Monitoring self-sorting by electrospray ionization mass spectrometry: formation intermediates and error-correction during the self-assembly of multiply threaded pseudorotaxanes

Journal of the American Chemical Society
Wei JiangChristoph A Schalley

Abstract

Three binary pseudorotaxanes, which are based on two different secondary ammonium/crown ether binding motifs, have been studied by (1)H NMR and (1)H,(1)H EXSY NMR experiments with respect to their thermodynamic stabilities and their axle exchange kinetics. The stability ranking does not follow the order of axle exchange rates, and the thermodynamically most stable axle-wheel combinations assemble only slowly. On the basis of these binding motifs, a series of self-sorting systems have been studied ranging from simple four-component mixtures through sequence-specific pseudorotaxanes to multiply threaded complexes. Because of the mismatch of kinetic and thermodynamic order, wrongly assembled structures are unavoidable, which require error-correction steps to yield the final thermodynamically controlled self-sorted products. These error-correction steps can easily be monitored by electrospray mass spectrometry, when a mixed-flow microreactor is coupled to the ion source to cover second time scales. Self-assembly intermediates, wrongly assembled structures, and the final thermodynamic products can be simultaneously identified. The determination of preferred assembly pathways as well as the formation of dead-end structures provides a...Continue Reading

References

Dec 26, 2001·Chemical Reviews·S LeiningerP J Stang
Aug 5, 1997·Chemical Reviews·M. Morgan Conn, Julius Rebek
Mar 30, 2002·Science·Jean-Marie Lehn
Mar 30, 2002·Science·George M Whitesides, Bartosz Grzybowski
Apr 4, 2002·Proceedings of the National Academy of Sciences of the United States of America·Jean-Marie Lehn
Apr 12, 2002·Mass Spectrometry Reviews·C A Schalley
Apr 18, 2002·Proceedings of the National Academy of Sciences of the United States of America·Thomas CliffordDaryle H Busch
Nov 20, 2002·Accounts of Chemical Research·S Russell Seidel, Peter J Stang
Apr 17, 2003·Journal of the American Chemical Society·Anxin Wu, Lyle Isaacs
Jun 5, 2003·Journal of the American Chemical Society·Jason W Jones, Harry W Gibson
Feb 26, 2004·Journal of the American Chemical Society·Jovica D BadjićJ Fraser Stoddart
Mar 10, 2004·Chemistry : a European Journal·Christoph A SchalleyMarkus Albrecht
Mar 18, 2004·Chemical Society Reviews·Frank WürthnerChantu R Saha-Möller
May 6, 2004·Journal of the American Chemical Society·César MárquezWerner M Nau
May 29, 2004·Science·Kelly S ChichakJ Fraser Stoddart
Sep 11, 2004·The Journal of Organic Chemistry·Pritam MukhopadhyayLyle Isaacs
Sep 17, 2004·Chemistry : a European Journal·Avril R WilliamsDavid J Williams
Jan 19, 2005·Accounts of Chemical Research·Stuart J CantrillJ Fraser Stoddart
Apr 14, 2005·Chemical Reviews·J Christopher LoveGeorge M Whitesides
Apr 20, 2005·Accounts of Chemical Research·Makoto FujitaBruno Therrien
Jul 5, 2005·Science·Robert F Service
Jul 21, 2005·Journal of the American Chemical Society·Markus AlbrechtRoland Fröhlich
Nov 10, 2005·Journal of the American Chemical Society·Simin LiuLyle Isaacs
Mar 30, 2006·Journal of the American Chemical Society·Stefan A PelsterFerdi Schüth
Jul 21, 2006·Organic & Biomolecular Chemistry·Bilge BaytekinChristoph A Schalley
Sep 14, 2006·Chemical Reviews·Peter T CorbettSijbren Otto
Oct 26, 2006·Journal of the American Chemical Society·Pritam MukhopadhyayLyle Isaacs
Dec 19, 2006·Chemical Society Reviews·Shannon M Biros, Julius Rebek
May 16, 2007·Organic Letters·Sriparna ChakrabartiLyle Isaacs
Dec 25, 2007·The Journal of Organic Chemistry·Damien BraekersJean F Desreux
Jan 17, 2008·Chemical Society Reviews·R Frederick Ludlow, Sijbren Otto
Jan 29, 2008·Journal of the American Chemical Society·Elizabeth S BarrettJulius Rebek
Feb 22, 2008·Rapid Communications in Mass Spectrometry : RCM·Leonardo Silva Santos, Jürgen O Metzger
Mar 11, 2008·Journal of the American Chemical Society·Marius V CâmpianDavid Williamson
May 9, 2008·Chemical Communications : Chem Comm·Mikhail V RekharskyYoshihisa Inoue
May 30, 2008·Accounts of Chemical Research·Praveen Kumar Vemula, George John
Jul 1, 2008·The Journal of Organic Chemistry·Soumyadip GhoshLyle Isaacs
Sep 27, 2008·Journal of the American Chemical Society·Wei JiangChristoph A Schalley
Oct 1, 2008·Journal of the American Chemical Society·Hiroshi ItoEiji Yashima

