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

Journal Article · · Asian Journal of Organic Chemistry
 [1];  [1];  [2];  [3];  [1];  [1];  [2]; ORCiD logo [1]
  1. Department of Chemistry Purdue University 560 Oval Drive West Lafayette Indiana 47907 United States
  2. School of Mechanical Engineering 560 Oval Drive West Lafayette Indiana 47907 United States
  3. College of Chemistry and Molecular Engineering Peking University Beijing China
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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.

Sponsoring Organization:
USDOE
OSTI ID:
1463921
Journal Information:
Asian Journal of Organic Chemistry, Journal Name: Asian Journal of Organic Chemistry Vol. 7 Journal Issue: 11; ISSN 2193-5807
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English
Citation Metrics:
Cited by: 14 works
Citation information provided by
Web of Science

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