New oxacalix[4]arene carboxylate detects viologen in protic media

Anna Peterson; Mari Liis Ludvig; Jevgenija Martõnova; Sandra Kaabel; Paul Kerner; Merle Uudsemaa; Aleksander Trummal; Maria Fomitšenko; Tõnis Pehk; Riina Aav; Jasper Adamson

doi:10.1080/10610278.2019.1659269

New oxacalix[4]arene carboxylate detects viologen in protic media

Anna Peterson, Mari Liis Ludvig, Jevgenija Martõnova, Sandra Kaabel, Paul Kerner, Merle Uudsemaa, Aleksander Trummal, Maria Fomitšenko, Tõnis Pehk, Riina Aav, Jasper Adamson^*

^*Corresponding author for this work

Not published at Aalto University

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

4 Citations (Scopus)

Abstract

We demonstrate that Ullman fragment-coupling can be used to synthesise an oxacalix[4]arene monocarboxylic acid, which provides easy access to its water-soluble carboxylato derivatives. Crystallographic and computational data suggest that the new carboxyl-substituted oxacalix[4]arene adopts a 1,3-alternate conformation both in the solid-state and in methanol solution. Its water-soluble tetrabutylammonium derivate can detect the herbicide paraquat at neutral pH in aqueous media (K _a = 111 ± 3 M^–1) and in methanol (K _a = 2020 ± 70 M^–1).

Original language	English
Pages (from-to)	313-319
Number of pages	7
Journal	Supramolecular Chemistry
Volume	32
Issue number	5
DOIs	https://doi.org/10.1080/10610278.2019.1659269
Publication status	Published - 3 May 2020
MoE publication type	A1 Journal article-refereed

Keywords

1,3-alternate conformation
herbicide sensing
Oxacalix[4]arene carboxylate

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10.1080/10610278.2019.1659269

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abstract = "We demonstrate that Ullman fragment-coupling can be used to synthesise an oxacalix[4]arene monocarboxylic acid, which provides easy access to its water-soluble carboxylato derivatives. Crystallographic and computational data suggest that the new carboxyl-substituted oxacalix[4]arene adopts a 1,3-alternate conformation both in the solid-state and in methanol solution. Its water-soluble tetrabutylammonium derivate can detect the herbicide paraquat at neutral pH in aqueous media (K a = 111 ± 3 M–1) and in methanol (K a = 2020 ± 70 M–1).",

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T1 - New oxacalix[4]arene carboxylate detects viologen in protic media

AU - Peterson, Anna

AU - Ludvig, Mari Liis

AU - Martõnova, Jevgenija

AU - Kaabel, Sandra

AU - Kerner, Paul

AU - Uudsemaa, Merle

AU - Trummal, Aleksander

AU - Fomitšenko, Maria

AU - Pehk, Tõnis

AU - Aav, Riina

AU - Adamson, Jasper

PY - 2020/5/3

Y1 - 2020/5/3

N2 - We demonstrate that Ullman fragment-coupling can be used to synthesise an oxacalix[4]arene monocarboxylic acid, which provides easy access to its water-soluble carboxylato derivatives. Crystallographic and computational data suggest that the new carboxyl-substituted oxacalix[4]arene adopts a 1,3-alternate conformation both in the solid-state and in methanol solution. Its water-soluble tetrabutylammonium derivate can detect the herbicide paraquat at neutral pH in aqueous media (K a = 111 ± 3 M–1) and in methanol (K a = 2020 ± 70 M–1).

AB - We demonstrate that Ullman fragment-coupling can be used to synthesise an oxacalix[4]arene monocarboxylic acid, which provides easy access to its water-soluble carboxylato derivatives. Crystallographic and computational data suggest that the new carboxyl-substituted oxacalix[4]arene adopts a 1,3-alternate conformation both in the solid-state and in methanol solution. Its water-soluble tetrabutylammonium derivate can detect the herbicide paraquat at neutral pH in aqueous media (K a = 111 ± 3 M–1) and in methanol (K a = 2020 ± 70 M–1).

KW - 1,3-alternate conformation

KW - herbicide sensing

KW - Oxacalix[4]arene carboxylate

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DO - 10.1080/10610278.2019.1659269

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SN - 1061-0278

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SP - 313

EP - 319

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

IS - 5

ER -

New oxacalix[4]arene carboxylate detects viologen in protic media

Abstract

Keywords

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