Issue 47, 2014

Solid-state photoreactivity of 9-substituted acridizinium bromide salts

Abstract

A series of 9-X-acridizinium bromide salts (where X = F, Cl, Br, I, CH3, C(CH3)3) was synthesised, and their solid-state [4 + 4] photoreactivity was investigated using crystallographic and spectroscopic methods, while their thermal stability was studied using thermal gravimetry and differential-scanning calorimetry. The study aimed to identify how the nature and size of the substituent on the acridizinium cation affected the regioselectivity of the [4 + 4] cycloaddition reactions, the reaction yields and relative reaction rates. Computational methods were utilised to rationalize the unexpectedly high regioselectivity of the solid-state photodimerisation of the 9-Cl-acridizinium bromide salt.

Graphical abstract: Solid-state photoreactivity of 9-substituted acridizinium bromide salts

Supplementary files

Article information

Article type
Paper
Submitted
05 Aug 2014
Accepted
15 Oct 2014
First published
15 Oct 2014
This article is Open Access
Creative Commons BY license

CrystEngComm, 2014,16, 10830-10836

Author version available

Solid-state photoreactivity of 9-substituted acridizinium bromide salts

S. A. Stratford, M. Arhangelskis, D. Bučar and W. Jones, CrystEngComm, 2014, 16, 10830 DOI: 10.1039/C4CE01622J

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