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

doi:10.1142/S1088424614500928

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

Research output: Contribution to journal › Article › Scientific › peer-review

2 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1108-1124
Number of pages	17
Journal	Journal of Porphyrins and Phthalocyanines
Volume	18
Issue number	12
DOIs	https://doi.org/10.1142/S1088424614500928
Publication status	Published - Dec 2014
Publication type	A1 Journal article-refereed

Funding

Funding from the Academy of Finland has enabled the computational work, which is greatly appreciated. Computing resources provided by the CSC-IT Center for Science Ltd, administrated by the Finnish Ministry of Education, are acknowledged. We thank Dr. Alexander Efimov for mass spectrometry measurements.

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

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10.1142/S1088424614500928

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Ranta, J., Niskanen, M., Kaunisto, K., Manninen, V., Mundy, M. E., Virkki, K., Hakola, H., Hukka, T. I., & Lemmetyinen, H. (2014). Monoisomeric phthalocyanine-fullerene dyads with e- and cis-3 addition pattern; synthesis, modeling, photovoltage and solar cell experiments. Journal of Porphyrins and Phthalocyanines, 18(12), 1108-1124. https://doi.org/10.1142/S1088424614500928

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

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",

author = "Jenni Ranta and Mika Niskanen and Kimmo Kaunisto and Venla Manninen and Mundy, {M. Elizabeth} and Kirsi Virkki and Hanna Hakola and Hukka, {Terttu I.} and Helge Lemmetyinen",

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Ranta, J, Niskanen, M, Kaunisto, K, Manninen, V, Mundy, ME, Virkki, K, Hakola, H, Hukka, TI & Lemmetyinen, H 2014, 'Monoisomeric phthalocyanine-fullerene dyads with e- and cis-3 addition pattern; synthesis, modeling, photovoltage and solar cell experiments', Journal of Porphyrins and Phthalocyanines, vol. 18, no. 12, pp. 1108-1124. https://doi.org/10.1142/S1088424614500928

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T1 - Monoisomeric phthalocyanine-fullerene dyads with e- and cis-3 addition pattern; synthesis, modeling, photovoltage and solar cell experiments

AU - Ranta, Jenni

AU - Niskanen, Mika

AU - Kaunisto, Kimmo

AU - Manninen, Venla

AU - Mundy, M. Elizabeth

AU - Virkki, Kirsi

AU - Hakola, Hanna

AU - Hukka, Terttu I.

AU - Lemmetyinen, Helge

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PY - 2014/12

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N2 - 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.

AB - 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.

KW - phthalocyanine

KW - phthalocyanine-fullerene dyad

KW - photovoltage

KW - molecular modeling

KW - solar cell

KW - Langmuir-Schafer

KW - PHOTOINDUCED ELECTRON-TRANSFER

KW - MOLECULAR-FORCE FIELD

KW - PORPHYRIN-FULLERENE

KW - CHARGE SEPARATION

KW - DENSITY

KW - MMFF94

KW - C-60

KW - BISADDUCTS

KW - ISOMERS

KW - FILMS

U2 - 10.1142/S1088424614500928

DO - 10.1142/S1088424614500928

M3 - Article

SN - 1088-4246

VL - 18

SP - 1108

EP - 1124

JO - Journal of Porphyrins and Phthalocyanines

JF - Journal of Porphyrins and Phthalocyanines

IS - 12

ER -

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

Abstract

Funding

Keywords

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