Kazan Federal University Digital Repository

New amphiphilic imidazolium/benzimidazolium calix[4]arene derivatives: Synthesis, aggregation behavior and decoration of DPPC vesicles for suzuki coupling in aqueous media

Show simple item record

dc.contributor.author Burilov V.
dc.contributor.author Garipova R.
dc.contributor.author Sultanova E.
dc.contributor.author Mironova D.
dc.contributor.author Grigoryev I.
dc.contributor.author Solovieva S.
dc.contributor.author Antipin I.
dc.date.accessioned 2021-02-25T20:54:09Z
dc.date.available 2021-02-25T20:54:09Z
dc.date.issued 2020
dc.identifier.uri https://dspace.kpfu.ru/xmlui/handle/net/162592
dc.description.abstract © 2020 by the authors. Licensee MDPI, Basel, Switzerland. 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.
dc.subject Calix[4]arene
dc.subject DPPC vesicles
dc.subject Miyaura coupling
dc.subject NHC complex
dc.subject Suzuki
dc.title New amphiphilic imidazolium/benzimidazolium calix[4]arene derivatives: Synthesis, aggregation behavior and decoration of DPPC vesicles for suzuki coupling in aqueous media
dc.type Article
dc.relation.ispartofseries-issue 6
dc.relation.ispartofseries-volume 10
dc.collection Публикации сотрудников КФУ
dc.relation.startpage 1
dc.source.id SCOPUS-2020-10-6-SID85086336175


Files in this item

This item appears in the following Collection(s)

  • Публикации сотрудников КФУ Scopus [24551]
    Коллекция содержит публикации сотрудников Казанского федерального (до 2010 года Казанского государственного) университета, проиндексированные в БД Scopus, начиная с 1970г.

Show simple item record

Search DSpace


Advanced Search

Browse

My Account

Statistics