High-Yielding Synthesis of Chiral Donor-Acceptor Catenanes

The Journal of Organic Chemistry
Mehrafarin Eilbigi DehkordiG Dan Pantoş

Abstract

We report the synthesis of [2]catenanes (Hopf links) in water utilizing disulfides and aromatic donor-acceptor interactions. The electron-rich dialkoxynaphthalene (DN) building blocks interact with electron-deficient naphthalenediimide (NDI) moieties connected by a polyamine chain. We study the effect of the polyamine linkers on the behavior of the library. The polyamine's length and the number of nitrogen atoms in the chain affect the library distribution, leading in some cases to the assembly of catenanes in up to 93% yield.

References

Jan 16, 2002·Drug Discovery Today·Sijbren OttoJeremy K M Sanders
Sep 14, 2006·Chemical Reviews·Peter T CorbettSijbren Otto
Nov 18, 2006·Angewandte Chemie·Cari D PentecostJ Fraser Stoddart
Jul 10, 2008·Organic Letters·Ali CoskunJ Fraser Stoddart
Jul 24, 2008·Journal of the American Chemical Society·Kevin R WestSijbren Otto
Jan 28, 2009·Proceedings of the National Academy of Sciences of the United States of America·Ho Yu Au-YeungJeremy K M Sanders
Oct 17, 2009·Journal of the American Chemical Society·Ho Yu Au-YeungJeremy K M Sanders
Oct 23, 2010·Chemistry : a European Journal·Cari D MeyerJ Fraser Stoddart
Oct 27, 2010·The Journal of Organic Chemistry·Paul M AlveyBrent L Iverson
Jan 5, 2011·Journal of the American Chemical Society·Lei FangJ Fraser Stoddart
Feb 17, 2011·Journal of the American Chemical Society·Fabien B L CougnonJeremy K M Sanders
Feb 18, 2011·Angewandte Chemie·Lei FangJ Fraser Stoddart
Mar 29, 2011·The Journal of Organic Chemistry·Koujiro TambaraG Dan Pantoş
Oct 7, 2011·Chemical Communications : Chem Comm·Megan M BoyleJean-Pierre Sauvage
Dec 31, 2011·Accounts of Chemical Research·Fabien B L Cougnon, Jeremy K M Sanders
Jan 4, 2012·Angewandte Chemie·Fabien B L CougnonJeremy K M Sanders
Sep 25, 2012·Journal of the American Chemical Society·Ross S ForganJ Fraser Stoddart
Oct 12, 2012·Organic & Biomolecular Chemistry·Miguel Á Alemán García, Nick Bampos
Nov 3, 2012·Journal of the American Chemical Society·Fabien B L CougnonJeremy K M Sanders
Nov 10, 2012·Science·Nandhini PonnuswamyJeremy K M Sanders
Jun 5, 2013·Journal of the American Chemical Society·Jianwei LiSijbren Otto
Oct 18, 2013·Chemical Society Reviews·Samuel P BlackArtur R Stefankiewicz
Mar 1, 2014·Chemical Communications : Chem Comm·Brian RasmussenMichael Pittelkow
May 17, 2014·Journal of the American Chemical Society·Nandhini PonnuswamyJeremy K M Sanders
Oct 25, 2014·Nature Chemistry·David A LeighAlexander J Stephens
Jan 15, 2015·Organic & Biomolecular Chemistry·Fabien B L CougnonJeremy K M Sanders
Mar 25, 2015·Nature Chemistry·Christopher S WoodJonathan R Nitschke
May 8, 2015·Angewandte Chemie·Guzmán Gil-RamírezAlexander J Stephens
May 12, 2015·Angewandte Chemie·Jonathon E BevesIñigo J Vitorica-Yrezabal
Aug 27, 2015·Angewandte Chemie·Yi-Wei WuSheng-Hsien Chiu
Nov 21, 2015·Nature Chemistry·Hao LiJonathan L Sessler
May 19, 2017·The Journal of Organic Chemistry·Ken ItoShinichi Saito
Apr 21, 2018·Chemical Science·Kenji CapriceFabien B L Cougnon

❮ Previous
Next ❯

Citations

Dec 19, 2018·Chemistry, an Asian Journal·Antony Wing Hung Ng, Ho Yu Au-Yeung
May 9, 2019·Chemical Communications : Chem Comm·Chi-Chung YeeHo Yu Au-Yeung
Jul 17, 2020·Nature Communications·Tiberiu-M Gianga, G Dan Pantoș
Jun 8, 2021·Chemical Science·Tiberiu-M GiangaG Dan Pantoş
Jan 9, 2022·Scientific Reports·Marcin Konopka, Artur R Stefankiewicz

❮ 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.

Related Papers

Organic & Biomolecular Chemistry
Fabien B L CougnonJeremy K M Sanders
Journal of the American Chemical Society
Fabien B L CougnonJeremy K M Sanders
Chemical Communications : Chem Comm
Giles M PrenticeG Dan Pantoş
© 2022 Meta ULC. All rights reserved