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

Yang, S., Bristow, J.C., Addicoat, M.A. ORCID: 0000-0002-5406-7927 and Wallis, J.D. ORCID: 0000-0001-7259-8783, 2020. One step conversion of 1,5-bis(dimethylamino)naphthalene to salts of “back to back” bis-acridine derivatives. New Journal of Chemistry, 44 (23), pp. 9621-9625. ISSN 1144-0546

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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.

Item Type: Journal article
Publication Title: New Journal of Chemistry
Creators: Yang, S., Bristow, J.C., Addicoat, M.A. and Wallis, J.D.
Publisher: Royal Society of Chemistry (RSC)
Date: 21 June 2020
Volume: 44
Number: 23
ISSN: 1144-0546
Identifiers:
NumberType
10.1039/d0nj00757aDOI
1317579Other
Divisions: Schools > School of Science and Technology
Record created by: Jill Tomkinson
Date Added: 17 Jun 2020 12:31
Last Modified: 17 Jun 2020 12:31
URI: http://irep.ntu.ac.uk/id/eprint/40023

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