Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties

Angewandte Chemie
David SchmidtFrank Würthner

Abstract

Unprecedented neutral perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) radicals and biradicals were synthesized by facile chemical oxidation of 4-hydroxyaryl-substituted PBIs. Subsequent characterization by optical and magnetic spectroscopic techniques, as well as quantum chemical calculations, revealed an open-shell singlet biradical ground state for the PBI biradical OS-2(..) (〈s(2)〉=1.2191) with a relatively small singlet-triplet energy gap of 0.041 eV and a large singlet biradical character of y=0.72.

References

Feb 6, 2003·Angewandte Chemie·Hans Henning WenkWolfram Sander
Jul 21, 2004·Chemical Communications : Chem Comm·Frank Würthner
Dec 13, 2006·Physical Review Letters·Young-Woo SonSteven G Louie
Mar 28, 2007·Angewandte Chemie·Kenji KamadaMasayoshi Nakano
Jun 24, 2009·Angewandte Chemie·Akihiro ShimizuTakashi Kubo
Nov 9, 2010·Chemical Reviews·Millicent B Smith, Josef Michl
Feb 23, 2011·The Journal of Physical Chemistry. a·Mark A IronBoris Rybtchinski
Jul 16, 2011·Journal of the American Chemical Society·Zhe SunJishan Wu
Sep 29, 2011·Angewandte Chemie·Mei-Jin LinFrank Würthner
Jan 10, 2012·Advanced Materials·Chen Li, Henrike Wonneberger
Jun 16, 2012·Journal of the American Chemical Society·Daniel T ChaseMichael M Haley
Aug 23, 2012·Journal of the American Chemical Society·Yuan LiJishan Wu
Jul 26, 2013·Chemical Reviews·Manabu Abe
Jan 8, 2014·Organic Letters·Jing GaoZhaohui Wang
Jan 15, 2014·Organic Letters·Vladimir V RoznyatovskiyMichael R Wasielewski
Jul 30, 2014·Accounts of Chemical Research·Zhe SunJishan Wu
Nov 14, 2014·Angewandte Chemie·David SchmidtFrank Würthner
May 8, 2015·Journal of the American Chemical Society·Lei JiTodd B Marder

❮ Previous
Next ❯

Citations

Jan 13, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sangsu LeeDongho Kim
Oct 19, 2017·Topics in Current Chemistry·Akihito Konishi, Takashi Kubo
Feb 6, 2018·Chemistry : a European Journal·Wangdong ZengJishan Wu
Aug 11, 2017·Physical Chemistry Chemical Physics : PCCP·K WilmaR Hildner
Sep 1, 2017·Physical Chemistry Chemical Physics : PCCP·Congdi ShangYu Fang
Oct 19, 2017·Angewandte Chemie·Maude DesrochesJuan Casado
Oct 15, 2019·Chemistry : a European Journal·Min Ji KimDennis D Cao
Oct 10, 2019·Chemistry : a European Journal·Mushraf HussainMariangela Di Donato
Jan 9, 2020·Chemical Communications : Chem Comm·Wenxiang WangYonghao Zheng
Mar 20, 2020·Angewandte Chemie·Sebastian N IntorpUwe H F Bunz
Apr 4, 2017·Angewandte Chemie·Guangwu LiJishan Wu
Nov 17, 2017·Chemistry, an Asian Journal·Jiajing FengZhaohui Wang
Aug 10, 2018·Chemical Science·Julian MesselbergerDominik Munz
Apr 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fang MiaoJishan Wu
Feb 20, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Julia HeitmüllerTobias Brixner
Aug 16, 2018·The Journal of Organic Chemistry·Vikas SharmaApurba Lal Koner
Oct 22, 2020·The Journal of Physical Chemistry. B·Akitsu HironoTaku Hasobe

❮ 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.