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

Overview

Journal Nanomaterials (Basel)

Date 2020 Jun 14

PMID 32532131

Citations 6

Authors

Vladimir Burilov

Ramilya Garipova

Elsa Sultanova

Diana Mironova

Ilya Grigoryev

Svetlana Solovieva

Igor Antipin

Affiliations

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Abstract

In this study, new types of amphiphilic calix[4]arene derivatives bearing -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 -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) were found to be active in Suzuki-Miyaura coupling of 1-bromo-4-nitrobenzene with phenylboronic acid in water. It was shown that bulky -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 -heterocyclic carbene (NHC) complex with methylimidazolium headgroups into DPPC vesicles enhances its catalytic activity in Suzuki-Miyaura coupling.

Citing Articles

New Carboxytriazolyl Amphiphilic Derivatives of Calix[4]arenes: Aggregation and Use in CuAAC Catalysis.

Mironova D, Bogdanov I, Akhatova A, Sultanova E, Garipova R, Khannanov A Int J Mol Sci. 2023; 24(23).

PMID: 38068985 PMC: 10706699. DOI: 10.3390/ijms242316663.

Novel pyrene-calix[4]arene derivatives as highly sensitive sensors for nucleotides, DNA and RNA.

Niksic-Franjic I, Colasson B, Reinaud O, Visnjevac A, Piantanida I, Saftic D RSC Adv. 2023; 13(39):27423-27433.

PMID: 37711378 PMC: 10498358. DOI: 10.1039/d3ra05696a.

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.

Burilov V, Garipova R, Mironova D, Sultanova E, Bogdanov I, Ocherednyuk E RSC Adv. 2022; 11(1):584-591.

PMID: 35423062 PMC: 8690898. DOI: 10.1039/d0ra09740c.

Design of Micro- and Nanoparticles: Self-Assembly and Application.

Padnya P, Stoikov I Nanomaterials (Basel). 2022; 12(3).

PMID: 35159775 PMC: 8839509. DOI: 10.3390/nano12030430.

NHC Polymeric Particles Obtained by Self-Assembly and Click Approach of Calix[4]Arene Amphiphiles as Support for Catalytically Active Pd Nanoclusters.

Burilov V, Mironova D, Sultanova E, Garipova R, Evtugyn V, Solovieva S Molecules. 2021; 26(22).

PMID: 34833956 PMC: 8625650. DOI: 10.3390/molecules26226864.

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