Diketopyrrolopyrrole Derivatives Functionalized with N‐Annulated PDI and Se‐Annulated PDI by Direct (Hetero)Arylation Methods. Issue 9 (23rd March 2020)

• Record Type: Journal Article
• Authors: Welsh, Thomas A.; Nazari, Maryam; Welch, Gregory C.
• Is Part Of: Asian journal of organic chemistry. Volume 9:Issue 9(2020)
• Page Start: 1291
• Page End: 1300
• Publication Date: 2020-03-23
• Subjects: Diketopyrrolopyrrole -- Perylene Diimide -- Organic Photovoltaics -- Solvent Vapor Annealing -- Direct (Hetero)Arylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202000106
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: We report on the synthesis of diketopyrrolopyrrole (DPP) derivatives functionalized with N‐annulated and Se‐annulated perylene diimide (NPDI and SePDI, respectively) via direct (hetero)arylation methods. DPP is symmetrically bifunctionalized with SePDI (SePDI−DPP−SePDI) and unsymmetrically functionalized with SePDI and NPDI (SePDI−DPP−NPDI). The effects of Se substitution compared to N substitution on physical, electrochemical, and optical properties are investigated along with performance as non‐fullerene acceptors in photovoltaic devices. It is found that Se substitution increases the electron affinity of the π‐conjugated molecule and blue shifts the optical absorption spectra, observations that were supported by computational analysis. Steric strain between the PDI endcap and DPP core prevent complete electronic communication along the π‐conjugated backbone and results in the unsymmetrical compound, SePDI−DPP−NPDI, having electronic and optical properties that are a linear combination of both the symmetrical SePDI and NPDI based compounds. The SePDI−DPP−NPDI compound has a distinct melt observed at 343 °C and organic photovoltaic devices based on this compound had lower than expected open‐circuit voltages, suggesting a unique solid‐state packing arrangement. SePDI‐based compounds performed worse than the NPDI‐based compound in organic photovoltaic devices using the donor polymer PTB7‐Th. Abstract : Two new non‐fullerene acceptors are presented. The molecules are comprised of a diketopyrrolopyrrole core with perlyene diimide endcaps and were syntheszied using direct (hetero)arylation cross‐coupling. The effect of Se and N annulation at the bay position of perylene diimide on materials physical, optical, and electrochemical properties were investigated. Organic photovolatic devices were evlauted using the molecules as non‐fullerene acceptors paired with the donor polymer PTB7‐Th.