Bis‐isoindigos: New Electron‐Deficient Building Blocks for Constructing Conjugated Polymers with Extended Electron Delocalization

Luo, Xuyi; Tran, Dung T.; Sun, Hong; Mi, Tianxiong; Kadlubowski, Natalie M.; Zhao, Yan; Zhao, Kejie; Mei, Jianguo

doi:10.1002/ajoc.201800360

Title: Bis‐isoindigos: New Electron‐Deficient Building Blocks for Constructing Conjugated Polymers with Extended Electron Delocalization

Abstract

Abstract Incorporation of acceptor‐acceptor (A‐A) type moieties into donor‐acceptor (D‐A) type conjugated polymers becomes a new strategy to tune their electronic properties. In this work, we first demonstrate an efficient convergent route to prepare isoindigo‐based A‐A type building blocks ‐ bis‐isoindigos ‐ via the palladium‐catalyzed oxidative coupling. Bis‐isoindigo‐based polymers show high planarity and delocalized frontier molecular orbitals with lowered LUMO and intact HOMO energy levels, in comparison with their corresponding mono‐isoindigo counterparts. Moreover, fluorine substitution on donors only lowers HOMO levels of Bis‐IID polymers. This study asserts that the D‐A‐A strategy is effective in selectively tuning FMO energy levels of conjugated polymers, complementary to the D‐D‐A approach for the HOMO energy level tuning.

Authors:

Luo, Xuyi ^[1]; Tran, Dung T. ^[1]; Sun, Hong ^[2]; Mi, Tianxiong ^[3]; Kadlubowski, Natalie M. ^[1]; Zhao, Yan ^[1]; Zhao, Kejie ^[2];

^[1]

Department of Chemistry Purdue University 560 Oval Drive West Lafayette Indiana 47907 United States
School of Mechanical Engineering 560 Oval Drive West Lafayette Indiana 47907 United States
College of Chemistry and Molecular Engineering Peking University Beijing China

Publication Date:: Fri Aug 10 00:00:00 EDT 2018

Sponsoring Org.:: USDOE

OSTI Identifier:: 1463921

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Asian Journal of Organic Chemistry

Additional Journal Information:: Journal Name: Asian Journal of Organic Chemistry Journal Volume: 7 Journal Issue: 11; Journal ID: ISSN 2193-5807

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Luo, Xuyi, Tran, Dung T., Sun, Hong, Mi, Tianxiong, Kadlubowski, Natalie M., Zhao, Yan, Zhao, Kejie, and Mei, Jianguo. Bis‐isoindigos: New Electron‐Deficient Building Blocks for Constructing Conjugated Polymers with Extended Electron Delocalization.  Germany: N. p., 2018. 
Web.  doi:10.1002/ajoc.201800360.

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                    Luo, Xuyi, Tran, Dung T., Sun, Hong, Mi, Tianxiong, Kadlubowski, Natalie M., Zhao, Yan, Zhao, Kejie, & Mei, Jianguo. Bis‐isoindigos: New Electron‐Deficient Building Blocks for Constructing Conjugated Polymers with Extended Electron Delocalization.  Germany.  https://doi.org/10.1002/ajoc.201800360

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                    Luo, Xuyi, Tran, Dung T., Sun, Hong, Mi, Tianxiong, Kadlubowski, Natalie M., Zhao, Yan, Zhao, Kejie, and Mei, Jianguo. Fri .  
"Bis‐isoindigos: New Electron‐Deficient Building Blocks for Constructing Conjugated Polymers with Extended Electron Delocalization".  Germany.  https://doi.org/10.1002/ajoc.201800360.

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@article{osti_1463921,

  title        = {Bis‐isoindigos: New Electron‐Deficient Building Blocks for Constructing Conjugated Polymers with Extended Electron Delocalization},

  author       = {Luo, Xuyi and Tran, Dung T. and Sun, Hong and Mi, Tianxiong and Kadlubowski, Natalie M. and Zhao, Yan and Zhao, Kejie and Mei, Jianguo},

  abstractNote = {Abstract Incorporation of acceptor‐acceptor (A‐A) type moieties into donor‐acceptor (D‐A) type conjugated polymers becomes a new strategy to tune their electronic properties. In this work, we first demonstrate an efficient convergent route to prepare isoindigo‐based A‐A type building blocks ‐ bis‐isoindigos ‐ via the palladium‐catalyzed oxidative coupling. Bis‐isoindigo‐based polymers show high planarity and delocalized frontier molecular orbitals with lowered LUMO and intact HOMO energy levels, in comparison with their corresponding mono‐isoindigo counterparts. Moreover, fluorine substitution on donors only lowers HOMO levels of Bis‐IID polymers. This study asserts that the D‐A‐A strategy is effective in selectively tuning FMO energy levels of conjugated polymers, complementary to the D‐D‐A approach for the HOMO energy level tuning.},

  doi          = {10.1002/ajoc.201800360},

  journal      = {Asian Journal of Organic Chemistry},

  number       = 11,

  volume       = 7,

  place        = {Germany},

  year         = {Fri Aug 10 00:00:00 EDT 2018},

  month        = {Fri Aug 10 00:00:00 EDT 2018}

}

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Title: Bis‐isoindigos: New Electron‐Deficient Building Blocks for Constructing Conjugated Polymers with Extended Electron Delocalization

Abstract

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Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells
journal, January 2015

Bithienopyrroledione-Based Copolymers, Versatile Semiconductors for Balanced Ambipolar Thin-Film Transistors and Organic Solar Cells with V _oc > 1 V
journal, December 2016

High-Performance Hole Transport and Quasi-Balanced Ambipolar OFETs Based on D-A-A Thieno-benzo-isoindigo Polymers
journal, January 2016

High Performance Weak Donor–Acceptor Polymers in Thin Film Transistors: Effect of the Acceptor on Electronic Properties, Ambipolar Conductivity, Mobility, and Thermal Stability
journal, December 2011