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


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.

SUBMITTER: Zango G 

PROVIDER: S-EPMC8515455 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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

Zango Germán G   Krug Marcel M   Krishna Swathi S   Mariñas Víctor V   Clark Timothy T   Martinez-Diaz M Victoria MV   Guldi Dirk M DM   Torres Tomás T  

Chemical science 20200228 13


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 stif  ...[more]

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