Diketopyrrolopyrrole Derivatives Functionalized with N‐Annulated PDI and Se‐Annulated PDI by Direct (Hetero)Arylation Methods,Asian Journal of Organic Chemistry

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Diketopyrrolopyrrole Derivatives Functionalized with N‐Annulated PDI and Se‐Annulated PDI by Direct (Hetero)Arylation Methods
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-03-23 , DOI: 10.1002/ajoc.202000106
Thomas A. Welsh ₁ , Maryam Nazari ₁ , Gregory C. Welch ₁

Affiliation

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.

中文翻译：

通过直接（杂）化方法用N环化PDI和Se环化PDI官能化的二酮吡咯并吡咯衍生物

我们对用N -环化和Se -环苝二酰亚胺（分别NPDI和SePDI，）二酮吡咯并吡咯官能（DPP）衍生物的合成报告经由直接（杂）芳构化方法。DPP使用SePDI（SePDI-DPP-SePDI）对称地双功能化，而使用SePDI和NPDI（SePDI-DPP-NPDI）则不对称地功能化。研究了硒取代与氮取代对物理，电化学和光学性质的影响，以及在光伏器件中作为非富勒烯受体的性能。研究发现，硒取代增加了π共轭分子的电子亲和力，使蓝光吸收光谱发生位移，这得到了计算分析的支持。PDI端盖和DPP核心之间的立体应变阻止了沿π共轭骨架的完全电子通讯，并导致了不对称化合物SePDI-DPP-NPDI，具有对称的SePDI和NPDI基化合物线性结合的电子和光学特性。SePDI-DPP-NPDI化合物在343°C时观察到明显的熔体，基于该化合物的有机光伏器件的开路电压低于预期，表明其独特的固态填料布置。使用供体聚合物PTB7-Th的有机光伏器件中，基于SePDI的化合物的性能比基于NPDI的化合物差。

更新日期：2020-03-23

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