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

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

Journal Article · Fri Aug 10 00:00:00 EDT 2018 · Asian Journal of Organic Chemistry

DOI:https://doi.org/10.1002/ajoc.201800360· OSTI ID:1463921

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

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.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1463921

Journal Information:: Asian Journal of Organic Chemistry, Journal Name: Asian Journal of Organic Chemistry Journal Issue: 11 Vol. 7; ISSN 2193-5807

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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