Strategic Fluorination of Polymers and Fullerenes Improves Photostability of Organic Photovoltaic Blends

Wade Braunecker; Andrew Ferguson; Jason Pfeilsticker; Bryon Larson; Vinila Viswanathan; Colin Brook; Steven Strauss; Olga Boltalina; Praveen Ramamurthy; Logan Garner

doi:10.1016/j.orgel.2018.08.045

Strategic Fluorination of Polymers and Fullerenes Improves Photostability of Organic Photovoltaic Blends

Wade Braunecker, Andrew Ferguson, Jason Pfeilsticker, Bryon Larson, Vinila Viswanathan, Colin Brook, Steven Strauss, Olga Boltalina, Praveen Ramamurthy, Logan Garner

Chemistry and Nanoscience

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

5 Scopus Citations

Abstract

The photobleaching dynamics of a series of three organic photovoltaic (OPV) donor polymer blends with five different fullerenes are presented. The fullerenes studied include PC₆₀BM and four perfluoroalkylfullerenes with relatively large electron affinities, namely C₆₀(CF₃)₂, C₆₀(i-C₃F₇)₂, C₆₀(CF₃)₄, and C₆₀(CF₃)₈. The donor polymers were all based on cyclopentadithiophene (CPDT) and thienopyrrolodione (TPD), but the TPD side chains were designed to include alkyl, partially fluorinated alkyl, and fluorinated phenyl groups to improve miscibility of the active layer components. Exciton harvesting was probed with photoluminescence quenching measurements. Accelerated photodegradation studies of polymer:fullerene blends were then carried out under white light illumination at ∼1.2 suns in air. A strong correlation was observed between the polymer donor photobleaching rate and the electron affinity of the fullerene. The most dramatic effect was observed for a blend of C₆₀(CF₃)₈ with the donor containing fluorinated phenyl groups: the blend required 150 times the dosing of photons to bleach to 80% of its initial optical density than an analagous blend of PC₆₀BM and non-fluorinated donor polymer. These results ultimately suggest that appropriate fluorination strategies applied to both the donor and acceptor can be a viable route toward a new paradigm of intrinsically photo- and phase-stable OPV active layers.

Original language	American English
Pages (from-to)	685-694
Number of pages	10
Journal	Organic Electronics
Volume	62
DOIs	https://doi.org/10.1016/j.orgel.2018.08.045 https://doi.org/10.1016/j.orgel.2018.08.045
State	Published - Nov 2018

Bibliographical note

Publisher Copyright:
© 2018 Elsevier B.V.

NREL Publication Number

NREL/JA-5900-71422

Keywords

Organic photovoltaics
Perfluoroalkylated fullerenes
Photodegradation
Photoluminescence quenching
Photostability

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Braunecker, W., Ferguson, A., Pfeilsticker, J., Larson, B., Viswanathan, V., Brook, C., Strauss, S., Boltalina, O., Ramamurthy, P., & Garner, L. (2018). Strategic Fluorination of Polymers and Fullerenes Improves Photostability of Organic Photovoltaic Blends. Organic Electronics, 62, 685-694. https://doi.org/10.1016/j.orgel.2018.08.045, https://doi.org/10.1016/j.orgel.2018.08.045

@article{96cbe926dcfe494f8137811fdb3af088,

title = "Strategic Fluorination of Polymers and Fullerenes Improves Photostability of Organic Photovoltaic Blends",

abstract = "The photobleaching dynamics of a series of three organic photovoltaic (OPV) donor polymer blends with five different fullerenes are presented. The fullerenes studied include PC60BM and four perfluoroalkylfullerenes with relatively large electron affinities, namely C60(CF3)2, C60(i-C3F7)2, C60(CF3)4, and C60(CF3)8. The donor polymers were all based on cyclopentadithiophene (CPDT) and thienopyrrolodione (TPD), but the TPD side chains were designed to include alkyl, partially fluorinated alkyl, and fluorinated phenyl groups to improve miscibility of the active layer components. Exciton harvesting was probed with photoluminescence quenching measurements. Accelerated photodegradation studies of polymer:fullerene blends were then carried out under white light illumination at ∼1.2 suns in air. A strong correlation was observed between the polymer donor photobleaching rate and the electron affinity of the fullerene. The most dramatic effect was observed for a blend of C60(CF3)8 with the donor containing fluorinated phenyl groups: the blend required 150 times the dosing of photons to bleach to 80% of its initial optical density than an analagous blend of PC60BM and non-fluorinated donor polymer. These results ultimately suggest that appropriate fluorination strategies applied to both the donor and acceptor can be a viable route toward a new paradigm of intrinsically photo- and phase-stable OPV active layers.",

keywords = "Organic photovoltaics, Perfluoroalkylated fullerenes, Photodegradation, Photoluminescence quenching, Photostability",

