Remote Photoregulated Ring Gliding in a [2]Rotaxane via a Molecular Effector

Tron, Arnaud; Pianet, Isabelle; Martínez-Cuezva, Alberto; Tucker, James H. R.; Pisciottani, Luca; Alajarı́n, Mateo; Berná, José; McClenaghan, Nathan D.

doi:10.1021/acs.orglett.6b03457

Cited by 27 publications

(19 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Shuttling along the full length of the rotaxane axle could be restored by addition of Hamilton‐type receptors (e.g. 59 in Figure b) that competitively sequester barbital , …”

Section: Progress In Hydrogen Bond Templated Rotaxanes and Catenanesmentioning

confidence: 99%

Recent Advances in the Synthesis and Application of Hydrogen Bond Templated Rotaxanes and Catenanes

Evans

2019

Eur J Org Chem

View full text Add to dashboard Cite

Alongside the use of metal cations and π–π stacking, hydrogen bonding is one of the major templating interactions used to prepare rotaxanes and catenanes. In this review, a brief summary of key historical milestones will be followed by discussion of developments from over the last decade in both synthetic methodology and application of hydrogen bond templated interlocked molecules. Hydrogen bond templation can allow for rapid access to interlocked molecules in high yields, with select examples having been put to useful purpose, in applications such as organocatalysis and cellular imaging.

show abstract

“…Shuttling along the full length of the rotaxane axle could be restored by addition of Hamilton‐type receptors (e.g. 59 in Figure b) that competitively sequester barbital , …”

Section: Progress In Hydrogen Bond Templated Rotaxanes and Catenanesmentioning

confidence: 99%

Recent Advances in the Synthesis and Application of Hydrogen Bond Templated Rotaxanes and Catenanes

Evans

2019

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…The release of a hydrogen‐bonded molecule from a photoactivatable system was used by McClenaghan and Berna and co‐workers in 2017 to control the translational movement in a [2]rotaxane (see Figure ) . The release of a barbiturate messenger from a hydrogen‐bonding receptor ( 20 ) is effectuated by the [4+4] photocycloaddition of anthracene moieties.…”

Section: Chemical Concatenation With Other Speciesmentioning

confidence: 99%

“…[50][51][52][53] The release of ahydrogen-bonded molecule from aphotoactivatable system wasu sed by McClenaghana nd Berna and coworkers in 2017 to controlt he translational movement in a [ 2]rotaxane( see Figure 8). [54] The release of ab arbiturate messenger from ah ydrogen-bonding receptor (20)i se ffectuated by the [4+ +4] photocycloaddition of anthracene moieties. The barbiturate can then occupy hydrogen-bonding stations on the thread of the [2]rotaxane (21), which modulates the wheel gliding.…”

Section: Chemical Concatenation With Other Speciesmentioning

confidence: 99%

Chemical Communication between Molecules

Remón

Pischel

2017

ChemPhysChem

View full text Add to dashboard Cite

In this Minireview conceptual approaches towards the communication between (supra)molecular species are illustrated. The reviewed mechanisms include photophysical communication through energy transfer and communication mediated by chemical species that are released from precursors upon application of an external stimulus. The focus is on the stimulation by (reversible) photoreactions. Special attention has been given to supramolecular systems that illustrate the idea of chemical communication and information transfer in a very descriptive manner.

show abstract

“…The study of mechanically interlocked molecules, such as catenanes, [1] knots, [2] and rotaxanes, [3] has enormously propelled progress in the field of molecular machines, [4] with control of shuttling motion [5] in rotaxanes and catenanes representing prominent highlights. [6] Use of remote control, [7] i. e., control via chemical signal transfer [8] from a remote relay, for operating the shuttling motion is yet unknown.…”

Section: Introductionmentioning

confidence: 99%

Remote Control of the Synthesis of a [2]Rotaxane and its Shuttling via Metal‐Ion Translocation

et al. 2019

View full text Add to dashboard Cite

This paper is dedicated to Prof. Jean-Marie Lehn on the occasion of his 80th birthday with deep gratitude for his inspiring and groundbreaking work.Remote control in an eight-component network commanded both the synthesis and shuttling of a [2]rotaxane via metal-ion translocation, the latter being easily monitored by distinct colorimetric and fluorimetric signals. Addition of zinc(II) ions to the red colored copper-ion relay station rapidly liberated copper(I) ions and afforded the corresponding zinc complex that was visualized by a bright sky blue fluorescence at 460 nm. In a mixture of all eight components of the network, the liberated copper(I) ions were translocated to a macrocycle that catalyzed formation of a rotaxane by a double-click reaction of acetylenic and diazide compounds. The shuttling frequency in the copper-loaded [2]rotaxane was determined to k 298 = 30 kHz (ΔH � = 62.3 � 0.6 kJ mol À 1 , ΔS � = 50.1 � 5.1 J mol À 1 K À 1 , ΔG � 298 = 47.4 kJ mol À 1 ). Removal of zinc(II) ions from the mixture reversed the system back generating the metal-free rotaxane. Further alternate addition and removal of Zn 2 + reversibly controlled the shuttling mode of the rotaxane in this eight-component network where the ion translocation status was monitored by the naked eye.[a] I.

show abstract

Remote Photoregulated Ring Gliding in a [2]Rotaxane via a Molecular Effector

Cited by 27 publications

References 33 publications

Recent Advances in the Synthesis and Application of Hydrogen Bond Templated Rotaxanes and Catenanes

Recent Advances in the Synthesis and Application of Hydrogen Bond Templated Rotaxanes and Catenanes

Chemical Communication between Molecules

Remote Control of the Synthesis of a [2]Rotaxane and its Shuttling via Metal‐Ion Translocation

Contact Info

Product

Resources

About