Syntheses, charge separation, and inverted bulk heterojunction solar cell application of phenothiazine-fullerene dyads

Gwendolyn D. Blanco, Arto J. Hiltunen, Gary N. Lim, Chandra B. KC, Kimmo M. Kaunisto, Tommi Vuorinen, Vladimir N. Nesterov, Helge J. Lemmetyinen, Francis D'Souza

Research output: Contribution to journalArticleScientificpeer-review

23 Citations (Scopus)

Abstract

A series of phenothiazine-fulleropyrrolidine (PTZ-C60) dyads having fullerene either at the C-3 aromatic ring position or at the N-position of phenothiazine macrocycle were newly synthesized and characterized. Photoinduced electron transfer leading to PTZ ?+-C60 ?- charge-separated species was established from studies involving femtosecond transient absorption spectroscopy. Because of the close proximity of the donor and acceptor entities, the C-3 ring substituted PTZ-C60 dyads revealed faster charge separation and charge recombination processes than that observed in the dyad functionalized through the N-position. Next, inverted organic bulk heterojunction (BHJ) solar cells were constructed using the dyads in place of traditionally used [6,6]-phenyl-C61- butyric acid methyl ester (PCBM) and an additional electron donor material poly(3-hexylthiophene) (P3HT). The performance of the C-3 ring substituted PTZ-C60 dyad having a polyethylene glycol substituent produced a power conversion efficiency of 3.5% under inverted bulk heterojunction (BHJ) configuration. This was attributed to optimal BHJ morphology between the polymer and the dyad, which was further promoted by the efficient intramolecular charge separation and relatively slow charge recombination promoted by the dyad within the BHJ structure. The present finding demonstrate PTZ-C60 dyads as being good prospective materials for building organic photovoltaic devices.
Original languageEnglish
Pages (from-to)8481-8490
JournalACS Applied Materials & Interfaces
Volume8
Issue number13
DOIs
Publication statusPublished - 2016
MoE publication typeA1 Journal article-refereed

Fingerprint

Fullerenes
Heterojunctions
Solar cells
Butyric acid
Electrons
Absorption spectroscopy
Polyethylene glycols
Conversion efficiency
Esters
Polymers
phenothiazine

Keywords

  • fullerene
  • phenothiazine
  • photoinduced electron transfer
  • femtosecond transient spectroscopy
  • inverted bulk heterojunction
  • organic photovoltaics

Cite this

Blanco, Gwendolyn D. ; Hiltunen, Arto J. ; Lim, Gary N. ; KC, Chandra B. ; Kaunisto, Kimmo M. ; Vuorinen, Tommi ; Nesterov, Vladimir N. ; Lemmetyinen, Helge J. ; D'Souza, Francis. / Syntheses, charge separation, and inverted bulk heterojunction solar cell application of phenothiazine-fullerene dyads. In: ACS Applied Materials & Interfaces. 2016 ; Vol. 8, No. 13. pp. 8481-8490.
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abstract = "A series of phenothiazine-fulleropyrrolidine (PTZ-C60) dyads having fullerene either at the C-3 aromatic ring position or at the N-position of phenothiazine macrocycle were newly synthesized and characterized. Photoinduced electron transfer leading to PTZ ?+-C60 ?- charge-separated species was established from studies involving femtosecond transient absorption spectroscopy. Because of the close proximity of the donor and acceptor entities, the C-3 ring substituted PTZ-C60 dyads revealed faster charge separation and charge recombination processes than that observed in the dyad functionalized through the N-position. Next, inverted organic bulk heterojunction (BHJ) solar cells were constructed using the dyads in place of traditionally used [6,6]-phenyl-C61- butyric acid methyl ester (PCBM) and an additional electron donor material poly(3-hexylthiophene) (P3HT). The performance of the C-3 ring substituted PTZ-C60 dyad having a polyethylene glycol substituent produced a power conversion efficiency of 3.5{\%} under inverted bulk heterojunction (BHJ) configuration. This was attributed to optimal BHJ morphology between the polymer and the dyad, which was further promoted by the efficient intramolecular charge separation and relatively slow charge recombination promoted by the dyad within the BHJ structure. The present finding demonstrate PTZ-C60 dyads as being good prospective materials for building organic photovoltaic devices.",
keywords = "fullerene, phenothiazine, photoinduced electron transfer, femtosecond transient spectroscopy, inverted bulk heterojunction, organic photovoltaics",
author = "Blanco, {Gwendolyn D.} and Hiltunen, {Arto J.} and Lim, {Gary N.} and KC, {Chandra B.} and Kaunisto, {Kimmo M.} and Tommi Vuorinen and Nesterov, {Vladimir N.} and Lemmetyinen, {Helge J.} and Francis D'Souza",
year = "2016",
doi = "10.1021/acsami.6b00561",
language = "English",
volume = "8",
pages = "8481--8490",
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Blanco, GD, Hiltunen, AJ, Lim, GN, KC, CB, Kaunisto, KM, Vuorinen, T, Nesterov, VN, Lemmetyinen, HJ & D'Souza, F 2016, 'Syntheses, charge separation, and inverted bulk heterojunction solar cell application of phenothiazine-fullerene dyads', ACS Applied Materials & Interfaces, vol. 8, no. 13, pp. 8481-8490. https://doi.org/10.1021/acsami.6b00561

