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Issue 47, 2014
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Solid-state photoreactivity of 9-substituted acridizinium bromide salts

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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

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Supplementary files

Article information


Submitted
05 Aug 2014
Accepted
15 Oct 2014
First published
15 Oct 2014

This article is Open Access

CrystEngComm, 2014,16, 10830-10836
Article type
Paper
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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