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

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Original languageEnglish
Pages (from-to)1108-1124
Number of pages17
JournalJournal of Porphyrins and Phthalocyanines
Issue number12
Publication statusPublished - Dec 2014
Publication typeA1 Journal article-refereed


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.


  • phthalocyanine, phthalocyanine-fullerene dyad, photovoltage, molecular modeling, solar cell, Langmuir-Schafer, PHOTOINDUCED ELECTRON-TRANSFER, MOLECULAR-FORCE FIELD, PORPHYRIN-FULLERENE, CHARGE SEPARATION, DENSITY, MMFF94, C-60, BISADDUCTS, ISOMERS, FILMS

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Field of science, Statistics Finland