Upper-rim monofunctionalisation in the synthesis of triazole- and disulfide-linked multicalix[4]- and -[6]arenes

William Gardiner; Matthew Camilleri; Luis Angel Martinez Lozano; Sean Bew; G. Richard Stephenson

doi:10.1002/chem.201804755

Upper-rim monofunctionalisation in the synthesis of triazole- and disulfide-linked multicalix[4]- and -[6]arenes

William Gardiner, Matthew Camilleri, Luis Angel Martinez Lozano, Sean Bew, G. Richard Stephenson

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

28 Downloads (Pure)

Abstract

Covalently linked multiple calixarenes are valued in supramolecular chemistry. We report an easy and versatile synthetic route to covalently linked double and triple calix[4]arene and calix[6]arenes by a novel DMF‐controlled selective alkylation of a convenient and readily available upper‐rim dimethylaminomethyl‐substituted tetrahydroxy calix[4]arene and ‐[6]arenes. Synthetic routes to upper‐rim functionalised redox active disulfide‐linked double‐, tetra‐ and peptidohybrid‐calixarenes employing either redox chemistry (CH₂SH) or thiolates (CH₂S^–) are also opened up from the same key starting material.

Original language	English
Pages (from-to)	19089-19097
Number of pages	10
Journal	Chemistry - A European Journal
Volume	24
Issue number	71
Early online date	16 Oct 2018
DOIs	https://doi.org/10.1002/chem.201804755
Publication status	Published - 17 Dec 2018

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10.1002/chem.201804755

Accepted manuscriptAccepted author manuscript, 1.58 MBLicence: CC BY-NC

http://doi.wiley.com/10.1002/chem.201804755

Sean Bew
- S.Bewuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Associate Professor in Chemistry
- Chemistry of Materials and Catalysis - Member
Person: Research Group Member, Academic, Teaching & Research
G.Richard Stephenson
- G.R.Stephensonuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Emeritus Professor
- Chemistry of Materials and Catalysis - Member
Person: Honorary, Research Group Member

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title = "Upper-rim monofunctionalisation in the synthesis of triazole- and disulfide-linked multicalix[4]- and -[6]arenes",

abstract = "Covalently linked multiple calixarenes are valued in supramolecular chemistry. We report an easy and versatile synthetic route to covalently linked double and triple calix[4]arene and calix[6]arenes by a novel DMF‐controlled selective alkylation of a convenient and readily available upper‐rim dimethylaminomethyl‐substituted tetrahydroxy calix[4]arene and ‐[6]arenes. Synthetic routes to upper‐rim functionalised redox active disulfide‐linked double‐, tetra‐ and peptidohybrid‐calixarenes employing either redox chemistry (CH2SH) or thiolates (CH2S–) are also opened up from the same key starting material.",

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year = "2018",

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T1 - Upper-rim monofunctionalisation in the synthesis of triazole- and disulfide-linked multicalix[4]- and -[6]arenes

AU - Gardiner, William

AU - Camilleri, Matthew

AU - Martinez Lozano, Luis Angel

AU - Bew, Sean

AU - Stephenson, G. Richard

PY - 2018/12/17

Y1 - 2018/12/17

N2 - Covalently linked multiple calixarenes are valued in supramolecular chemistry. We report an easy and versatile synthetic route to covalently linked double and triple calix[4]arene and calix[6]arenes by a novel DMF‐controlled selective alkylation of a convenient and readily available upper‐rim dimethylaminomethyl‐substituted tetrahydroxy calix[4]arene and ‐[6]arenes. Synthetic routes to upper‐rim functionalised redox active disulfide‐linked double‐, tetra‐ and peptidohybrid‐calixarenes employing either redox chemistry (CH2SH) or thiolates (CH2S–) are also opened up from the same key starting material.

AB - Covalently linked multiple calixarenes are valued in supramolecular chemistry. We report an easy and versatile synthetic route to covalently linked double and triple calix[4]arene and calix[6]arenes by a novel DMF‐controlled selective alkylation of a convenient and readily available upper‐rim dimethylaminomethyl‐substituted tetrahydroxy calix[4]arene and ‐[6]arenes. Synthetic routes to upper‐rim functionalised redox active disulfide‐linked double‐, tetra‐ and peptidohybrid‐calixarenes employing either redox chemistry (CH2SH) or thiolates (CH2S–) are also opened up from the same key starting material.

U2 - 10.1002/chem.201804755

DO - 10.1002/chem.201804755

M3 - Article

VL - 24

SP - 19089

EP - 19097

JO - Chemistry-A European Journal

JF - Chemistry-A European Journal

SN - 0947-6539

IS - 71

ER -

Upper-rim monofunctionalisation in the synthesis of triazole- and disulfide-linked multicalix[4]- and -[6]arenes

Abstract

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Sean Bew

G.Richard Stephenson

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