Synthesis, structure and catalysis/applications of N-heterocyclic carbene based on macrocycles

Yang, Jun; Liu, Jiaqi; Wang, Yaofang; Wang, Junwen

doi:10.1007/s10847-017-0766-9

Cited by 21 publications

(8 citation statements)

References 93 publications

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“…However, for the best of our knowledge there are no examples of NHC-catalytic systems made by preliminary supramolecular assembly of NHC ligand monomers with their subsequent covalent xation, which nevertheless has a great advantage in the formation of functional nanomaterials with controlled morphology. NHC-complexes on the calix [4]arene scaffold attracts a great attention 18 since it is possible to anchor one or more NHC fragments at one molecular platform, which plays role both as bulky ligand and molecular cavity contribute to catalytic transformations. Recently we demonstrated that amphiphilic Pd(II) bis-NHC complexes on the thiacalix [4]arene backbone 19 or in situ made Pd(II) bis-NHC complexes on the calix [4]arene backbone 20 can be successfully used in coupling and hydrogenation reactions, performed in organic or water media.…”

Section: Introductionmentioning

confidence: 99%

New poly-imidazolium–triazole particles by CuAAC cross-linking of calix[4]arene bis-azide/alkyne amphiphiles – a prospective support for Pd in the Mizoroki–Heck reaction

et al. 2021

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Section: Introductionmentioning

confidence: 99%

New poly-imidazolium–triazole particles by CuAAC cross-linking of calix[4]arene bis-azide/alkyne amphiphiles – a prospective support for Pd in the Mizoroki–Heck reaction

et al. 2021

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“…Recently, much attention has been paid to NHC complexes on the calixarene platform [ 12 ]. Embedding of NHC units on the calixarene scaffold can serve as a tool to change the environment of central metal due to steric hindrance and electronic effects.…”

Section: Introductionmentioning

confidence: 99%

New Amphiphilic Imidazolium/Benzimidazolium Calix[4]arene Derivatives: Synthesis, Aggregation Behavior and Decoration of DPPC Vesicles for Suzuki Coupling in Aqueous Media

et al. 2020

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In this study, new types of amphiphilic calix[4]arene derivatives bearing N-alkyl/aryl imidazolium/benzimidazolium fragments were designed and synthesized by two step transformation: Regioselective Blanc chloromethylation of distal-di-O-butyl calix[4]arene and subsequent interaction with N-Substituted imidazole/benzimidazole. Critical aggregation concentration (CAC) values were estimated using pyrene fluorescent probe. Obtained macrocycles were found to form submicron particles with electrokinetic potential +44–+57 mV in aqueous solution. For the first time it was found that amphiphilic calixarene causes the fast transformation of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) multilamellar vesicles into unilamellar ones and leads to the ordering of the lipid in membranes at the molar calixarene/DPPC ratio more than 0.07. In situ complexes of calixarene aggregates with Pd(OAc)2 were found to be active in Suzuki–Miyaura coupling of 1-bromo-4-nitrobenzene with phenylboronic acid in water. It was shown that bulky N-substituents of heterocycle decrease the catalytic activity of the aggregates. These result can be assigned to the inhibition effect of Pd(II) complex in situ formation by bulky substituents located on the aggregate surface. Embedding of the most active palladium N-heterocyclic carbene (NHC) complex with methylimidazolium headgroups into DPPC vesicles enhances its catalytic activity in Suzuki–Miyaura coupling.

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“…Porphyrinoids and NHCs are relevant ligands in coordination and organometallic chemistry. As illustrated by the above discussion and other recent articles, [61] several molecular systems combining porphyrins and NHC ligands were reported during the last decade. Axial coordination of NHCs on metalloporphyrins was mainly investigated for applications in catalysis, but some compounds such as iridium(III) complexes appeared as promising candidates for dual therapy against cancer.…”

Section: Discussionmentioning

confidence: 61%

Molecular Systems Combining Porphyrinoids and N‐Heterocyclic Carbenes

et al. 2021

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Porphyrins and N‐heterocyclic carbenes (NHCs) are both relevant ligands in the fields of coordination and organometallic chemistry. Despite evident structural differences, porphyrins and NHCs have a lot in common such as their ability to form strong metal‐ligand bonds and their use in catalysis, materials science and biomedicine. During the last decade, several molecular systems combining porphyrins and NHC ligands were reported in the literature. The present review gathers relevant examples where NHC ligands are either axially bonded to metalloporphyrins or covalently attached to the porphyrin cores. Structural diversity, electronic interplay between porphyrins and NHCs and some relevant applications in catalysis and biomedicine are notably described. Finally, molecular systems combining NHCs with other original porphyrinoids such as N‐confused porphyrins, subporphyrins and norcorroles are also presented.

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Synthesis, structure and catalysis/applications of N-heterocyclic carbene based on macrocycles

Cited by 21 publications

References 93 publications

New poly-imidazolium–triazole particles by CuAAC cross-linking of calix[4]arene bis-azide/alkyne amphiphiles – a prospective support for Pd in the Mizoroki–Heck reaction

New poly-imidazolium–triazole particles by CuAAC cross-linking of calix[4]arene bis-azide/alkyne amphiphiles – a prospective support for Pd in the Mizoroki–Heck reaction

New Amphiphilic Imidazolium/Benzimidazolium Calix[4]arene Derivatives: Synthesis, Aggregation Behavior and Decoration of DPPC Vesicles for Suzuki Coupling in Aqueous Media

Molecular Systems Combining Porphyrinoids and N‐Heterocyclic Carbenes

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