A Supramolecular [10]CPP Junction Enables Efficient Electron Transfer in Modular Porphyrin-[10]CPP-Fullerene Complexes.

A Supramolecular [10]CPP Junction Enables Efficient Electron Transfer in Modular Porphyrin-[10]CPP-Fullerene Complexes.
Angew Chem Int Ed Engl. 2018 Jul 09;:
Authors: von Delius M, Xu Y, Wang B, Kaur R, Minameyer M, Bothe M, Drewello T, Guldi D
Abstract
[10]Cycloparaphenylene ([10]CPP) has recently been shown to be an excellent supramolecular receptor for C60 and C70. Here we report efficient photoinduced electron transfer across a [10]CPP moiety that serves as a modular, yet rigid, non-covalent bridge between a zinc porphyrin and a diverse range of fullerenes. The first preparation of iodo-[10]CPP is the cornerstone of our synthesis of a porphyrin-[10]CPP conjugate, which was found to bind C60, C70, (C60)2 and other fullerenes with association constants beyond 105 M-1. Fluorescence and pump-probe spectroscopy revealed intramolecular energy transfer between CPP and porphyrin, as well as efficient charge separation between porphyrin and fullerenes, affording up to 0.5 us lived charge-separated states. The advantage of our modular approach towards electron donor-acceptor dyads is particularly evident in the case of dumbbell-shaped (C60)2, which gave rise to intricate charge transfer behaviour in unusual 1:1 and 2:1 complexes. In a broader context, our results suggest that [10]CPP and its cross-coupled derivatives could act as supramolecular mediators of charge transport in organic electronic devices.
PMID: 29985554 [PubMed - as...

Source: Angewandte Chemie - July 9, 2018 Category: Chemistry Authors: von Delius M, Xu Y, Wang B, Kaur R, Minameyer M, Bothe M, Drewello T, Guldi D Tags: Angew Chem Int Ed Engl Source Type: research