Abstract
Two subphthalocyanine-C60 conjugates have been prepared by means of the 1,3-dipolar cycloaddition reaction of (perfluoro) or hexa(pentylsulfonyl) electron deficient subphthalocyanines to C60. Comprehensive assays regarding the electronic features – in the ground and excited state – of the resulting conjugates revealed energy and electron transfer processes upon photoexcitation. Most important is the unambiguous evidence – in terms of time-resolved spectroscopy – of an ultrafast oxidative electron transfer evolving from C60 to the photoexcited subphthalocyanines. This is, to the best of our knowledge, the first case of an intramolecular oxidation of C60 within electron donor-acceptor conjugates by means of only photoexcitation.
Highlights
The conversion of solar light into electrical energy remains one of the grand challenges of modern society due to the constantly growing energy demand and resource depletions.[1]
Reports in which fullerenes are employed as electron donors remain, scarce
Examples of conjugates involving SubPcs are limited to only a single case, namely a hexa(octylsulfonyl) SubPc–ferrocene conjugate reported by our group.15d In the present work, and Scheme 1 Synthesis of SubPc–C60 conjugates 1a,b
Summary
The conversion of solar light into electrical energy remains one of the grand challenges of modern society due to the constantly growing energy demand and resource depletions.[1]. Fullerenes – as one of the most explored class of molecular materials – have generated an enormous interest in the eld of nanoelectronics On one hand, their rigid aromatic structure evokes low reorganization energies in electron transfer reactions and, on the other hand, their extended p-conjugation affords efficient charge stabilization.[3] Unique architectural exibility and chemical versatility of fullerenes allow the ne-tuning of their properties by, for example, covalent modi cation of their exterior[4] or incorporation of molecular guests into their interior.[5] In light of the aforementioned, a myriad of electron donor–acceptor conjugates/hybrids have been designed featuring porphyrins,[6] (sub)phthalocyanines,[7,8] perylene-diimides,[9] and other chromophores as light-harvesting electron donors and fullerenes as electron acceptors. Reports in which fullerenes are employed as electron donors remain, scarce
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