Authors

Masaki Takahashi¹, Kyohei Asaba¹, Trinh Thi Lua¹, Toshiyasu Inuzuka², Naohiro Uemura³, Masami Sakamoto³, Tetsuya Sengoku¹, Hidemi Yoda¹

Affiliations

¹ Department of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
² Division of Instrumental Analysis, Life Science Research Center, Gifu University , 1-1 Yanagido, Gifu 501-1193, Japan.
³ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University , 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

PMID: 29286661
DOI: 10.1021/acs.joc.7b02540

Abstract

Practical synthesis of bay-monofunctionalized perylene dyes has been developed based on controllable NBS bromination of tetrabenzyl perylene-3,4,9,10-tetracarboxylate. The ability to perform the convenient and high-yielding synthesis highlights the potential utility of our multifunctional approach to access a diverse range of new perylene systems.

Publication types

Research Support, Non-U.S. Gov't