We describe the regioselective complexation of a non-symmetric 5-bromovaleronitrile axle by a non-symmetric pillar[5]arene bearing different alkyl (methyl and pentyl) rims, forming an oriented interpenetrated complex with the directionality of CN@methyl rim and Br@pentyl rim.
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http://dx.doi.org/10.1039/c4cc00800f | DOI Listing |
RSC Adv
June 2024
Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology Asahi-ku Osaka 535-8585 Japan
Interlocked compounds such as rotaxanes and catenanes exhibit unique kinetic properties in response to external chemical or physical stimuli and are therefore expected to be applied to molecular machines and molecular sensors. To develop a novel rotaxane for this application, an isophthalamide macrocycle and a neutral phenanthroline axle were used. Stable pseudorotaxanes are known to be formed using hydrogen bonds and π-π interactions.
View Article and Find Full Text PDFChemistry
August 2021
CLAN-Center for Light Activated Nanostructures, Istituto ISOF-CNR, Via Gobetti 101, 40129, Bologna, Italy.
The development of artificial nanoscale motors that can use energy from a source to perform tasks requires systems capable of performing directionally controlled molecular movements and operating away from chemical equilibrium. Here, the design, synthesis and properties of pseudorotaxanes are described, in which a photon input triggers the unidirectional motion of a macrocyclic ring with respect to a non-symmetric molecular axle. The photoinduced energy ratcheting at the basis of the pumping mechanism is validated by measuring the relevant thermodynamic and kinetic parameters.
View Article and Find Full Text PDFChem Sci
November 2019
Institut für Chemie und Biochemie , Freie Universität Berlin, Takustr. 3 , 14195 Berlin , Germany . Email:
J Mol Graph Model
January 2020
Department of Chemistry, Savitribai Phule Pune University, Pune, 411007, India. Electronic address:
The present work illustrates regioselective binding of nonsymmetric axle BuX (X = F, Cl, Br, CN) and 5-bromovaleronitrile (BVN) to the non-symmetric methyl pentyl pillar[5]arene (MPP5). Theoretical calculations reveal that the guest encapsulation within MPP5 is spontaneous and the conformer showing X weakly bound to pentyl rim of MPP5 is favoured over its other conformer wherein it interacts with methyl rim of the host. The noncovalent interactions namely C-H---π, C-H---X and H-H prevail over C-H⋯O hydrogen bonding in the complexes of MPP5.
View Article and Find Full Text PDFDalton Trans
May 2019
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland.
[2]rotaxanes composed of a dibenzo-24-crown-8 wheel (DB24C8) and an axle containing two metal-complexing tetraazamacrocyclic units linked with a p-xylylene bridge, coordinating the same or different metal ions (Ni and/or Cu) are described. A symmetric di-Ni rotaxane crystallizes in the monoclinic P21/c space group with one rotaxane cation and four PF6- counterions in the asymmetric part of the unit cell. In the crystal, the cations and anions of the investigated compound form an intertwined 3D-framework with C-HF and C-Hπ intermolecular interactions.
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