Supramolecular and core–shell materials from self-assembled fibers

Balland-Longeau, A.; Mazabraud, Philippe; Duchêne, Alain; Thibonnet, J.

doi:10.1039/b917279c

Cited by 4 publications

(4 citation statements)

References 23 publications

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“…Consequently, the spatial steric hindrance from the more substituted aromatic side arms could potentially influence the complexation of the cyclophane with Ag + ions. However, as previously reported, ,,− the X-ray crystal structures of the ligands alone exhibit an unfavorable chair conformation for coordination to metal ions, regardless of the side arm. The chair conformation remains consistent with all tetra-armed cyclens reported thus far.…”

Section: Resultssupporting

confidence: 70%

Regioselective Coordination toward Silver(I) Ions by Bis- and Tris(Tetra-Armed Cyclen)s via Differential Electron Density of Aromatic Side Arms

et al. 2023

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Four types of bis-and tris(tetra-armed cyclen)s were prepared. 2 MF is a bis(tetra-armed cyclen) with electron-rich side arms (three 4-methoxybenzyl groups) and electron-deficient side arms (three 3,5-difluorobenzyl groups), connected by a 4,4′dimethyl-1,1′-biphenyl moiety. 3 MFM is a tris(tetra-armed cyclen) with 4-methoxybenzyl and 3,5-difluorobenzyl groups introduced on both ends and the central cyclen, respectively. 4 MFM is a Vshaped analogue of 3 MFM . 3 FMF is a tris(tetra-armed cyclen) where the aromatic side arms at both ends and the central cyclen of 3 MFM are exchanged. The regioselective coordination of silver(I) ions by these ligands is reported. Initially, we added Ag + ions to a compound (2 MF ) that consists of tetra-armed cyclen with 4methoxybenzyl groups as an electron-donating substituent on the aromatic rings and 3,5-difluorobenzyl groups as an electronwithdrawing substituent. 1 H NMR and 19 F{ 1 H} NMR spectroscopy exhibited that the cyclen with the 4-methoxybenzyl groups formed a complex with Ag + ions first, followed by the cyclen with the 3,5-difluorobenzyl groups. Next, we employed a compound (3 MFM ) with three cyclen units, where the cyclen at each end was functionalized with three 4-methoxybenzyl groups, and the central cyclen was functionalized with two 3,5-difluorobenzyl groups. Upon adding Ag + ions, we observed that the cyclen units at both ends formed complexes with Ag + ions initially, followed by the central cyclen forming a complex with Ag + ions. When we used 4 MFM , which is a V-shaped compound, the Ag + -induced-1 H NMR chemical shift changes are almost the same results as the 3 MFM . Furthermore, we synthesized a compound (3 FMF ) by interchanging the substituents on the cyclen units at the ends and the center. Interestingly, the order of the complex formation was reversed in this compound. These results demonstrated that tuning the electron density on the aromatic side arms through substituents makes it possible to achieve regioselective coordination with Ag + ions in bis-or tris(tetra-armed cyclen)s.

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Section: Resultssupporting

confidence: 70%

Regioselective Coordination toward Silver(I) Ions by Bis- and Tris(Tetra-Armed Cyclen)s via Differential Electron Density of Aromatic Side Arms

et al. 2023

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“…27 The interaction of L with an aqueous solution of fluorosilicic acid resulted in the mixed-anionic salt with the composition [H 3 L][F] [SiF 6 ]$4H 2 O (1), whose crystal structure was determined by single crystal X-ray diffraction. The conformation of the heterocycle and the arrangement of the aromatic substituents in L are very similar to those found in 1,4,7,10-tetrakis(4-nitrobenzyl)-1,4,7,10-tetraazacyclododecane 26 and 1,4,7,10-tetrakis(4-vinylbenzyl)-1,4,7,10-tetraazacyclododecane.…”

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confidence: 99%

“…The conformation of the heterocycle and the arrangement of the aromatic substituents in L are very similar to those found in 1,4,7,10-tetrakis(4-nitrobenzyl)-1,4,7,10-tetraazacyclododecane 26 and 1,4,7,10-tetrakis(4-vinylbenzyl)-1,4,7,10-tetraazacyclododecane. 27 The interaction of L with an aqueous solution of fluorosilicic acid resulted in the mixed-anionic salt with the composition [H 3 L][F] [SiF 6 ]$4H 2 O (1), whose crystal structure was determined by single crystal X-ray diffraction. The compound 1 crystallizes in the monoclinic C2/c space group with one formula unit in the asymmetric unit.…”

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confidence: 99%

Tetrabenzylcyclen as a receptor for fluoride

Gelmboldt

Ganin

Basok³

et al. 2011

CrystEngComm

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A tetraazacyclic ligand, tetrabenzylcyclen (L), was synthesized using an improved method with a higher yield by treatment of cyclen with benzylchloride in the presence of potassium carbonate. The reaction of L with an aqueous solution of fluorosilicic acid yielded a mixed-anionic salt with the composition [H 3 L][F][SiF 6 ]$4H 2 O (1). The single crystal X-ray study revealed that the macrocyclic trication essentially changes the conformation compared to the free ligand in order to tightly accommodate the fluoride inside and to keep the hexafluorosilicate anions and water molecules outside in the solid state complex.

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“…The increasing polymer numbers indicate the increasing VAc-content (decreasing Cou45-content) of the samples. 172 N-(3-aminopropyl) methacrylamide, poly(ethylene glycol) methacrylate (PEGMA) and BIS, [178][179][180] 2-hydroxyethyl acrylate and PEG 575 diacrylate, 181 as well as DVB, 182 as label for fluorescence microscopy imaging. Additionally, Hwang could show that fluorescent, polyacrylic acid coated magnetic nanodiamonds could be ingested into HeLa cells.…”

Section: Fluoresceinmentioning

confidence: 99%

Fluorescent monomers as building blocks for dye labeled polymers: synthesis and application in energy conversion, biolabeling and sensors

2013

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This review focuses on side-chain functionalized polymers derived from direct (co)polymerization of fluorescent dyes. This overview about polymerizable dyes includes 1,8-naphthalimides, fluoresceins, rhodamines, coumarins, azo-dyes, oxadiazoles, diverse aromatic dyes as well as selected other dyes that cannot be classified within these groups. The discussed dyes have been functionalized with a polymerizable unit in order to apply straight-forward polymerization procedures. Therefore, the center of attention is set to the optical properties of the polymerizable dyes and the applicable polymerization techniques. Furthermore, the various applications (i.e., in biomedicine and pharmacy, as thermo-responsive materials and energy transfer materials, for dispersion of carbon nanotubes and others) of each polymer are discussed.

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Supramolecular and core–shell materials from self-assembled fibers

Cited by 4 publications

References 23 publications

Regioselective Coordination toward Silver(I) Ions by Bis- and Tris(Tetra-Armed Cyclen)s via Differential Electron Density of Aromatic Side Arms

Regioselective Coordination toward Silver(I) Ions by Bis- and Tris(Tetra-Armed Cyclen)s via Differential Electron Density of Aromatic Side Arms

Tetrabenzylcyclen as a receptor for fluoride

Fluorescent monomers as building blocks for dye labeled polymers: synthesis and application in energy conversion, biolabeling and sensors

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