Monoisomeric phthalocyanine-fullerene dyads with e- and cis-3 addition pattern; synthesis, modeling, photovoltage and solar cell experiments

Jenni Ranta, Mika Niskanen, Kimmo Kaunisto, Venla Manninen, M. Elizabeth Mundy, Kirsi Virkki, Hanna Hakola, Terttu I. Hukka, Helge Lemmetyinen

    Tutkimustuotos: ArtikkeliScientificvertaisarvioitu

    2 Sitaatiot (Scopus)

    Abstrakti

    Synthesis and characterization of two A(2)B(2)-type monoisomeric phthalocyanines and phthalocyanine-fullerene (Pc-C-60) dyads, in which fullerene is regioselectively attached to phthalocyanine with two linkers, are described. H-1 NMR spectroscopy results clearly indicate an e addition pattern of the fullerene moiety in trans-dyad 9, and apparently a cis-3 addition pattern in cis-dyad 10. The possible spatial arrangements of 9 and 10 were further examined by molecular modeling. The dyads have polar (-OH) side chains on the fullerene side of the dyad providing a possibility to produce oriented donor-acceptor (D-A) Langmuir monolayers on aqueous subphase, which can be shifted onto a solid surface. When deposited on a solid electrode material, parallel vertical alignment of the phthalocyanine and fullerene moieties in 100% dyad monolayer was obtained and vertical electron transfer from Pc to C 60 upon photoexcitation was demonstrated. Introduction of the dyads as an oriented interfacial monolayer between the photoactive layer and metal anode improved the power conversion efficiency in inverted organic solar cells.

    AlkuperäiskieliEnglanti
    Sivut1108-1124
    Sivumäärä17
    JulkaisuJournal of Porphyrins and Phthalocyanines
    Vuosikerta18
    Numero12
    DOI - pysyväislinkit
    TilaJulkaistu - jouluk. 2014
    OKM-julkaisutyyppiA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

    Julkaisufoorumi-taso

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