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Electronic Communication through π‐Conjugated Wires in Covalently Linked Porphyrin/C 60 Ensembles
Author(s) -
de la Torre Gema,
Giacalone Francesco,
Segura José L.,
Martín Nazario,
Guldi Dirk M.
Publication year - 2005
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.200400604
Subject(s) - porphyrin , conjugated system , molecular wire , electron transfer , tetraphenylporphyrin , materials science , electron acceptor , covalent bond , photochemistry , chemical physics , electron donor , acceptor , chemistry , molecule , polymer , physics , organic chemistry , catalysis , condensed matter physics , composite material
Novel photo‐ and electroactive triads, in which π‐conjugated p ‐phenylenevinylene oligomers (oPPVs) of different length are connected to a photoexcited‐state electron donor (i.e., zinc tetraphenylporphyrin) and an electron acceptor (i.e., C 60 ), were designed, synthesized, and tested as electron‐transfer model systems. A detailed physicochemical investigation, concentrating mainly on long‐range charge separation and charge recombination and kinetics, revealed small attenuation factors β of 0.03±0.005 Å −1 . Energy matching between the HOMO levels of C 60 and oPPVs emerged as a key parameter for supporting molecular‐wire‐like behavior: It favors rapid and efficient electron or hole injection into the oPPV wires. Large electronic coupling values were determined as a result of paraconjugation in the oPPV moieties.
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