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Issue 5, 2012
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Immobilizing NIR absorbing azulenocyanines onto single wall carbon nanotubes—from charge transfer to photovoltaics

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Abstract

In this fundamental study, the supramolecular interactions between SWNTs and either symmetrical Zn(II) octa-tert-butylazulenocyanine 1 or a Zn(II) azulenocyanine-phthalocyanine 2 bearing a pyrene unit have been evaluated. The synthetic protocol allowed for the preparation of unsymmetrical azulenocyanine-phthalocyanine molecules, which incorporate reactive hydroxyl functional groups useful for the preparation of more elaborate derivatives, that is, the pyrene containing derivative 2 by an esterification reaction. To shed light onto the mutual interactions between 1 or 2 and SWNT, stable suspensions of SWNT in a mixture of 25% THF and 75% DMF were titrated with variable amounts of 1 or 2. These assays indicate a successful immobilization of azulenocyanine derivatives 1 or 2 onto SWNTs to yield the supramolecular hybrids SWNT/1 and SWNT/2. In this light, the physico-chemical properties of 1 and 2 as well as those of SWNT/1 and SWNT/2 were investigated. From these we conclude strong interactions in the ground state, and a rapid charge separation in the excited state of SWNT/1 or SWNT/2. The accordingly formed radical ion pair states decay with lifetimes of 124 and 137 ps for SWNT/1 and SWNT/2, respectively. Finally, SWNT/1 and SWNT/2 were integrated into photoelectrochemical cells, revealing a response throughout the visible and near-infrared with a moderate IPCE maxima of 2.5%.

Graphical abstract: Immobilizing NIR absorbing azulenocyanines onto single wall carbon nanotubes—from charge transfer to photovoltaics

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Supplementary files

Article information


Submitted
15 Jan 2012
Accepted
22 Feb 2012
First published
24 Feb 2012

Chem. Sci., 2012,3, 1472-1480
Article type
Edge Article

Immobilizing NIR absorbing azulenocyanines onto single wall carbon nanotubes—from charge transfer to photovoltaics

M. Ince, J. Bartelmess, D. Kiessling, K. Dirian, M. V. Martínez-Díaz, T. Torres and D. M. Guldi, Chem. Sci., 2012, 3, 1472
DOI: 10.1039/C2SC20071F

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