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Issue 10, 2017, Issue in Progress
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Ozonolysis of polycyclic aromatic hydrocarbons in participating solvents

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Abstract

Seven polycyclic aromatic hydrocarbon (PAH) compounds that can be considered small models for graphene edges have been treated with ozone in solution. The presence of participating solvents such as water or methanol had a pronounced influence on conversion and identity of the functional groups formed, whereas the regioselectivity of the ozonation remained unaffected. Six previously unreported compounds have been isolated from the ozonolysis of pyrene 1, perylene 2 and benzo[e]pyrene 4. Comparison of the experimental data with calculated local ionization energy surfaces (IES) shows a good correlation, and indicates that this computational tool would be useful to predict the regioselectivity of ozone also for larger PAHs, including graphene and graphene nanoribbons.

Graphical abstract: Ozonolysis of polycyclic aromatic hydrocarbons in participating solvents

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Supplementary files

Article information


Submitted
03 Nov 2016
Accepted
23 Nov 2016
First published
18 Jan 2017

This article is Open Access

RSC Adv., 2017,7, 6152-6159
Article type
Paper

Ozonolysis of polycyclic aromatic hydrocarbons in participating solvents

A. Lundstedt, M. J. Webb and H. Grennberg, RSC Adv., 2017, 7, 6152
DOI: 10.1039/C6RA26248A

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