Direct Synthesis of an Unprecedented Stable Radical of Nickel(II) 3,5-Bis(dimedonyl)azadiisoindomethene with Strong and Narrow Near-Infrared Absorption at λ ∼ 1000 nm

Inorganic Chemistry
Elena A MakarovaVictor N Nemykin

Abstract

An unprecedented stable neutral radical nickel(II) complex of 3,5-bis(dimedonyl)azadiisoindomethene (1) was prepared by the direct reaction between 1,3-diiminoisoindoline and dimedone. A new radical complex 1 has an intense and narrow absorption at 1008 nm and can be reduced to a less stable anionic [1]-with a typical aza(dibenzo)boron dipyrromethene (aza-BODIPY) UV-vis spectrum. Complex 1, along with two other colored condensation reaction products 2 and 3, was characterized by spectroscopy and X-ray crystallography, while the paramagnetic nature of 1 was probed by EPR and SQUID methods. Complex 1 forms dimers in the solid state with short (∼3.16 Å) Ni---Ni contacts. Redox data on 1 are indicative of a reversible reduction process in this complex; its magnetism suggests a S =1/2state with the spin density delocalized over the aza-BODIPY core. The experimental data 1 and [1]-were correlated with the density functional theory (DFT) and time-dependent DFT calculations.

References

Sep 26, 2002·Chemical Communications : Chem Comm·John KilloranDonal F O'Shea
Aug 26, 2004·Journal of the American Chemical Society·Aoife GormanDonal F O'Shea
Jul 2, 2005·The Journal of Organic Chemistry·Michael J HallDonal F O'Shea
Jul 17, 2007·Inorganic Chemistry·Thomas S TeetsThomas G Gray
Sep 21, 2007·Organic Letters·Marta LirasFrancisco Amat-Guerri
Oct 11, 2007·Chemical Reviews·Aurore Loudet, Kevin Burgess
Dec 20, 2007·Angewandte Chemie·Gilles UlrichAnthony Harriman
Sep 26, 2008·Organic Letters·Aurore LoudetDonal F O'Shea
Sep 10, 2009·Chemistry : a European Journal·Raymond ZiesselAnthony Harriman
Feb 4, 2011·Chemistry : a European Journal·Roland GresserMoritz Riede
Mar 8, 2011·Chemistry, an Asian Journal·Hua LuNagao Kobayashi
Jul 29, 2011·Chemical Society Reviews·Noël BoensWim Dehaen
Sep 26, 2012·The Journal of Organic Chemistry·Marco GrossiDonal F O'Shea
Sep 28, 2012·Chemical Society Reviews·Anyanee KamkaewKevin Burgess
Apr 15, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·F Thomas

❮ Previous
Next ❯

Citations

May 29, 2020·Chemical Communications : Chem Comm·Briana R SchrageChristopher J Ziegler

❮ Previous
Next ❯

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.