Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone

Lee Cameron; Aswin Rajagopalan; Laura Abad Galan; Rene Z. H. Phe; Brian W. Skelton; Massimiliano Massi; Mark I. Ogden

doi:10.1080/10610278.2019.1625357

Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone

Lee Cameron
, Aswin Rajagopalan
, Laura Abad Galan
, Rene Z. H. Phe
, Brian W. Skelton
, Massimiliano Massi
, Mark I. Ogden

School of Molecular Sciences

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

1 Citation (Scopus)

Abstract

The tetrazole-functionalised calixdiquinone 5,17-di-tert-butyl-26,28-bis-(1H-tetrazole-5-ylmethoxy)-calix[4]-25,27-diquinone Q was synthesised by chemical oxidation of the bis-tetrazole calix[4]arene precursor using PbO2/HClO4. The single crystal X-ray structure determination of Q confirmed the structure and showed binding of a water molecule in the solid state. Chemical reduction of Q to the dihydroquinone QR was achieved using N,N-diethylhydroxylamine. Comparison of the solution phase photophysical properties of Q or QR in the presence of terbium ions showed significant excitation only with QR, suggesting redox switching of the photophysical response may be possible with this or similar receptor.

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Original language	English
Pages (from-to)	466-472
Number of pages	7
Journal	Supramolecular Chemistry
Volume	31
Issue number	7
DOIs	https://doi.org/10.1080/10610278.2019.1625357
Publication status	Published - 3 Jul 2019

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title = "Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone",

abstract = "The tetrazole-functionalised calixdiquinone 5,17-di-tert-butyl-26,28-bis-(1H-tetrazole-5-ylmethoxy)-calix[4]-25,27-diquinone Q was synthesised by chemical oxidation of the bis-tetrazole calix[4]arene precursor using PbO2/HClO4. The single crystal X-ray structure determination of Q confirmed the structure and showed binding of a water molecule in the solid state. Chemical reduction of Q to the dihydroquinone QR was achieved using N,N-diethylhydroxylamine. Comparison of the solution phase photophysical properties of Q or QR in the presence of terbium ions showed significant excitation only with QR, suggesting redox switching of the photophysical response may be possible with this or similar receptor.[GRAPHICS].",

keywords = "Calixarene, lanthanide, quinone, ION-PAIR RECOGNITION, OXIDATION",

author = "Lee Cameron and Aswin Rajagopalan and Galan, \{Laura Abad\} and Phe, \{Rene Z. H.\} and Skelton, \{Brian W.\} and Massimiliano Massi and Ogden, \{Mark I.\}",

year = "2019",

month = jul,

day = "3",

doi = "10.1080/10610278.2019.1625357",

language = "English",

volume = "31",

pages = "466--472",

journal = "Supramolecular Chemistry",

issn = "1061-0278",

publisher = "Taylor \& Francis",

number = "7",

}

TY - JOUR

T1 - Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone

AU - Cameron, Lee

AU - Rajagopalan, Aswin

AU - Galan, Laura Abad

AU - Phe, Rene Z. H.

AU - Skelton, Brian W.

AU - Massi, Massimiliano

AU - Ogden, Mark I.

PY - 2019/7/3

Y1 - 2019/7/3

N2 - The tetrazole-functionalised calixdiquinone 5,17-di-tert-butyl-26,28-bis-(1H-tetrazole-5-ylmethoxy)-calix[4]-25,27-diquinone Q was synthesised by chemical oxidation of the bis-tetrazole calix[4]arene precursor using PbO2/HClO4. The single crystal X-ray structure determination of Q confirmed the structure and showed binding of a water molecule in the solid state. Chemical reduction of Q to the dihydroquinone QR was achieved using N,N-diethylhydroxylamine. Comparison of the solution phase photophysical properties of Q or QR in the presence of terbium ions showed significant excitation only with QR, suggesting redox switching of the photophysical response may be possible with this or similar receptor.[GRAPHICS].

AB - The tetrazole-functionalised calixdiquinone 5,17-di-tert-butyl-26,28-bis-(1H-tetrazole-5-ylmethoxy)-calix[4]-25,27-diquinone Q was synthesised by chemical oxidation of the bis-tetrazole calix[4]arene precursor using PbO2/HClO4. The single crystal X-ray structure determination of Q confirmed the structure and showed binding of a water molecule in the solid state. Chemical reduction of Q to the dihydroquinone QR was achieved using N,N-diethylhydroxylamine. Comparison of the solution phase photophysical properties of Q or QR in the presence of terbium ions showed significant excitation only with QR, suggesting redox switching of the photophysical response may be possible with this or similar receptor.[GRAPHICS].

KW - Calixarene

KW - lanthanide

KW - quinone

KW - ION-PAIR RECOGNITION

KW - OXIDATION

U2 - 10.1080/10610278.2019.1625357

DO - 10.1080/10610278.2019.1625357

M3 - Article

SN - 1061-0278

VL - 31

SP - 466

EP - 472

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

IS - 7

ER -

Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone

Abstract

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