Photovoltaic and electrocatalytic properties of novel ball-type phthalocyanines bridged with four dicumarol

Ümit Salan; Ahmet Altindal; Ali Riza Özkaya; Bekir Salih; Özer Bekaroǧlu

doi:10.1039/c2dt12510b

Photovoltaic and electrocatalytic properties of novel ball-type phthalocyanines bridged with four dicumarol

Ümit Salan^*, Ahmet Altindal, Ali Riza Özkaya, Bekir Salih, Özer Bekaroǧlu

^*Corresponding author for this work

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

33 Citations (Scopus)

Abstract

The new ball-type metallo bisphthalocyanines (Co ₂Pc ₂ and Zn ₂Pc ₂) were synthesized from the corresponding [4,4′-bis(dicoumaroylphthalonitrile)] which can be obtained from the reaction of 3,3′-methylenebis(4-hydroxy-2H-chromen-2-one) and 4-nitrophthalonitrile. The structures of the newly synthesized compounds have been confirmed and characterized by elemental analysis, UV/Vis, IR and ¹H NMR spectroscopies and MALDI-TOF mass spectrometry. Solar cells of the configuration ITO/Co ₂Pc ₂/C60/Al and ITO/Zn ₂Pc ₂/C60/Al were fabricated. The effect of the thickness of the active Pc layer - the thickness of the Pc layer was varied from 15 to 80 nm - on solar cells parameters has been investigated. A nearly thickness independent open circuit voltage was observed in both structures. The maximum photovoltaic conversion efficiency, short circuit current and fill factor were observed in ITO/Zn ₂Pc ₂/C60/Al cell with 80 nm Pc layer to be 0.255%, 1 mA cm ^-2 and 0.38, respectively. The redox properties of the ball-type complexes were investigated by cyclic voltammetry, controlled-potential coulometry and in situ spectroelectrochemistry in DMSO-TBAP. The electrochemical measurements showed that the complexes form ring-based and/or metal-based mixed-valence species, due to the remarkable intramolecular interactions between the two metal phthalocyanine units. The Vulcan XC-72(VC)/Nafion(Nf)/Co ₂Pc ₂ modified glassy carbon electrode showed much higher catalytic performance towards oxygen reduction, compared to the VC/Nf/Zn ₂Pc ₂ modified one. It was found that the VC/Nf/Co ₂Pc ₂ catalyst is nearly insensitive to the presence of methanol. In the presence of 1 M methanol in the electrolyte, the catalytic performance of the Co ₂Pc ₂-based catalyst in oxygen reduction was much better than that of the Pt-based one. Thus, it was shown that the VC/Nf/Co ₂Pc ₂ catalyst can be a good alternative to VC/Nf/Pt as a cathode catalyst in direct methanol fuel cells.

Original language	English
Pages (from-to)	5177-5187
Number of pages	11
Journal	Dalton Transactions
Volume	41
Issue number	17
DOIs	https://doi.org/10.1039/c2dt12510b
Publication status	Published - 7 May 2012
Externally published	Yes

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10.1039/c2dt12510b

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@article{613b3892a24343ae9549279ee5349b10,

title = "Photovoltaic and electrocatalytic properties of novel ball-type phthalocyanines bridged with four dicumarol",

abstract = "The new ball-type metallo bisphthalocyanines (Co 2Pc 2 and Zn 2Pc 2) were synthesized from the corresponding [4,4′-bis(dicoumaroylphthalonitrile)] which can be obtained from the reaction of 3,3′-methylenebis(4-hydroxy-2H-chromen-2-one) and 4-nitrophthalonitrile. The structures of the newly synthesized compounds have been confirmed and characterized by elemental analysis, UV/Vis, IR and 1H NMR spectroscopies and MALDI-TOF mass spectrometry. Solar cells of the configuration ITO/Co 2Pc 2/C60/Al and ITO/Zn 2Pc 2/C60/Al were fabricated. The effect of the thickness of the active Pc layer - the thickness of the Pc layer was varied from 15 to 80 nm - on solar cells parameters has been investigated. A nearly thickness independent open circuit voltage was observed in both structures. The maximum photovoltaic conversion efficiency, short circuit current and fill factor were observed in ITO/Zn 2Pc 2/C60/Al cell with 80 nm Pc layer to be 0.255%, 1 mA cm -2 and 0.38, respectively. The redox properties of the ball-type complexes were investigated by cyclic voltammetry, controlled-potential coulometry and in situ spectroelectrochemistry in DMSO-TBAP. The electrochemical measurements showed that the complexes form ring-based and/or metal-based mixed-valence species, due to the remarkable intramolecular interactions between the two metal phthalocyanine units. The Vulcan XC-72(VC)/Nafion(Nf)/Co 2Pc 2 modified glassy carbon electrode showed much higher catalytic performance towards oxygen reduction, compared to the VC/Nf/Zn 2Pc 2 modified one. It was found that the VC/Nf/Co 2Pc 2 catalyst is nearly insensitive to the presence of methanol. In the presence of 1 M methanol in the electrolyte, the catalytic performance of the Co 2Pc 2-based catalyst in oxygen reduction was much better than that of the Pt-based one. Thus, it was shown that the VC/Nf/Co 2Pc 2 catalyst can be a good alternative to VC/Nf/Pt as a cathode catalyst in direct methanol fuel cells.",

author = "{\"U}mit Salan and Ahmet Altindal and {\"O}zkaya, {Ali Riza} and Bekir Salih and {\"O}zer Bekaroǧlu",

year = "2012",

month = may,

day = "7",

doi = "10.1039/c2dt12510b",

language = "English",

volume = "41",

pages = "5177--5187",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "17",

}

TY - JOUR

T1 - Photovoltaic and electrocatalytic properties of novel ball-type phthalocyanines bridged with four dicumarol

