Issue 12, 2015
From the journal:

Chemical Science

Naphthalenebisimides as photofunctional surfactants for SWCNTs – towards water-soluble electron donor–acceptor hybrids†

Konstantin Dirian,‡a   Susanne Backes,‡a   Claudia Backes,b   Volker Strauss,a   Fabian Rodler,a   Frank Hauke,a   Andreas Hirsch*a  and  Dirk M. Guldi*a  

* Corresponding authors

a Department of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany
E-mail: andreas.hirsch@fau.de, dirk.guldi@fau.de

b School of Physics, Trinity College Dublin, Dublin 2, Ireland

Abstract

A water soluble naphthalenebisimide derivative (NBI) was synthesized and probed to individualize, suspend, and stabilize single wall carbon nanotubes (SWCNTs). Besides a comprehensive photophysical and electrochemical characterization of NBI, stable suspensions of SWCNTs were realized in buffered D2O. Overall, the dispersion efficiency of the NBI surfactant was determined by comparison with naphthalene based references. Successful individualization of SWCNTs was corroborated in several microscopic assays. In addition, emission spectroscopy points to the strong quenching of SWCNT centered band gap emission, when NBIs are immobilized onto SWCNTs. The origin of the quenching was found to be strong electronic communication, which leads to charge separation between NBIs and photoexcited SWCNTs, and, which yields reduced NBIs as well oxidized SWCNTs. Notably, electrochemical considerations revealed that the energy content of these charge separated states is one of the highest reported for SWCNT based electron donor–acceptor hybrids so far.

Graphical abstract: Naphthalenebisimides as photofunctional surfactants for SWCNTs – towards water-soluble electron donor–acceptor hybrids

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Article information

DOI
https://doi.org/10.1039/C5SC02944A
Article type
Edge Article
Submitted
10 Aug 2015
Accepted
22 Sep 2015
First published
22 Sep 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 6886-6895

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Naphthalenebisimides as photofunctional surfactants for SWCNTs – towards water-soluble electron donor–acceptor hybrids

K. Dirian, S. Backes, C. Backes, V. Strauss, F. Rodler, F. Hauke, A. Hirsch and D. M. Guldi, Chem. Sci., 2015, 6, 6886 DOI: 10.1039/C5SC02944A

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