Literature DB >> 25951013

Catenanes: fifty years of molecular links.

Guzmán Gil-Ramírez1, David A Leigh2, Alexander J Stephens1.   

Abstract

Half a century after Schill and Lüttringhaus carried out the first directed synthesis of a [2]catenane, a plethora of strategies now exist for the construction of molecular Hopf links (singly interlocked rings), the simplest type of catenane. The precision and effectiveness with which suitable templates and/or noncovalent interactions can arrange building blocks has also enabled the synthesis of intricate and often beautiful higher order interlocked systems, including Solomon links, Borromean rings, and a Star of David catenane. This Review outlines the diverse strategies that exist for synthesizing catenanes in the 21st century and examines their emerging applications and the challenges that still exist for the synthesis of more complex topologies.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  catenanes; interlocked molecules; links; supramolecular chemistry; template synthesis

Year:  2015        PMID: 25951013      PMCID: PMC4515087          DOI: 10.1002/anie.201411619

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  135 in total

1.  Topologically linked protein rings in the bacteriophage HK97 capsid.

Authors:  W R Wikoff; L Liljas; R L Duda; H Tsuruta; R W Hendrix; J E Johnson
Journal:  Science       Date:  2000-09-22       Impact factor: 47.728

2.  Benzylic Imine Catenates: Readily Accessible Octahedral Analogues of the Sauvage Catenates This work was supported by the EPSRC. D.A.L. is an EPSRC Advanced Research Fellow (AF/982324). We thank Dr. B. P. Murphy (Manchester Metropolitan University) for useful discussions and Drs. T. J. Kidd, S. M. Lacy (University of Warwick), G. Di Orazio and R. Nasreen (University of Manchester, Institute of Science and Technology) for early ligand design.

Authors:  David A. Leigh; Paul J. Lusby; Simon J. Teat; Andrew J. Wilson; Jenny K. Y. Wong
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-17       Impact factor: 15.336

3.  Simultaneous self-assembly of a [2]catenane, a trefoil knot, and a Solomon link from a simple pair of ligands.

Authors:  Thirumurugan Prakasam; Matteo Lusi; Mourad Elhabiri; Carlos Platas-Iglesias; John-Carl Olsen; Zouhair Asfari; Sarah Cianférani-Sanglier; François Debaene; Loïc J Charbonnière; Ali Trabolsi
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

4.  Self-assembly of a giant molecular Solomon link from 30 subcomponents.

Authors:  Clément Schouwey; Julian J Holstein; Rosario Scopelliti; Konstantin O Zhurov; Konstantin O Nagornov; Yury O Tsybin; Oliver S Smart; Gérard Bricogne; Kay Severin
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-28       Impact factor: 15.336

5.  A shape-persistent quadruply interlocked giant cage catenane with two distinct pores in the solid state.

Authors:  Gang Zhang; Oliver Presly; Fraser White; Iris M Oppel; Michael Mastalerz
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-06       Impact factor: 15.336

6.  Synthesis of multi-1,10-phenanthroline ligands with 1,3-phenylene linkers and their lithium complexes.

Authors:  Christiane Dietrich-Buchecker; Benoît Colasson; Damien Jouvenot; Jean-Pierre Sauvage
Journal:  Chemistry       Date:  2005-07-18       Impact factor: 5.236

7.  A radically configurable six-state compound.

Authors:  Jonathan C Barnes; Albert C Fahrenbach; Dennis Cao; Scott M Dyar; Marco Frasconi; Marc A Giesener; Diego Benítez; Ekaterina Tkatchouk; Oleksandr Chernyashevskyy; Weon Ho Shin; Hao Li; Srinivasan Sampath; Charlotte L Stern; Amy A Sarjeant; Karel J Hartlieb; Zhichang Liu; Raanan Carmieli; Youssry Y Botros; Jang Wook Choi; Alexandra M Z Slawin; John B Ketterson; Michael R Wasielewski; William A Goddard; J Fraser Stoddart
Journal:  Science       Date:  2013-01-25       Impact factor: 47.728

8.  Synthesis of a [2]catenane around a Ru(diimine)3(2+) scaffold by ring-closing metathesis of olefins.

Authors:  Fabio Arico; Pierre Mobian; Jean-Marc Kern; Jean-Pierre Sauvage
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

9.  Multiple catenanes derived from calix[4]arenes.

Authors:  Leyong Wang; Myroslav O Vysotsky; Anca Bogdan; Michael Bolte; Volker Böhmer
Journal:  Science       Date:  2004-05-28       Impact factor: 47.728

10.  Tetrameric cyclic double helicates as a scaffold for a molecular Solomon link.

Authors:  Jonathon E Beves; Christopher J Campbell; David A Leigh; Robin G Pritchard
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-06       Impact factor: 15.336

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  44 in total

Review 1.  Artificial Molecular Machines.

Authors:  Sundus Erbas-Cakmak; David A Leigh; Charlie T McTernan; Alina L Nussbaumer
Journal:  Chem Rev       Date:  2015-09-08       Impact factor: 60.622

2.  Creating complex molecular topologies by configuring DNA four-way junctions.

Authors:  Di Liu; Gang Chen; Usman Akhter; Timothy M Cronin; Yossi Weizmann
Journal:  Nat Chem       Date:  2016-07-04       Impact factor: 24.427

3.  A Solomon link through an interwoven molecular grid.

Authors:  Jonathon E Beves; Jonathan J Danon; David A Leigh; Jean-François Lemonnier; Iñigo J Vitorica-Yrezabal
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-08       Impact factor: 15.336

4.  Self-Assembly of Catenanes from Lasso Peptides.

Authors:  Caitlin D Allen; A James Link
Journal:  J Am Chem Soc       Date:  2016-10-21       Impact factor: 15.419

Review 5.  BINOL as a chiral element in mechanically interlocked molecules.

Authors:  Matthias Krajnc; Jochen Niemeyer
Journal:  Beilstein J Org Chem       Date:  2022-05-06       Impact factor: 2.544

6.  Mixed valence mono- and hetero-metallic grid catenanes.

Authors:  Chandan Giri; Filip Topić; Massimo Cametti; Kari Rissanen
Journal:  Chem Sci       Date:  2015-06-30       Impact factor: 9.825

7.  Supramolecular polymerization of a ureidopyrimidinone-based [2]catenane prepared via ring-closing metathesis.

Authors:  Abraham J P Teunissen; José Augusto Berrocal; Christiaan H W A Corbet; E W Meijer
Journal:  J Polym Sci A Polym Chem       Date:  2017-07-03       Impact factor: 2.702

8.  Diastereoselective synthesis of [1]rotaxanes via an active metal template strategy.

Authors:  Noël Pairault; Adrien Bessaguet; Romain Barat; Lucas Frédéric; Grégory Pieters; Jeanne Crassous; Isabelle Opalinski; Sébastien Papot
Journal:  Chem Sci       Date:  2020-12-29       Impact factor: 9.825

9.  Spin-labelled mechanically interlocked molecules as models for the interpretation of biradical EPR spectra.

Authors:  Lorenzo Gualandi; Paola Franchi; Elisabetta Mezzina; Stephen M Goldup; Marco Lucarini
Journal:  Chem Sci       Date:  2021-05-14       Impact factor: 9.825

10.  Rise of the Molecular Machines.

Authors:  Euan R Kay; David A Leigh
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-27       Impact factor: 15.336

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