Energy transfer in oligofluorene-C60 and C60-oligofluorene-C60 donor-acceptor conjugates

被引:31
作者
van der Pol, Cornelia
Bryce, Martin R.
Wielopolski, Mateusz
Atienza-Castellanos, Carmen
Guldi, Dirk M.
Filippone, Salvatore
Martin, Nazario
机构
[1] Univ Erlangen Nurnberg, Inst Phys Chem, D-91058 Erlangen, Germany
[2] Univ Durham, Dept Chem, Durham DH1 3LE, England
[3] Univ Complutense, Fac Ciencias Quim, Dept Quim Organ, E-28040 Madrid, Spain
关键词
D O I
10.1021/jo070686e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two complementary series of C-60-(Fl)(n) and C-60-(Fl)(n)-C-60 (Fl = 9,9-dihexylfluorene-2,7-diyl; n = 1-5) derivatives with terminal N-methylfulleropyrrolidine units have been synthesized from CHO-(Fl)(n) and CHO-(Fl)(n)-CHO precursors via 1,3-dipolar cycloaddition reaction of in situ generated azomethine ylides with an excess of C-60. In solution electrochemical experiments, these conjugates give rise to amphoteric redox behavior. Three consecutive quasireversible reduction waves have been observed at the expected potentials for the N-methylfulleropyrrolidine cores. For the C-60-(Fl)(n)-C-60 series, each reduction wave is a two-electron process with no observable interaction between the C-60 units. Two or, in some cases, three oxidation wavesmost of them irreversibleare ascribed to the oligofluorene system. These waves are cathodically shifted with an increasing number of fluorene units and anodically shifted by the conjugated terminal aldehyde units, compared to the N-methylfulleropyrrolidine termini. Steady-state and time-resolved photolytic techniques show that an efficient transduction of singlet excited-state energy transfer prevails from the photoexcited oligofluorene to the energy accepting fullerene.
引用
收藏
页码:6662 / 6671
页数:10
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