Document Type : Short Communication


1 Faculty of Science and Engineering, Macquarie University, North Ryde, NSW 2109, Australia

2 Department of Biomedical Engineering, University of Minnesota, Minneapolis, MN 55455, USA

3 Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA


Optimized desublimation of 2,4-diaminotoluene (4-methylbenzene-1,3-diamine) formed its ultrapure crystals. The collected crystals were analyzed by X-ray crystallography and then directly consumed in a condensation reaction with paraformaldehyde that resulted in the formation of Hünlich’s base. The subsequent one-pot diazotization and coupling reactions produced a new bisazo analog of Tröger’s base in the maximum possible compliance with the principles of green chemistry. The obtained bisazo product was found to be a durable and affordable building block suitable for use in the design of light-driven molecular machines.

Graphical Abstract

A green one-pot shortcut to light switching Tröger base analogs


Main Subjects

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