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Issue 13, 2020
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Photoactive preorganized subphthalocyanine-based molecular tweezers for selective complexation of fullerenes

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Abstract

The development of new chromophoric receptors capable of binding curved carbon nanostructures is central to the quest for improved fullerene-based organic photovoltaics. We herein report the synthesis and characterization of a subphthalocyanine-based multicomponent ensemble consisting of two electron-rich SubPc-monomers rigidly attached to the convex surface of an electron-poor SubPc-dimer. Such a unique configuration, especially in terms of the two SubPc-monomers, together with the overall stiffness of the linker, endows the multicomponent system with a well-defined tweezer-like topology to efficiently embrace a fullerene in its inner cavity. The formation of a 1 : 1 complex was demonstrated in a variety of titration studies with either C60 or C70. In solution, the underlying association constants were of the order of 105 M−1. Detailed physicochemical experiments revealed a complex scenario of energy- and electron-transfer processes upon photoexcitation in the absence and presence of fullerenes. The close proximity of the fullerenes to the electron-rich SubPcs enables a charge shift from the initially formed reduced SubPc-dimer to either C60 to C70.

Graphical abstract: Photoactive preorganized subphthalocyanine-based molecular tweezers for selective complexation of fullerenes

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Supplementary files

Article information


Submitted
04 Jan 2020
Accepted
27 Feb 2020
First published
28 Feb 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 3448-3459
Article type
Edge Article

Photoactive preorganized subphthalocyanine-based molecular tweezers for selective complexation of fullerenes

G. Zango, M. Krug, S. Krishna, V. Mariñas, T. Clark, M. V. Martinez-Diaz, D. M. Guldi and T. Torres, Chem. Sci., 2020, 11, 3448
DOI: 10.1039/D0SC00059K

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