Dimeric (Oligomeric) Derivatives of Cyclodextrins as a New Class of Supramolecular Systems: Their Synthesis and Inclusion Complexes

Грачев, М. К.; Терехова, И. В.; Shipilov, D. A.; Kutyasheva, N. V.; Emelianova, E. Y.

doi:10.1134/s1068162020010021

Cited by 4 publications

(2 citation statements)

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“…[ 39a ] The vinylic peaks of H3 around 8.17 ppm owing to self‐inclusion and shielding effect. [ 41 ] After forming CD‐SP 4 inclusion complex, the vinylic peaks change to 6.17 ppm because self‐inclusion was disappeared. G2 was dissolved in DMSO, and two alkene Ha of G2 are in different position impacted on many factors such as electronic effect, shielding effect, solvation effect, and conjugation effect [ 43 ] (see Figure S6).…”

Section: Resultsmentioning

confidence: 99%

“…Secondly, bridged ethylenediamine‐2Ada (Guest 1, G1) and bridged‐maleic‐2Ada (Guest 2, G2) were obtained by amide condensation of ethylenediamine, amantadine and adamantane chloride, and maleic chloride under alkaline conditions, respectively. Host 1–3 (H1–H3) has been obtained by the method of Emelianova [ 41 ] and can be successfully confirmed by 1 H NMR (see Figures S1–S3). H3 has been characterized by MALDI‐TOF mass spectrometry (see Figure S4).…”

Section: Methodsmentioning

confidence: 93%

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Highly efficient catalytic performance on CuAAC reaction by polymer‐like supramolecular self‐assemblies‐Cu(I) in aqueous solution

Bin

Yang

Guo

et al. 2022

Applied Organom Chemis

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A series of AA/BB types of cyclodextrin‐based supramolecular polymers (CD‐SP 1, 2, 3, and 4) have been constructed and characterized, which employed as ligands to accelerate the copper(I)‐catalyzed azide alkyne cycloaddition (CuAAC) using the conventional Sharpless–Fokin catalyst (CuSO4 + Na ascorbate) for the first time. Among them, the bridged‐maleic‐2‐β‐CD (CD = cyclodextrin)@bridged‐maleic‐2‐Ada (Ada = adamantane) (CD‐SP 4) self‐assembly shows more effective catalytic activity for CuAAC of azide and acetylene at 40 mol ppm of Cu(I) in water with excellent yields and remarkable TON (turnover number) values (up to 23,750). CD‐SP 4 can be fully recycled, and the catalyst can be reused efficiently for 10 times with negligible loss of catalyst activity. Therefore, it may extend the potential applications of cyclodextrin‐based supramolecular polymers in green chemical synthesis.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 93%