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A Supramolecular [10]CPP Junction Enables Efficient Electron Transfer in Modular Porphyrin–[10]CPP⊃Fullerene Complexes
Author(s) -
Xu Youzhi,
Wang Bingzhe,
Kaur Ramandeep,
Minameyer Martin B.,
Bothe Michael,
Drewello Thomas,
Guldi Dirk M.,
von Delius Max
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201802443
Subject(s) - porphyrin , fullerene , supramolecular chemistry , photoinduced electron transfer , moiety , chemistry , electron transfer , photochemistry , intramolecular force , acceptor , electron acceptor , molecule , stereochemistry , organic chemistry , physics , condensed matter physics
Efficient photoinduced electron transfer was observed across a [10]cycloparaphenylene ([10]CPP) moiety that serves as a rigid non‐covalent bridge between a zinc porphyrin and a range of fullerenes. The preparation of iodo‐[10]CPP is the key to the synthesis of a porphyrin–[10]CPP conjugate, which binds C 60 , C 70 , (C 60 ) 2 , and other fullerenes ( K A >10 5 m −1 ). Fluorescence and pump–probe spectroscopy revealed intramolecular energy transfer between CPP and porphyrin and also efficient charge separation between porphyrin and fullerenes, affording up to 0.5 μs lifetime charge‐separated states. The advantage of this approach towards electron donor–acceptor dyads is evident in the case of dumbbell‐shaped (C 60 ) 2 , which gave intricate charge‐transfer behavior in 1:1 and 2:1 complexes. These results suggest that [10]CPP and its cross‐coupled derivatives could act as supramolecular mediators of charge transport in organic electronic devices.