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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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Details

Original languageEnglish
Pages (from-to)1108-1124
Number of pages17
JournalJournal of Porphyrins and Phthalocyanines
Volume18
Issue number12
DOIs
Publication statusPublished - Dec 2014
Publication typeA1 Journal article-refereed

Abstract

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.

Keywords

  • 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

Publication forum classification

Field of science, Statistics Finland