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Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation
Author(s) -
Rotas Georgios,
MartínGomis Luis,
Ohkubo Kei,
FernándezLázaro Fernando,
Fukuzumi Shunichi,
Tagmatarchis Nikos,
SastreSantos Ángela
Publication year - 2016
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.201603065
Subject(s) - triad (sociology) , photochemistry , chemistry , acceptor , ultrafast laser spectroscopy , electron donor , photoexcitation , moiety , phthalocyanine , photoinduced electron transfer , electron acceptor , spectroscopy , electron transfer , excited state , stereochemistry , catalysis , organic chemistry , psychology , physics , quantum mechanics , nuclear physics , psychoanalysis , condensed matter physics
The synthesis of a donor–acceptor silicon phthalocyanine (SiPc)‐azafullerene (C 59 N) dyad 1 and of the first acceptor–donor–acceptor C 59 N‐SiPc‐C 59 N dumbbell triad 2 was accomplished. The two C 59 N‐based materials were comprehensively characterized with the aid of NMR spectroscopy, MALDI‐MS as well as DFT calculations and their redox and photophysical properties were evaluated with CV and steady‐state and time‐resolved absorption and photoluminescence spectroscopy measurements. Notably, femtosecond transient absorption spectroscopy assays revealed that both dyad 1 and triad 2 undergo, after selective photoexcitation of the SiPc moiety, photoinduced electron transfer from the singlet excited state of the SiPc moiety to the azafullerene counterpart to produce the charge‐separated state, with lifetimes of 660 ps, in the case of dyad 1 , and 810 ps, in the case of triad 2 . The current results are expected to have significant implications en route to the design of advanced C 59 N‐based donor–acceptor systems targeting energy conversion applications.