author = "Wade Braunecker and Andrew Ferguson and Jason Pfeilsticker and Bryon Larson and Vinila Viswanathan and Colin Brook and Steven Strauss and Olga Boltalina and Praveen Ramamurthy and Logan Garner",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",

year = "2018",

month = nov,

doi = "10.1016/j.orgel.2018.08.045",

language = "American English",

volume = "62",

pages = "685--694",

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Braunecker, W , Ferguson, A, Pfeilsticker, J, Larson, B, Viswanathan, V, Brook, C, Strauss, S, Boltalina, O, Ramamurthy, P & Garner, L 2018, 'Strategic Fluorination of Polymers and Fullerenes Improves Photostability of Organic Photovoltaic Blends', Organic Electronics, vol. 62, pp. 685-694. https://doi.org/10.1016/j.orgel.2018.08.045, https://doi.org/10.1016/j.orgel.2018.08.045

TY - JOUR

T1 - Strategic Fluorination of Polymers and Fullerenes Improves Photostability of Organic Photovoltaic Blends

AU - Braunecker, Wade

AU - Ferguson, Andrew

AU - Pfeilsticker, Jason

AU - Larson, Bryon

AU - Viswanathan, Vinila

AU - Brook, Colin

AU - Strauss, Steven

AU - Boltalina, Olga

AU - Ramamurthy, Praveen

AU - Garner, Logan

PY - 2018/11

Y1 - 2018/11

N2 - The photobleaching dynamics of a series of three organic photovoltaic (OPV) donor polymer blends with five different fullerenes are presented. The fullerenes studied include PC60BM and four perfluoroalkylfullerenes with relatively large electron affinities, namely C60(CF3)2, C60(i-C3F7)2, C60(CF3)4, and C60(CF3)8. The donor polymers were all based on cyclopentadithiophene (CPDT) and thienopyrrolodione (TPD), but the TPD side chains were designed to include alkyl, partially fluorinated alkyl, and fluorinated phenyl groups to improve miscibility of the active layer components. Exciton harvesting was probed with photoluminescence quenching measurements. Accelerated photodegradation studies of polymer:fullerene blends were then carried out under white light illumination at ∼1.2 suns in air. A strong correlation was observed between the polymer donor photobleaching rate and the electron affinity of the fullerene. The most dramatic effect was observed for a blend of C60(CF3)8 with the donor containing fluorinated phenyl groups: the blend required 150 times the dosing of photons to bleach to 80% of its initial optical density than an analagous blend of PC60BM and non-fluorinated donor polymer. These results ultimately suggest that appropriate fluorination strategies applied to both the donor and acceptor can be a viable route toward a new paradigm of intrinsically photo- and phase-stable OPV active layers.

AB - The photobleaching dynamics of a series of three organic photovoltaic (OPV) donor polymer blends with five different fullerenes are presented. The fullerenes studied include PC60BM and four perfluoroalkylfullerenes with relatively large electron affinities, namely C60(CF3)2, C60(i-C3F7)2, C60(CF3)4, and C60(CF3)8. The donor polymers were all based on cyclopentadithiophene (CPDT) and thienopyrrolodione (TPD), but the TPD side chains were designed to include alkyl, partially fluorinated alkyl, and fluorinated phenyl groups to improve miscibility of the active layer components. Exciton harvesting was probed with photoluminescence quenching measurements. Accelerated photodegradation studies of polymer:fullerene blends were then carried out under white light illumination at ∼1.2 suns in air. A strong correlation was observed between the polymer donor photobleaching rate and the electron affinity of the fullerene. The most dramatic effect was observed for a blend of C60(CF3)8 with the donor containing fluorinated phenyl groups: the blend required 150 times the dosing of photons to bleach to 80% of its initial optical density than an analagous blend of PC60BM and non-fluorinated donor polymer. These results ultimately suggest that appropriate fluorination strategies applied to both the donor and acceptor can be a viable route toward a new paradigm of intrinsically photo- and phase-stable OPV active layers.

KW - Organic photovoltaics

KW - Perfluoroalkylated fullerenes

KW - Photodegradation

KW - Photoluminescence quenching

KW - Photostability

UR - http://www.scopus.com/inward/record.url?scp=85057200335&partnerID=8YFLogxK

U2 - 10.1016/j.orgel.2018.08.045

DO - 10.1016/j.orgel.2018.08.045

M3 - Article

AN - SCOPUS:85057200335

SN - 1566-1199

VL - 62

SP - 685

EP - 694

JO - Organic Electronics

JF - Organic Electronics

ER -

Strategic Fluorination of Polymers and Fullerenes Improves Photostability of Organic Photovoltaic Blends

Abstract

Bibliographical note

NREL Publication Number

Keywords

UN SDGs

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