Regioisomerically Pure 1,7-Dicyanoperylene Diimide Dimer for Charge Extraction from Donors with High Electron Affinities

ACS Omega
Richard D PettipasTimothy L Kelly

Abstract

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 d...Continue Reading

References

Jan 13, 2010·Chemical Reviews·Tracey M Clarke, James R Durrant
Jun 22, 2013·Advanced Materials·Alexander SharenkoGuillermo C Bazan
Jul 2, 2014·The Journal of Organic Chemistry·Sanchita SenguptaWolter F Jager
Sep 6, 2012·The Journal of Physical Chemistry Letters·Sridhar RajaramK S Narayan
Jan 24, 2018·Nature Materials·Jianhui HouFeng Gao
Mar 21, 2018·Chemical Reviews·Guangye ZhangHe Yan
Jun 15, 2018·Advanced Materials·Caitlin McDowellGuillermo C Bazan
Aug 11, 2018·Science·Lingxian MengYongsheng Chen

❮ Previous
Next ❯

Methods Mentioned

BETA
atomic force microscopy
AFM
NMR

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Peritoneal Dialysis International : Journal of the International Society for Peritoneal Dialysis
Peter G Blake
Journal of Prosthodontics : Official Journal of the American College of Prosthodontists
Richard A Williamson
© 2021 Meta ULC. All rights reserved