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Assemblies of Boron Dipyrromethene/Porphyrin, Phthalocyanine, and C 60 Moieties as Artificial Models of Photosynthesis: Synthesis, Supramolecular Interactions, and Photophysical Studies
Author(s) -
Chen XiaoFei,
ElKhouly Mohamed E.,
Ohkubo Kei,
Fukuzumi Shunichi,
Ng Dennis K. P.
Publication year - 2018
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.201705843
Subject(s) - bodipy , phthalocyanine , porphyrin , photochemistry , artificial photosynthesis , chemistry , ultrafast laser spectroscopy , excited state , electron transfer , materials science , fluorescence , photocatalysis , spectroscopy , organic chemistry , catalysis , physics , quantum mechanics , nuclear physics
A series of light‐harvesting conjugates based on a zinc(II) phthalocyanine core with either two or four boron dipyrromethene (BODIPY) or porphyrin units have been synthesized and characterized. The conjugation of BODIPY/porphyrin units can extend the absorptions of the phthalocyanine core to cover most of the visible region. Upon addition of an imidazole‐substituted C 60 (C 60 Im), it can axially bind to the zinc(II) center of the phthalocyanine core through metal–ligand interactions. The resulting complexes form photosynthetic antenna‐reaction center mimics in which the BODIPY/porphyrin units serve as the antennas to capture the light and transfer the energy to the phthalocyanine core by efficient excitation energy transfer. The excited phthalocyanine is then quenched by the axially bound C 60 Im moiety by electron transfer, which has been supported by computational studies. The photoinduced processes of the assemblies have been studied in detail by various steady‐state and time‐resolved spectroscopic methods. By femtosecond transient absorption spectroscopic studies, the lifetimes of the charge‐separated state of the bis(BODIPY) and bis(porphyrin) systems have been determined to be 3.2 and 4.0 ns, respectively.