Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses

Ted M. Pappenfus; Furqan Almyahi; Nathan A. Cooling; Evan W. Culver; Seth C. Rasmussen; Paul C. Dastoor

doi:10.1002/macp.201800272

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses

Ted M. Pappenfus, Furqan Almyahi, Nathan A. Cooling, Evan W. Culver, Seth C. Rasmussen, Paul C. Dastoor

Chemistry (Morris)

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

24 Scopus citations

Abstract

This study reports the scalability of direct arylation polymerization (DArP) batch reactions for the preparation of poly(3-hexylthiophene) (P3HT) using the Herrmann–Beller catalyst combined with a tertiary phosphine in the green solvent 2-methyltetrahydrofuran on scales ranging from 0.5 to 10 g. The physical properties of these DArP polymers are compared to those resulting from P3HT prepared via Grignard metathesis (GRIM) on a 130 g scale. Both DArP and GRIM methods are found to produce highly regioregular polymers with no evidence of β-defects and the polymers are found to exhibit comparable device performance as donor materials in bulk heterojunction organic solar cells. Purification studies coupled with device measurements highlight the necessity to carefully address the presence of impurities in materials produced from large-scale DArP batch reactions. Economic analyses reveal that the cost involved in the preparation of P3HT via DArP or GRIM procedures are comparable per gram of product and show that the most expensive component is unique for each method.

Original language	English (US)
Article number	1800272
Journal	Macromolecular Chemistry and Physics
Volume	219
Issue number	21
DOIs	https://doi.org/10.1002/macp.201800272
State	Published - Nov 2018

Bibliographical note

Funding Information:
T.M.P. acknowledges the following: i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research, the UMM Division of Science and Mathematics, and the Howard Hughes Medical Institute (HHMI) Pathways to Science Program for financial assistance, ii) Eric King and Nathan Ferrey for investigating the very first DArP reactions in green solvents in 2014, and iii) Andrew J. Helmin and Wyatt D. Wilcox for assistance with the GPC experiments and for helpful discussions. S.C.R. acknowledges the Australian-American Fulbright Commission and North Dakota State University for financial support. The work was performed in part at the Materials node of the Australian National Fabrication Facility, a company established under the National Collaborative Research Infrastructure Strategy to provide nano-and micro-fabrication facilities for Australia’s researchers.

Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

direct arylation scalability
organic solar cells
polythiophenes

UN SDGs

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

Publisher link

10.1002/macp.201800272

Find It

Find It at U of M Libraries

Cite this

Pappenfus, T. M., Almyahi, F., Cooling, N. A., Culver, E. W., Rasmussen, S. C., & Dastoor, P. C. (2018). Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses. Macromolecular Chemistry and Physics, 219(21), Article 1800272. https://doi.org/10.1002/macp.201800272

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses. / Pappenfus, Ted M.; Almyahi, Furqan; Cooling, Nathan A. et al.
In: Macromolecular Chemistry and Physics, Vol. 219, No. 21, 1800272, 11.2018.

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

@article{8f348cc8625c4c5990699e8e157b462a,

title = "Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses",

abstract = "This study reports the scalability of direct arylation polymerization (DArP) batch reactions for the preparation of poly(3-hexylthiophene) (P3HT) using the Herrmann–Beller catalyst combined with a tertiary phosphine in the green solvent 2-methyltetrahydrofuran on scales ranging from 0.5 to 10 g. The physical properties of these DArP polymers are compared to those resulting from P3HT prepared via Grignard metathesis (GRIM) on a 130 g scale. Both DArP and GRIM methods are found to produce highly regioregular polymers with no evidence of β-defects and the polymers are found to exhibit comparable device performance as donor materials in bulk heterojunction organic solar cells. Purification studies coupled with device measurements highlight the necessity to carefully address the presence of impurities in materials produced from large-scale DArP batch reactions. Economic analyses reveal that the cost involved in the preparation of P3HT via DArP or GRIM procedures are comparable per gram of product and show that the most expensive component is unique for each method.",

keywords = "direct arylation scalability, organic solar cells, polythiophenes",

author = "Pappenfus, \{Ted M.\} and Furqan Almyahi and Cooling, \{Nathan A.\} and Culver, \{Evan W.\} and Rasmussen, \{Seth C.\} and Dastoor, \{Paul C.\}",

