Helicate, macrocycle, or catenate: Dynamic topological control over subcomponent self-assembly

Chemistry : a European Journal
Marie HutinJonathan R Nitschke

Abstract

The aqueous reaction between equimolar amounts of 2-(2-(2-aminoethoxy)ethoxy)ethanamine, 1,10-phenanthroline-2,9-dialdehyde and copper(I) produced a dimeric helical macrocycle in quantitative yield. This ring could also be generated by the addition of two equivalents of the diamine to an acyclic helicate containing four mono-imine residues: A transimination occurred, the chelate effect being implicated as a driving force. In the case of a helicate containing mono-imines derived from anilines, the substitution of diamine for monoamine was reversible upon lowering the pH. The aliphatic diamine was protonated at a higher pH than the arylamine, which left the arylamine free for incorporation instead of the alkyl diamine. This reaction thus opened the possibility of switching between closed macrocyclic and open helicate topologies by changing the pH. An additional closed topology became accessible through the use of a diamine that incorporates two rigid phenylene spacer groups between a flexible chain and the imine-forming nitrogen atoms. The resulting catenate consists of a pair of topologically interlinked macrocycles. The presence of the phenylene groups appeared to dictate the topology of the final product, making the formation ...Continue Reading

References

Nov 25, 2000·Angewandte Chemie·V BalzaniJ F Stoddart
Jun 20, 2001·Accounts of Chemical Research·J F Stoddart
Oct 25, 2001·The Journal of Organic Chemistry·Marcus WeckRobert H. Grubbs
Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
Oct 1, 2003·Proceedings of the National Academy of Sciences of the United States of America·Jonathan R Nitschke, Jean-Marie Lehn
May 8, 2004·Molecular Microbiology·Olivier Espeli, Kenneth J Marians
May 29, 2004·Science·Kelly S ChichakJ Fraser Stoddart
May 29, 2004·Science·Leyong WangVolker Böhmer
Sep 17, 2004·Chemistry : a European Journal·Christoph A SchalleyFritz Vögtle
Nov 26, 2004·Journal of the American Chemical Society·Mark R SambrookAndrew R Cowley
Nov 30, 2004·Science·José V HernándezDavid A Leigh
Dec 14, 2004·Angewandte Chemie·Jonathan R NitschkeGérald Bernardinelli
Dec 17, 2004·Journal of the American Chemical Society·Jonathan R NitschkeDavid Gérard
Mar 17, 2005·Chemical Communications : Chem Comm·Jean-Pierre Sauvage
Jul 6, 2005·Chemical Communications : Chem Comm·Andrea J PetersJ Fraser Stoddart
Aug 3, 2005·Proceedings of the National Academy of Sciences of the United States of America·David Schultz, Jonathan R Nitschke
Aug 30, 2005·Nature Materials·José BernáFrancesco Zerbetto
Apr 17, 2001·Angewandte Chemie·David A LeighJenny K Y Wong

❮ Previous
Next ❯

Citations

Aug 11, 2006·Organic Letters·Raphael M Bennes, Douglas Philp
Dec 16, 2011·Nature Chemistry·Jean-François AymeDavid Schultz
May 12, 2015·Angewandte Chemie·Jonathon E BevesIñigo J Vitorica-Yrezabal
Sep 17, 2013·Chemistry : a European Journal·Hana BunzenErkki Kolehmainen
Dec 10, 2014·Chemistry : a European Journal·Eva M López-VidalJosé M Quintela
Jan 1, 2014·Angewandte Chemie·Jesús MosqueraJonathan R Nitschke
Jan 25, 2007·Chemistry : a European Journal·David Schultz, Jonathan R Nitschke
Mar 21, 2007·Angewandte Chemie·Gennady V OshovskyWillem Verboom
Apr 5, 2008·Chemistry : a European Journal·Marie HutinJonathan R Nitschke
Jul 16, 2008·Angewandte Chemie·Stephen M GoldupAlexandra M Z Slawin
Mar 24, 2009·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Philip C Haussmann, J Fraser Stoddart
Jul 10, 2009·Chemical Society Reviews·James D CrowleyRoy T McBurney
Nov 14, 2006·Proceedings of the National Academy of Sciences of the United States of America·Marie HutinJonathan R Nitschke
Jul 15, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Boris BrusilowskijChristoph A Schalley
Mar 17, 2012·Beilstein Journal of Organic Chemistry·Nora L LöwChristoph A Schalley
Jan 30, 2020·Chemistry : a European Journal·Masahide TominagaKentaro Yamaguchi
Apr 23, 2013·Angewandte Chemie·Samuel P BlackJeremy K M Sanders
Dec 22, 2009·Organic & Biomolecular Chemistry·Ken Cham-Fai LeungJ Fraser Stoddart
Jan 5, 2013·Chemical Communications : Chem Comm·Tanya K RonsonJonathan R Nitschke
May 8, 2013·Angewandte Chemie·Jonathon E BevesRobin G Pritchard
May 8, 2015·Angewandte Chemie·Guzmán Gil-RamírezAlexander J Stephens
Mar 13, 2008·Science and Technology of Advanced Materials·Katsuhiko ArigaSomobrata Acharya
May 26, 2018·Chemical Society Reviews·E M G JamiesonS M Goldup
Jul 17, 2012·Chemical Society Reviews·Michael D Ward, Paul R Raithby
Oct 15, 2014·Angewandte Chemie·Christopher J CampbellSteffen L Woltering
Aug 30, 2008·Angewandte Chemie·Prasenjit MalJonathan R Nitschke
Mar 29, 2014·Chemical Society Reviews·Nicholas H Evans, Paul D Beer
May 25, 2012·Chemical Communications : Chem Comm·Paul D NewmanBenson M Kariuki
Apr 21, 2018·Chemical Science·Kenji CapriceFabien B L Cougnon
Dec 19, 2020·Chemical Communications : Chem Comm·Christopher J SerpellPaul D Beer
Dec 9, 2009·Journal of the American Chemical Society·Stephen M GoldupAlexandra M Z Slawin
Feb 23, 2010·Journal of the American Chemical Society·Julien LeclaireGérard Buono
Mar 5, 2010·Journal of the American Chemical Society·Maryline BeylerJean-Pierre Sauvage
Mar 12, 2009·Journal of the American Chemical Society·David A LeighD Barney Walker
Oct 10, 2013·Journal of the American Chemical Society·Revital KaminkerMilko E van der Boom
Apr 17, 2015·Chemical Reviews·Anna J McConnellJonathan R Nitschke
May 8, 2013·The Journal of Organic Chemistry·Hajime IwamotoTakeharu Haino
Feb 10, 2011·The Journal of Organic Chemistry·Ho Yu Au-YeungJeremy K M Sanders

❮ Previous
Next ❯

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.