Upper-Rim Monofunctionalisation in the Synthesis of Triazole- and Disulfide-Linked Multicalix[4]- and -[6]arenes

William H. Gardiner; Matthew Camilleri; Luis A. Martinez-Lozano; Sean P. 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 H. Gardiner, Matthew Camilleri, Luis A. Martinez-Lozano, Sean P. Bew, G. Richard Stephenson

University of East Anglia

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

5 Citations (SciVal)

Abstract

Covalently linked multiple calixarenes are valued in supramolecular chemistry. This work reports 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 and hexahydroxy 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	9
Journal	Chemistry - A European Journal
Volume	24
Issue number	71
Early online date	26 Nov 2018
DOIs	https://doi.org/10.1002/chem.201804755
Publication status	Published - 17 Dec 2018

Funding

The authors acknowledge financial support from the EU Inter-reg IV Manche/Channel cross-border projects IS:CE-chem (4061) and AIcc (4196) and the EPSRC Mass Spectrometry Service at the University of Swansea for HRMS measurements and for their help and advice.

Keywords

amino acids
calixarenes
multi-calixarenes
peptidocalixarene
selective alkylation
supramolecular chemistry

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201804755

https://ueaeprints.uea.ac.uk/68734/

Cite this

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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. This work reports 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 and hexahydroxy 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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author = "Gardiner, \{William H.\} and Matthew Camilleri and Martinez-Lozano, \{Luis A.\} and Bew, \{Sean P.\} and Stephenson, \{G. Richard\}",

year = "2018",

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doi = "10.1002/chem.201804755",

language = "English",

volume = "24",

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journal = "Chemistry - A European Journal",

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publisher = "John Wiley and Sons Inc.",

number = "71",

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T1 - Upper-Rim Monofunctionalisation in the Synthesis of Triazole- and Disulfide-Linked Multicalix[4]- and -[6]arenes

AU - Gardiner, William H.

AU - Camilleri, Matthew

AU - Martinez-Lozano, Luis A.

AU - Bew, Sean P.

AU - Stephenson, G. Richard

PY - 2018/12/17

Y1 - 2018/12/17

N2 - Covalently linked multiple calixarenes are valued in supramolecular chemistry. This work reports 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 and hexahydroxy 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. This work reports 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 and hexahydroxy 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.

KW - amino acids

KW - calixarenes

KW - multi-calixarenes

KW - peptidocalixarene

KW - selective alkylation

KW - supramolecular chemistry

UR - https://www.scopus.com/pages/publications/85057875181

U2 - 10.1002/chem.201804755

DO - 10.1002/chem.201804755

M3 - Article

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AN - SCOPUS:85057875181

SN - 0947-6539

VL - 24

SP - 19089

EP - 19097

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 71

ER -

Upper-Rim Monofunctionalisation in the Synthesis of Triazole- and Disulfide-Linked Multicalix[4]- and -[6]arenes

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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