note = "Funding Information: T.M.P. acknowledges the following: i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research, the UMM Division of Science and Mathematics, and the Howard Hughes Medical Institute (HHMI) Pathways to Science Program for financial assistance, ii) Eric King and Nathan Ferrey for investigating the very first DArP reactions in green solvents in 2014, and iii) Andrew J. Helmin and Wyatt D. Wilcox for assistance with the GPC experiments and for helpful discussions. S.C.R. acknowledges the Australian-American Fulbright Commission and North Dakota State University for financial support. The work was performed in part at the Materials node of the Australian National Fabrication Facility, a company established under the National Collaborative Research Infrastructure Strategy to provide nano-and micro-fabrication facilities for Australia{\textquoteright}s researchers. Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = nov,

doi = "10.1002/macp.201800272",

language = "English (US)",

volume = "219",

journal = "Macromolecular Chemistry and Physics",

issn = "1022-1352",

publisher = "Wiley-VCH Verlag",

number = "21",

}

TY - JOUR

T1 - Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials

T2 - Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses

AU - Pappenfus, Ted M.

AU - Almyahi, Furqan

AU - Cooling, Nathan A.

AU - Culver, Evan W.

AU - Rasmussen, Seth C.

AU - Dastoor, Paul C.

N1 - Funding Information: T.M.P. acknowledges the following: i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research, the UMM Division of Science and Mathematics, and the Howard Hughes Medical Institute (HHMI) Pathways to Science Program for financial assistance, ii) Eric King and Nathan Ferrey for investigating the very first DArP reactions in green solvents in 2014, and iii) Andrew J. Helmin and Wyatt D. Wilcox for assistance with the GPC experiments and for helpful discussions. S.C.R. acknowledges the Australian-American Fulbright Commission and North Dakota State University for financial support. The work was performed in part at the Materials node of the Australian National Fabrication Facility, a company established under the National Collaborative Research Infrastructure Strategy to provide nano-and micro-fabrication facilities for Australia’s researchers. Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/11

Y1 - 2018/11

N2 - This study reports the scalability of direct arylation polymerization (DArP) batch reactions for the preparation of poly(3-hexylthiophene) (P3HT) using the Herrmann–Beller catalyst combined with a tertiary phosphine in the green solvent 2-methyltetrahydrofuran on scales ranging from 0.5 to 10 g. The physical properties of these DArP polymers are compared to those resulting from P3HT prepared via Grignard metathesis (GRIM) on a 130 g scale. Both DArP and GRIM methods are found to produce highly regioregular polymers with no evidence of β-defects and the polymers are found to exhibit comparable device performance as donor materials in bulk heterojunction organic solar cells. Purification studies coupled with device measurements highlight the necessity to carefully address the presence of impurities in materials produced from large-scale DArP batch reactions. Economic analyses reveal that the cost involved in the preparation of P3HT via DArP or GRIM procedures are comparable per gram of product and show that the most expensive component is unique for each method.

AB - This study reports the scalability of direct arylation polymerization (DArP) batch reactions for the preparation of poly(3-hexylthiophene) (P3HT) using the Herrmann–Beller catalyst combined with a tertiary phosphine in the green solvent 2-methyltetrahydrofuran on scales ranging from 0.5 to 10 g. The physical properties of these DArP polymers are compared to those resulting from P3HT prepared via Grignard metathesis (GRIM) on a 130 g scale. Both DArP and GRIM methods are found to produce highly regioregular polymers with no evidence of β-defects and the polymers are found to exhibit comparable device performance as donor materials in bulk heterojunction organic solar cells. Purification studies coupled with device measurements highlight the necessity to carefully address the presence of impurities in materials produced from large-scale DArP batch reactions. Economic analyses reveal that the cost involved in the preparation of P3HT via DArP or GRIM procedures are comparable per gram of product and show that the most expensive component is unique for each method.

KW - direct arylation scalability

KW - organic solar cells

KW - polythiophenes

UR - https://www.scopus.com/pages/publications/85054353202

UR - https://www.scopus.com/inward/citedby.url?scp=85054353202&partnerID=8YFLogxK

U2 - 10.1002/macp.201800272

DO - 10.1002/macp.201800272

M3 - Article

AN - SCOPUS:85054353202

SN - 1022-1352

VL - 219

JO - Macromolecular Chemistry and Physics

JF - Macromolecular Chemistry and Physics

IS - 21

M1 - 1800272

ER -

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale-Up, Solar Cell Performance, and Cost Analyses

Abstract

Bibliographical note

Keywords

UN SDGs

Publisher link

Find It

Other files and links

Fingerprint

Cite this