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Synthesis and Photophysical Properties of a Sc 3 N@C 80 ‐Corrole Electron Donor–Acceptor Conjugate
Author(s) -
Liu Bin,
Fang Hongyun,
Li Xiaofang,
Cai Wenting,
Bao Lipiao,
Rudolf Marc,
Plass Fabian,
Fan Louzhen,
Lu Xing,
Guldi Dirk M.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405572
Subject(s) - corrole , photochemistry , photoexcitation , chemistry , electron acceptor , acceptor , excited state , electron transfer , electron donor , moiety , absorption spectroscopy , ultrafast laser spectroscopy , spectroscopy , stereochemistry , atomic physics , organic chemistry , physics , condensed matter physics , catalysis , quantum mechanics
Embedding endohdedral metallofullerenes (EMFs) into electron donor–acceptor systems is still a challenging task owing to their limited quantities and their still largely unexplored chemical properties. In this study, we have performed a 1,3‐dipolar cycloaddition reaction of a corrole‐based precursor with Sc 3 N@C 80 to regioselectively form a [5,6]‐adduct ( 1 ). The successful attachment of the corrole moiety was confirmed by mass spectrometry. In the electronic ground state, absorption spectra suggest sizeable electronic communications between the electron acceptor and the electron donor. Moreover, the addition pattern occurring at a [5,6]‐bond junction is firmly proven by NMR spectroscopy and electrochemical investigations performed with 1 . In the electronically excited state, which is probed in photophysical assays with 1 , a fast electron‐transfer yields the radical ion pair state consisting of the one‐electron‐reduced Sc 3 N@C 80 and of the one‐electron‐oxidized corrole upon its exclusive photoexcitation. As such, our results shed new light on the practical work utilizing EMFs as building blocks in photovoltaics.