4.4 Article

Characterization of a slippage stopper for the 1,2-bis(pyridinium)ethane-[24]crown-8 ether [2]pseudorotaxane motif

Journal

TETRAHEDRON
Volume 64, Issue 36, Pages 8423-8427

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.05.042

Keywords

-

Funding

  1. NSERC of Canada

Ask authors/readers for more resources

Comparison of 1,2-bis(pyridinium)ethane axles containing iso-nicotinate esters (R=ethyl, iso-propyl, cyclohexyl, cycloheptyl) as the pyridinium unit shows that the cyclohexyl group provides a stopper size that allows slippage to be used as a method for pseudorotaxane/rotaxane formation employing dibenzo-24-crown-8 ether (DB24C8) as the wheel. Rates of complexation and decomplexation were measured in a number of solvent systems and the kinetic and thermodynamic parameters associated with the process reported. (C) 2008 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Multidisciplinary

Ring-through-ring molecular shuttling in a saturated [3]rotaxane

Kelong Zhu, Giorgio Baggi, Stephen J. Loeb

NATURE CHEMISTRY (2018)

Article Chemistry, Organic

A pyridinium/anilinium [2]catenane that operates as an acid-base driven optical switch

Sarah J. Vella, Stephen J. Loeb

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

An Anionic Ring Locked into an Anionic Axle: A Metastable Rotaxane with Chemically Activated Electrostatic Stoppers

Rubi A. Luna-Ixmatlahua, Anayeli Carrasco-Ruiz, Ruy Cervantes, Alberto Vela, Jorge Tiburcio

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Multidisciplinary

Solvent and Steric Influences on Rotational Dynamics in Porphyrinic Metal-Organic Frameworks with Mechanically Interlocked Pillars

Pablo Martinez-Bulit, Christopher A. O'Keefe, Kelong Zhu, Robert W. Schurko, Stephen J. Loeb

CRYSTAL GROWTH & DESIGN (2019)

Article Chemistry, Physical

Structural Dynamics by NMR in the Solid State: II. The MOMD Perspective of the Dynamic Structure of Metal-Organic Frameworks Comprising Several Mobile Components

Eva Meirovitch, Zhichun Liang, Robert W. Schurko, Stephen J. Loeb, Jack H. Freed

Summary: The application of the microscopic-order-macroscopic-disorder (MOMD) approach for analyzing dynamic H-2 NMR lineshapes in metal-organic frameworks (MOFs) is described in this study. By comparing the experimental results of UiO-68-d(4) and UWDM-9-d(4), it is found that MOFs with different structures exhibit different dynamic characteristics, and the phenyl-d(4) dynamics is more isotropic in a more crowded environment.

JOURNAL OF PHYSICAL CHEMISTRY B (2022)

Article Chemistry, Multidisciplinary

An Operative Electrostatic Slipping Mechanism along Macrocycle Flexibility Accelerates Guest Sliding during pseudo-Rotaxane Formation

Aldo C. Catalan, Axel A. Loredo, Ruy Cervantes, Jorge Tiburcio

Summary: This research introduces the process of forming pseudo-rotaxane using an electrostatically assisted sliding method, explores the effect of different macrocyclic conformational flexibility on sliding rate, and demonstrates that larger cyclic molecules can be slid through by combining different factors.

CHEMISTRYOPEN (2022)

Article Chemistry, Multidisciplinary

A translationally active ligand based on a [2] rotaxane molecular shuttle with a 2,2'-bipyridyl core

Ayan Dhara, Anton Dmitrienko, Rahaf N. N. Hussein, Ariel Sotomayor, Benjamin H. H. Wilson, Stephen J. J. Loeb

Summary: A rigid H-shaped [2]rotaxane molecular shuttle was synthesized, which consists of an axle containing benzimidazole recognition sites and a central bipyridyl group interlocked with a 24-crown-8 wheel. The central bipy unit acts as a speed bump that raises the barrier to shuttling for the [2]rotaxane. Coordination of a PtCl2 moiety to the bipy unit creates a steric barrier to shuttling, while addition of Zn(II) ions allows shuttling to occur through a ligand exchange mechanism.