AU - Salan, Ümit

AU - Altindal, Ahmet

AU - Özkaya, Ali Riza

AU - Salih, Bekir

AU - Bekaroǧlu, Özer

PY - 2012/5/7

Y1 - 2012/5/7

N2 - The new ball-type metallo bisphthalocyanines (Co 2Pc 2 and Zn 2Pc 2) were synthesized from the corresponding [4,4′-bis(dicoumaroylphthalonitrile)] which can be obtained from the reaction of 3,3′-methylenebis(4-hydroxy-2H-chromen-2-one) and 4-nitrophthalonitrile. The structures of the newly synthesized compounds have been confirmed and characterized by elemental analysis, UV/Vis, IR and 1H NMR spectroscopies and MALDI-TOF mass spectrometry. Solar cells of the configuration ITO/Co 2Pc 2/C60/Al and ITO/Zn 2Pc 2/C60/Al were fabricated. The effect of the thickness of the active Pc layer - the thickness of the Pc layer was varied from 15 to 80 nm - on solar cells parameters has been investigated. A nearly thickness independent open circuit voltage was observed in both structures. The maximum photovoltaic conversion efficiency, short circuit current and fill factor were observed in ITO/Zn 2Pc 2/C60/Al cell with 80 nm Pc layer to be 0.255%, 1 mA cm -2 and 0.38, respectively. The redox properties of the ball-type complexes were investigated by cyclic voltammetry, controlled-potential coulometry and in situ spectroelectrochemistry in DMSO-TBAP. The electrochemical measurements showed that the complexes form ring-based and/or metal-based mixed-valence species, due to the remarkable intramolecular interactions between the two metal phthalocyanine units. The Vulcan XC-72(VC)/Nafion(Nf)/Co 2Pc 2 modified glassy carbon electrode showed much higher catalytic performance towards oxygen reduction, compared to the VC/Nf/Zn 2Pc 2 modified one. It was found that the VC/Nf/Co 2Pc 2 catalyst is nearly insensitive to the presence of methanol. In the presence of 1 M methanol in the electrolyte, the catalytic performance of the Co 2Pc 2-based catalyst in oxygen reduction was much better than that of the Pt-based one. Thus, it was shown that the VC/Nf/Co 2Pc 2 catalyst can be a good alternative to VC/Nf/Pt as a cathode catalyst in direct methanol fuel cells.

AB - The new ball-type metallo bisphthalocyanines (Co 2Pc 2 and Zn 2Pc 2) were synthesized from the corresponding [4,4′-bis(dicoumaroylphthalonitrile)] which can be obtained from the reaction of 3,3′-methylenebis(4-hydroxy-2H-chromen-2-one) and 4-nitrophthalonitrile. The structures of the newly synthesized compounds have been confirmed and characterized by elemental analysis, UV/Vis, IR and 1H NMR spectroscopies and MALDI-TOF mass spectrometry. Solar cells of the configuration ITO/Co 2Pc 2/C60/Al and ITO/Zn 2Pc 2/C60/Al were fabricated. The effect of the thickness of the active Pc layer - the thickness of the Pc layer was varied from 15 to 80 nm - on solar cells parameters has been investigated. A nearly thickness independent open circuit voltage was observed in both structures. The maximum photovoltaic conversion efficiency, short circuit current and fill factor were observed in ITO/Zn 2Pc 2/C60/Al cell with 80 nm Pc layer to be 0.255%, 1 mA cm -2 and 0.38, respectively. The redox properties of the ball-type complexes were investigated by cyclic voltammetry, controlled-potential coulometry and in situ spectroelectrochemistry in DMSO-TBAP. The electrochemical measurements showed that the complexes form ring-based and/or metal-based mixed-valence species, due to the remarkable intramolecular interactions between the two metal phthalocyanine units. The Vulcan XC-72(VC)/Nafion(Nf)/Co 2Pc 2 modified glassy carbon electrode showed much higher catalytic performance towards oxygen reduction, compared to the VC/Nf/Zn 2Pc 2 modified one. It was found that the VC/Nf/Co 2Pc 2 catalyst is nearly insensitive to the presence of methanol. In the presence of 1 M methanol in the electrolyte, the catalytic performance of the Co 2Pc 2-based catalyst in oxygen reduction was much better than that of the Pt-based one. Thus, it was shown that the VC/Nf/Co 2Pc 2 catalyst can be a good alternative to VC/Nf/Pt as a cathode catalyst in direct methanol fuel cells.

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U2 - 10.1039/c2dt12510b

DO - 10.1039/c2dt12510b

M3 - Article

AN - SCOPUS:84859787177

SN - 1477-9226

VL - 41

SP - 5177

EP - 5187

JO - Dalton Transactions

JF - Dalton Transactions

IS - 17

ER -

Photovoltaic and electrocatalytic properties of novel ball-type phthalocyanines bridged with four dicumarol

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