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Regioisomerically Pure 1,7-Dicyanoperylene Diimide Dimer for Charge Extraction from Donors with High Electron Affinities.
ACS Omega ( IF 3.7 ) Pub Date : 2020-06-29 , DOI: 10.1021/acsomega.0c01217
Richard D Pettipas 1 , Chase L Radford 1 , Timothy L Kelly 1
Affiliation  

Perylene diimide (PDI) has attracted widespread interest as an inexpensive electron acceptor for photovoltaic applications; however, overcrystallization in the bulk heterojunction typically leads to low device performance. Recent work has addressed this issue by forming bay-linked PDI dimers and oligomers, where the steric bulk of adjacent PDI units forces the molecule to adopt a nonplanar structure. This disrupts the molecular packing and limits domain sizes in the bulk heterojunction. Unfortunately, the introduction of electron-donating/-withdrawing groups in the bay region is also the best way to fine-tune the frontier molecular orbitals (FMOs) of PDI, which is highly desirable from a device optimization standpoint. This competition for the bay region has made it difficult for PDI to keep pace with other non-fullerene acceptors. Here, we report the synthesis of regioisomerically pure 1,7-dicyanoperylene diimide and its dimerization through an imide linkage. We show that this is an effective strategy to tune the energies of the FMOs while simultaneously suppressing overcrystallization in the bulk heterojunction. The resulting acceptor has a low LUMO energy of −4.2 eV and is capable of accepting photogenerated electrons from donor polymers with high electron affinities, even when conventional acceptors such as PDI, PC71BM, and ITIC cannot.

中文翻译:

区域异构纯的1,7-二氰基亚丙基二亚胺二聚体,用于从具有高电子亲和力的供体中提取电荷。

as二酰亚胺(PDI)作为一种廉价的光伏电子受体已经引起了广泛的关注。然而,体异质结中的过结晶通常导致器件性能低下。最近的工作通过形成海湾连接的PDI二聚体和寡聚体解决了这个问题,其中相邻PDI单元的空间体积迫使分子采用非平面结构。这破坏了分子堆积并限制了本体异质结中的域大小。不幸的是,在海湾区域引入给电子/吸电子基团也是微调PDI前沿分子轨道(FMO)的最佳方法,从设备优化的角度来看,这是非常需要的。海湾地区的竞争使PDI难以与其他非富勒烯受体并驾齐驱。这里,我们报道了区域异构纯的1,7-二氰基亚丙基二酰亚胺的合成及其通过酰亚胺键的二聚作用。我们表明,这是一种有效的策略,可调节FMO的能量,同时抑制本体异质结中的过结晶。所得的受体具有−4.2 eV的低LUMO能量,即使在常规受体(例如PDI,PC)下,也能够接受具有高电子亲和力的供体聚合物产生的光生电子71 BM,而ITIC不能。
更新日期:2020-07-14
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