Syntheses, charge separation, and inverted bulk heterojunction solar cell application of phenothiazine-fullerene dyads. / Blanco, Gwendolyn D.; Hiltunen, Arto J.; Lim, Gary N.; KC, Chandra B.; Kaunisto, Kimmo M.; Vuorinen, Tommi; Nesterov, Vladimir N.; Lemmetyinen, Helge J.; D'Souza, Francis.

In: ACS Applied Materials & Interfaces, Vol. 8, No. 13, 2016, p. 8481-8490.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Syntheses, charge separation, and inverted bulk heterojunction solar cell application of phenothiazine-fullerene dyads

AU - Blanco, Gwendolyn D.

AU - Hiltunen, Arto J.

AU - Lim, Gary N.

AU - KC, Chandra B.

AU - Kaunisto, Kimmo M.

AU - Vuorinen, Tommi

AU - Nesterov, Vladimir N.

AU - Lemmetyinen, Helge J.

AU - D'Souza, Francis

PY - 2016

Y1 - 2016

N2 - A series of phenothiazine-fulleropyrrolidine (PTZ-C60) dyads having fullerene either at the C-3 aromatic ring position or at the N-position of phenothiazine macrocycle were newly synthesized and characterized. Photoinduced electron transfer leading to PTZ ?+-C60 ?- charge-separated species was established from studies involving femtosecond transient absorption spectroscopy. Because of the close proximity of the donor and acceptor entities, the C-3 ring substituted PTZ-C60 dyads revealed faster charge separation and charge recombination processes than that observed in the dyad functionalized through the N-position. Next, inverted organic bulk heterojunction (BHJ) solar cells were constructed using the dyads in place of traditionally used [6,6]-phenyl-C61- butyric acid methyl ester (PCBM) and an additional electron donor material poly(3-hexylthiophene) (P3HT). The performance of the C-3 ring substituted PTZ-C60 dyad having a polyethylene glycol substituent produced a power conversion efficiency of 3.5% under inverted bulk heterojunction (BHJ) configuration. This was attributed to optimal BHJ morphology between the polymer and the dyad, which was further promoted by the efficient intramolecular charge separation and relatively slow charge recombination promoted by the dyad within the BHJ structure. The present finding demonstrate PTZ-C60 dyads as being good prospective materials for building organic photovoltaic devices.

AB - A series of phenothiazine-fulleropyrrolidine (PTZ-C60) dyads having fullerene either at the C-3 aromatic ring position or at the N-position of phenothiazine macrocycle were newly synthesized and characterized. Photoinduced electron transfer leading to PTZ ?+-C60 ?- charge-separated species was established from studies involving femtosecond transient absorption spectroscopy. Because of the close proximity of the donor and acceptor entities, the C-3 ring substituted PTZ-C60 dyads revealed faster charge separation and charge recombination processes than that observed in the dyad functionalized through the N-position. Next, inverted organic bulk heterojunction (BHJ) solar cells were constructed using the dyads in place of traditionally used [6,6]-phenyl-C61- butyric acid methyl ester (PCBM) and an additional electron donor material poly(3-hexylthiophene) (P3HT). The performance of the C-3 ring substituted PTZ-C60 dyad having a polyethylene glycol substituent produced a power conversion efficiency of 3.5% under inverted bulk heterojunction (BHJ) configuration. This was attributed to optimal BHJ morphology between the polymer and the dyad, which was further promoted by the efficient intramolecular charge separation and relatively slow charge recombination promoted by the dyad within the BHJ structure. The present finding demonstrate PTZ-C60 dyads as being good prospective materials for building organic photovoltaic devices.

KW - fullerene

KW - phenothiazine

KW - photoinduced electron transfer

KW - femtosecond transient spectroscopy

KW - inverted bulk heterojunction

KW - organic photovoltaics

U2 - 10.1021/acsami.6b00561

DO - 10.1021/acsami.6b00561

M3 - Article

VL - 8

SP - 8481

EP - 8490

JO - ACS Applied Materials & Interfaces

JF - ACS Applied Materials & Interfaces

SN - 1944-8244

IS - 13

ER -