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Fullerene Derivatives Substituted with Differently Branched Phenyleneethynylene Dendrons: Synthesis, Electronic and Excited State Properties
Author(s) -
Clifford John N.,
Gégout Aline,
Zhang Sheng,
Pereira de Freitas Rossimiriam,
Urbani Maxence,
Holler Michel,
Ceroni Paola,
Nierengarten JeanFrançois,
Armaroli Nicola
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700689
Subject(s) - chemistry , dendrimer , branching (polymer chemistry) , fullerene , excited state , absorption spectroscopy , photochemistry , acceptor , absorption (acoustics) , electrochemistry , polymer chemistry , organic chemistry , electrode , physics , quantum mechanics , nuclear physics , acoustics , condensed matter physics
Fullerene derivatives functionalized with isomeric phenyleneethynylene‐based dendrons possessing either 1,3,5‐triethynylbenzene or 1,2,4‐triethynylbenzene branching units have been prepared. The electrochemical properties of these compounds are not strongly dependent on the branching patterns since the corresponding redox processes are localized either on the C 60 cage (acceptor unit) or on the dialkyloxybenzene moieties (donor units) at the dendron periphery. The photophysical investigations performed in CH 2 Cl 2 have revealed an ultrafast dendron → C 60 energy transfer in all these hybrid systems. Importantly, the different π‐conjugation patterns in the two series have a dramatic effect on their electronic properties as attested by the differences observed in their absorption and emission spectra. The lower lying absorption onset and the wider spectral profile of the dyads with 1,2,4‐triethynylbenzene branching units when compared to their 1,3,5‐triethynylbenzene analogues clearly points out an improved light harvesting capability. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)