Synthesis and photophysical properties of a Sc3N@C80 -corrole electron donor-acceptor conjugate.
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 Sc3 N@C80 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 Sc3 N@C80 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.
Key Laboratory of Theoretical Chemistry, Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201 (China).
Bin
B
Liu
Hongyun
H
Fang
Xiaofang
X
Li
Wenting
W
Cai
Lipiao
L
Bao
Marc
M
Rudolf
Fabian
F
Plass
Louzhen
L
Fan
Xing
X
Lu
Dirk M
DM
Guldi
D061565:Cycloaddition Reaction; D004583:Electrons; D037741:Fullerenes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry*
D037741:Fullerenes; D009942:Organometallic Compounds; D011166:Porphyrins; C431863:corrole; D012538:Scandium
corroles; donor-acceptor systems; fullerenes; metallocycles; photophysics