A [2]rotaxane capped by a beta-cyclodextrin and a 2,4,6-trinitrophenyl group has been prepared by dissolving 6-aminocinnamoyl beta-cyclodextrin in water with 1-adamantane carboxylic acid and complexation with alpha-cyclodextrin followed by the reaction with 2,4,6-trinitrobenzene sulfonic acid sodium salt. The [2]rotaxane has been found to form supramolecular polymers by host-guest interactions.
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Curved Nanographenes as Stoppers in a [2]Rotaxane with Two-Photon Excited Emission.
J Org Chem
July 2024
Departamento de Química Orgánica, Unidad de Excelencia de Química, Facultad de Ciencias, Universidad de Granada, Avda. Fuente Nueva s/n, 18071 Granada, Spain.
Heptagon-containing distorted nanographenes are used as stoppers for the capping of a [2]rotaxane through a Michael-type addition reaction to vinyl sulfone groups. These curved aromatics are bulky enough to prevent the disassembly of the rotaxane but also give emissive and nonlinear (two-photon absorption and emission) optical properties to the structure.
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Org Lett
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Departamento de Química and Centro de Investigaciones Científicas Avanzadas (CICA). Facultad de Ciencias, Universidade da Coruña, 15071 A Coruña, Spain.
The synthesis of new triphenylphosphonium-capped cucurbit[7]uril (CB[7])- and cucurbit[8]uril (CB[8])-based [2]rotaxanes was achieved by a simultaneous threading-capping strategy. While the use of CB[7] produced the designed [2]rotaxane, attempts to obtain the CB[8] analogue were unsuccessful due to the unexpected strong interaction found between the host and the phosphonium caps leading to pseudo-heteroternary host-guest complexes. This unusual binding motif has been extensively studied experimentally, with results in good agreement with those obtained by dispersion-corrected DFT methods.
View Article and Find Full Text PDFCyclodextrin-Based [c2]Daisy Chain Rotaxane Insulating Two Diarylacetylene Cores.
Chemistry
January 2021
Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka, 5648680, Japan.
A [c2]daisy chain rotaxane with two diarylacetylene cores was efficiently synthesized in 53 % yield by capping a C -symmetric pseudo[2]rotaxane composed of two diarylacetylene-substituted permethylated α-cyclodextrins (PM α-CDs) with aniline stoppers. The maximum absorption wavelength of the [c2]daisy chain rotaxane remained almost unchanged in various solvents, unlike that of the stoppered monomer, indicating that the two independent diarylacetylene cores were insulated from the external environment by the PM α-CDs. Furthermore, the [c2]daisy chain rotaxane exhibited fluorescence emission derived from both diarylacetylene monomers and the excimer, which implies that the [c2]daisy chain structure can undergo contraction and extension.
View Article and Find Full Text PDFAdjusting the Dynamism of Covalent Imine Chemistry in the Aqueous Synthesis of Cucurbit[7]uril-based [2]Rotaxanes.
Org Lett
November 2019
Departamento de Química and Centro de Investigaciones Científicas Avanzadas (CICA), Facultad de Ciencias , Universidade da Coruña , E-15071 A Coruña , Spain.
The self-assembly of [2]rotaxane has been achieved in aqueous media at pD 4 by the simultaneous threading into CB[7] of an appropriate axle ended with acyl hydrazine groups and its concurrent capping with two molecules of a triphenylphosphonium aldehyde as stoppers. The dynamism of the rotaxane has been demonstrated under acidic conditions and can be diminished by solvent swapping, pH modulation, or, surprisingly, the removal of the carbonyl groups on the axle.
View Article and Find Full Text PDF[2]Rotaxane End-Capping Synthesis by Click Michael-Type Addition to the Vinyl Sulfonyl Group.
Chemistry
April 2019
Departamento de Química Orgánica, Universidad de Granada, Facultad de Ciencias, Avda. Fuente Nueva, S/N, 18071, Granada, Spain.
We report the application of the click Michael-type addition reaction to vinyl sulfone or vinyl sulfonate groups in the synthesis of rotaxanes through the threading-and-capping method. This methodology has proven to be efficient and versatile as it allowed the preparation of rotaxanes using template approaches based on different noncovalent interactions (i.e.
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