CHEMICAL SCIENCE (2023)

Article Chemistry, Organic

Correlated translational motions in pseudo-rotaxane complexes controlled by a single chemical stimulus

Naoko Kotera, Pilar Montellano, Aldo C. Catalan, Anayeli Carrasco-Ruiz, Ruy Cervantes, Jorge Tiburcio

Summary: Coordinated motions are crucial for the operation of molecular machines. This study introduces a method of modifying the energy curve by using a single stimulus, which describes the threading and shuttling of a ring along a linear molecule.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Dynamics of a [2]rotaxane wheel in a crystalline molecular solid

Giorgio Baggi, Benjamin H. Wilson, Ayan Dhara, Christopher A. O'Keefe, Robert W. Schurko, Stephen J. Loeb

Summary: An H-shaped [2]rotaxane composed of a bis(benzimidazole) axle and a 24-membered crown ether wheel with four trityl groups forms a highly crystalline material allowing large amplitude motion of the interlocked macrocycle, characterized using variable-temperature (VT) H-2 solid-state nuclear magnetic resonance (SSNMR).

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Translational dynamics of a non-degenerate molecular shuttle imbedded in a zirconium metal-organic framework

Benjamin H. Wilson, Louae M. Abdulla, Robert W. Schurko, Stephen J. Loeb

Summary: In this study, a new [2]rotaxane molecular shuttle linker based on the binding of a 24-crown-8 ether macrocycle at a benzimidazole recognition site was synthesised and characterised. The translational motion of the molecular shuttle was studied both in solution and in the solid state. Incorporation of mesitylene into the pores of UWDM-11 was found to significantly increase the barrier for thermally driven translation of the macrocycle.

CHEMICAL SCIENCE (2021)

Article Chemistry, Physical

Exploring the dynamics of Zr-based metal-organic frameworks containing mechanically interlocked molecular shuttles

Ghazale Gholami, Benjamin H. Wilson, Kelong Zhu, Christopher A. O'Keefe, Robert W. Schurko, Stephen J. Loeb

Summary: Two Zr(IV) metal-organic frameworks (MOFs) were studied, incorporating a new H-shaped tetracarboxylate linker with [2]rotaxane molecular shuttles. Solid-state NMR and solution NMR spectra confirmed the successful incorporation of the [2]rotaxanes, while the study found that the structure of the linker affects the shuttling rate of the macrocyclic ring.

FARADAY DISCUSSIONS (2021)

Article Chemistry, Organic

One-pot synthesis of porphyrin-based [5]rotaxanes

Pablo Martinez-Bulit, Benjamin H. Wilson, Stephen J. Loeb

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Threading-gated photochromism in [2]pseudorotaxanes

Giorgio Baggi, Lorenzo Casimiro, Massimo Baroncini, Serena Silvi, Alberto Credi, Stephen J. Loeb

CHEMICAL SCIENCE (2019)

Article Chemistry, Multidisciplinary

Rotationally Active Ligands: Dialing-Up Multiple Interlocked Co-Conformations for Silver(I) Coordination

Giorgio Baggi, Stephen J. Loeb

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

Optical Distinction between Slow and Fast Translational Motion in Degenerate Molecular Shuttles

V. Nicholas Vukotic, Kelong Zhu, Giorgio Baggi, Stephen J. Loeb

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Organic

Facile synthesis of quinoxaline catalyzed by iron-based carbon material in water

Fuying Zhu, Yamei Lin

Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.

TETRAHEDRON (2024)

Article Chemistry, Organic

Simple approach towards phosphorus-substituted spiro 1,3,4-thiadiazolines

Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova

Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.

TETRAHEDRON (2024)

Article Chemistry, Organic

Recent advances in the synthesis of 2-cyclopentenones

Jisna Jose, Thomas Mathew

Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.

TETRAHEDRON (2024)