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

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 betwe...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2020-06, Vol.44 (23), p.9621-9625
Main Authors: Yang, Songjie, Bristow, Jonathan C, Addicoat, Matthew A, Wallis, John D
Format: Article
Language:English
Subjects:
Crystallography
Iodine
Naphthalene
Oxidation
Oxidizing agents
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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-F 4 gave a related monocation which is dimethylated on a ring nitrogen atom. 1,5-Bis(dimethylamino)naphthalene can be oxidized directly to a dication or a cation derived from an acridino-acridine, the former stabilised by two dimethyliminium substituents, while the latter has a dimethylated nitrogen in the ring system.
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj00757a