Pyridinium-Functionalized Pyromellitic Diimides with Stabilized Radical Anion States

ACS Omega
Andrew J GreenleeDennis D Cao

Abstract

In this work, we report the stabilization of the reduced states of pyromellitic diimide by charge-balancing the imide radical anions with cationic pyridinium groups attached to the aromatic core. This structural modification is confirmed by single-crystal X-ray diffraction analysis. Characterization by (spectro)electrochemical experiments and computations reveal that the addition of cationic groups to an already electron-deficient ring system results in up to +0.57 V shifts in reduction potentials, largely as a consequence of charge screening and lowest unoccupied molecular orbital-lowering effects. This formal charge-balancing approach to stabilizing the reduced states of electron-deficient pyromellitic diimides will facilitate their incorporation into spin-based optoelectronic materials and devices.

References

Dec 8, 2005·The Journal of Physical Chemistry. a·Alison FunstonJosef Michl
Jan 17, 2008·Chemical Society Reviews·Sheshanath V BhosaleSteven J Langford
Oct 10, 2008·Journal of the American Chemical Society·Qingdong ZhengHoward E Katz
Dec 15, 2010·Advanced Materials·Xiaowei ZhanSeth R Marder
May 10, 2011·Chemical Society Reviews·Stefano Sanvito
Jan 26, 2013·Science·Jonathan C BarnesJ Fraser Stoddart
Sep 5, 2013·Nature Nanotechnology·Christoph Boehme, John M Lupton
Jun 26, 2014·Angewandte Chemie·Sabin-Lucian Suraru, Frank Würthner
Nov 14, 2014·Angewandte Chemie·David SchmidtFrank Würthner
Jan 13, 2015·The Journal of Organic Chemistry·Nolan M GallagherAndrzej Rajca
Nov 26, 2015·Angewandte Chemie·Prince RavatMichal Juríček
May 4, 2016·Chemistry : a European Journal·Han ZhouTongxiang Fan
Aug 16, 2016·ACS Applied Materials & Interfaces·Adriana IordacheLionel Picard
Aug 27, 2016·Chemical Reviews·Mohammad Al KobaisiSheshanath V Bhosale
Apr 25, 2017·Journal of the American Chemical Society·Dong Jun KimJ Fraser Stoddart

❮ Previous
Next ❯

Citations

Oct 15, 2019·Chemistry : a European Journal·Min Ji KimDennis D Cao
Jun 19, 2018·Chemical Communications : Chem Comm·Teck Lip Dexter TamJishan Wu
Jul 19, 2019·The Journal of Organic Chemistry·Stella M LuoDennis D Cao

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray

Software Mentioned

CrystalStructure
POV
SHELXL97
Visual Molecular Dynamics ( VMD )
Gaussian
ChemCraft
Ray

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.