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One step conversion of 1,5-bis(dimethylamino)naphthalene to salts of “back to back” bis-acridine derivatives

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Abstract

Oxidation of 1,5-bis(dimethylamino)naphthalene with iodine leads directly to a bis(dimethyliminium) derivative of acridino[2,1,9,8-klmna]acridine, containing six fused six-membered rings, as a bis triiodide salt. The cation has a twisted structure due to the minimisation of peri interactions between each dimethyliminium group and a hydrogen atom. Use of TCNQ as oxidizing agent leads to the same dication as a tetrakis(TCNQ) salt, while use of TCNQ-F4 gave a related monocation which is dimethylated on a ring nitrogen atom.

Graphical abstract: One step conversion of 1,5-bis(dimethylamino)naphthalene to salts of “back to back” bis-acridine derivatives

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Article information


Submitted
12 Feb 2020
Accepted
25 Mar 2020
First published
07 Apr 2020

New J. Chem., 2020, Advance Article
Article type
Paper

One step conversion of 1,5-bis(dimethylamino)naphthalene to salts of “back to back” bis-acridine derivatives

S. Yang, J. C. Bristow, M. A. Addicoat and J. D. Wallis, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ00757A

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