Complexation‐Induced Translational Isomerism: Shuttling through Stepwise Competitive Binding

Marlin, Dana S.; Cabrera, Diego Gonzàlez; Leigh, David A.; Slawin, Alexandra M. Z.

doi:10.1002/ange.200501761

Cited by 35 publications

(15 citation statements)

References 97 publications

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“…[84] Ligand 70 is based on the structure successfully used to assemble hydrogen bond-assembled benzylic amide catenanes and rotaxanes. [162] It is modified to incorporate a tridentate 2,6-diiminopyridine coordination motif that allows two distinct routes for the preparation of catenates. A kinetic template effect route utilizes formation of pre-catenate complex 39-M II .…”

Section: Trigonal Bipyramidal Geometriesmentioning

confidence: 99%

Strategies and Tactics for the Metal‐Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links

et al. 2011

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More than a quarter of a century after the first metal template synthesis of a [2]catenane in Strasbourg, there now exists a plethora of strategies available for the construction of mechanically bonded and entwined molecular level structures. Catenanes, rotaxanes, knots and Borromean rings have all been successfully accessed by methods in which metal ions play a pivotal role. Originally metal ions were used solely for their coordination chemistry; acting either to gather and position the building blocks such that subsequent reactions generated the interlocked products or by being an integral part of the rings or "stoppers" of the interlocked assembly. Recently the role of the metal has evolved to encompass catalysis: the metal ions not only organize the building blocks in an entwined or threaded arrangement but also actively promote the reaction that covalently captures the interlocked structure. This Review outlines the diverse strategies that currently exist for forming mechanically bonded molecular structures with metal ions and details the tactics that the chemist can utilize for creating cross-over points, maximizing the yield of interlocked over non-interlocked products, and the reactions-of-choice for the covalent capture of threaded and entwined intermediates.

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Section: Trigonal Bipyramidal Geometriesmentioning

confidence: 99%

Strategies and Tactics for the Metal‐Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links

et al. 2011

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“…A myriad of molecular machines were constructed and successfully operated by several external stimuli, such as light, [2] redox reactions, [3] pH changes, [4] and ions. [5] Porphyrin and its derivatives have exhibited their unique applications in organic materials and supramolecular chemistry. [6,7] Particularly, they were extensively studied in synthetic models of photosynthesis to mimic the functions of the light-harvesting antenna complexes and the photosynthetic reaction center in natural systems.…”

Section: Introductionmentioning

confidence: 99%

Energy Transfer and Concentration‐Dependent Conformational Modulation: A Porphyrin‐Containing [3]Rotaxane

Han

Pei

2012

Chemistry An Asian Journal

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A zinc porphyrin-containing [3]rotaxane A was synthesized through a copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Energy donors and acceptor porphyrin were introduced to dibenzo[24]crown-8 (DB24C8) and dibenzyl ammonium (DBA) units of [3]rotaxane A to understand the intramolecular energy transfer process. Investigations of the photophysical properties of [3]rotaxane A demonstrated that the intramolecular efficient energy transfer readily occurred from the donors on the wheels to the porphyrin center on the axis. The fluorescence of energy donors in the region of 400 to 450 nm was efficiently absorbed by the porphyrin acceptor under irradiation at 345 nm, and finally a red light emission at about 600 nm was achieved. Further investigation indicated that the conformation of [3]rotaxane A was self-modulated by changing its concentration in CH(2)Cl(2). The triazole groups on the wheel coordinated or uncoordinated to Zn(2+) through intramolecular self-coordination with the change in the concentration of [3]rotaxane A in CH(2)Cl(2). Therefore, this conformational change was reversible in a non-coordinating solvent such as CH(2)Cl(2) but inhibited in a coordinating solvent such as THF. Such interesting behaviors were rarely observed in porphyrin derivatives. This self-modulation feature opens up the possibility of controlling molecular conformation by varying concentration.

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“…Fullerene stoppers have also been introduced in rotaxanes as a way to probe the motion of the ring as a consequence of their well‐defined photophysical43 and electrochemical properties 44. 45 Leigh‐like rotaxanes are particularly attractive for this purpose because 1) shuttling and pirouetting can be achieved through a wide variety of stimulus, such as light,4, 13, 14, 46, 47 electrons,4, 7 solvent change,9, 10, 48, 49 temperature,46, 47 pH variation,12 electric field,50 coordination,51, 52 and chemically,53 and 2) they are not built from chromophores or redox groups and are therefore the perfect backbones for studying the effect of submolecular motion on photo‐ and electroactive components. A good example is molecular shuttle 1 ,9 in which some selected photophysical properties of the fullerene were applied to detect the position of the macrocycle along the thread (Scheme ).…”

Section: Probing Molecular Motion Through the Properties Of C60mentioning

confidence: 99%

Fullerenes: Multitask Components in Molecular Machinery

et al. 2007

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Molecular machines are molecular-scale devices that carry out predetermined tasks derived from molecular motion. This Minireview illustrates how fullerenes can be used as multitask building blocks in molecular machinery, providing new perspectives for fullerenes. Indeed, C(60) can be applied as a photo- and electroactive stopper owing to its size, as a probe for molecular motion as a result of its well-defined physicochemical properties, and to induce motion through pi-pi interactions. Such molecular motion can be employed to modulate light-driven electron-transfer events, extending the potential applications of molecular machines to the typical fields of application of fullerenes.

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Complexation‐Induced Translational Isomerism: Shuttling through Stepwise Competitive Binding

Cited by 35 publications

References 97 publications

Strategies and Tactics for the Metal‐Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links

Strategies and Tactics for the Metal‐Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links

Energy Transfer and Concentration‐Dependent Conformational Modulation: A Porphyrin‐Containing [3]Rotaxane

Fullerenes: Multitask Components in Molecular Machinery

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