❮ Previous
Next ❯

Citations

Aug 19, 2011·Chemical Reviews·Marina M Safont-SempereFrank Würthner
Apr 27, 2011·Inorganic Chemistry·Amber M Johnson, Richard J Hooley
Feb 16, 2011·Chemical Communications : Chem Comm·Subrata SahaPradyut Ghosh
Jun 15, 2010·Journal of Mass Spectrometry : JMS·Wei Jiang, Christoph A Schalley
Apr 5, 2016·Journal of Mass Spectrometry : JMS·Karol NowosinskiChristoph A Schalley
Aug 16, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lucas A Powers, David B Smithrud
Sep 8, 2016·Angewandte Chemie·Edward A Neal, Stephen M Goldup
Sep 8, 2016·Chemistry : a European Journal·Zheng MengChuan-Feng Chen
Aug 27, 2014·Chemistry : a European Journal·Xiaocun LuGeorge R Newkome
May 2, 2015·Chemical Communications : Chem Comm·Mirko LohseStefan Hecht
Jul 1, 2017·Journal of the American Chemical Society·Chang-Bo HuangHai-Bo Yang
Jul 12, 2017·Organic Letters·Chuan GaoHe Tian
Jun 25, 2014·Chemical Society Reviews·Zhenhui QiChristoph A Schalley
Jul 23, 2016·Chemical Communications : Chem Comm·Bin HuaFeihe Huang
Jul 6, 2018·Chemical Communications : Chem Comm·Dan WuGuocan Yu
Jan 3, 2014·Chemistry : a European Journal·Koushik Acharyya, Partha Sarathi Mukherjee
Sep 13, 2014·Chemistry : a European Journal·Inmaculada AngurellMarianne Engeser
Oct 12, 2010·Organic & Biomolecular Chemistry·Antonella FontanaDomenico Spinelli
Sep 22, 2011·Angewandte Chemie·Zhi-Jun ZhangYu Liu
May 1, 2012·Organic & Biomolecular Chemistry·Manik Lal Saha, Michael Schmittel
Nov 28, 2013·Organic & Biomolecular Chemistry·Zhenhui QiChristoph A Schalley
Jul 1, 2015·Beilstein Journal of Organic Chemistry·Mirko LohseStefan Hecht
Mar 17, 2012·Beilstein Journal of Organic Chemistry·Nora L LöwChristoph A Schalley
Jan 11, 2020·ChemistryOpen·Heather M CoubroughAndrew J Wilson
May 13, 2020·Angewandte Chemie·Jessica GroppiAlberto Credi
Sep 6, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Julia Barreira-FontechaVickie McKee
Aug 14, 2013·Chemical Communications : Chem Comm·Xiaodong ChiFeihe Huang

❮ 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

Chemical Communications : Chem Comm
Michael Schmittel, Kingsuk Mahata
Journal of the American Chemical Society
Jovica D BadjićJ Fraser Stoddart
Journal of the American Chemical Society
Tomoya OshikiriAkira Harada
© 2021 Meta ULC. All rights reserved