Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 11, 2014
Previous Article Next Article

A comparative study on the performance of subphthalocyanines and corannulene derivatives as receptors for fullerenes

Author affiliations

Abstract

Herein, we have employed dispersion corrected density functional theory to study the performance of modified subphthalocyanines and dibenzo[a,g]corannulenes as fullerene receptors. Analysis of the interaction energies and structures of the catchers revealed that subphthalocyanines display excellent ball–socket interactions with C60 and C70. However, dibenzo[a,g]corannulene showed an excellent fit only with C70, as indicated by recent experimental results. Functionalization of subphthalocyanines with long thioalkyl chains increases the interaction energies between receptors and fullerenes. Yet, the effect on the association constant is negligible, and in some cases it can be even harmful, because the long alkyl chains introduce large entropic penalties, which are translated into a small improvement of the free energy changes. We propose a new subphthalocyanine based receptor which bears three 1,4-dithino groups at the peripheral region. The new host has a strong affinity towards C60 and C70, as indicated by theoretical calculations, which showed a large change in free energy when the above-mentioned modification is considered. In spite of the fact that long alkyl chains seem not to be useful in improving the binding affinity of several receptors, we have found that the addition of small ethyl chains to dibenzo[a,g]corannulene increases the affinity of the bowl towards fullerenes. Nevertheless, new functional groups must be attached in places where the stacking interaction between the host and the guest is barely affected; otherwise the loss of π stacking should be compensated by the new functional groups.

Graphical abstract: A comparative study on the performance of subphthalocyanines and corannulene derivatives as receptors for fullerenes

Back to tab navigation

Supplementary files

Article information


Submitted
26 May 2014
Accepted
09 Sep 2014
First published
09 Sep 2014

New J. Chem., 2014,38, 5608-5616
Article type
Paper
Author version available

A comparative study on the performance of subphthalocyanines and corannulene derivatives as receptors for fullerenes

P. A. Denis, New J. Chem., 2014, 38, 5608
DOI: 10.1039/C4NJ00865K

Social activity

Search articles by author

Spotlight

Advertisements