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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)466-472
Number of pages7
JournalSupramolecular Chemistry
Volume31
Issue number7
DOIs
Publication statusPublished - 3 Jul 2019

Cite this

Cameron, Lee ; Rajagopalan, Aswin ; Galan, Laura Abad ; Phe, Rene Z. H. ; Skelton, Brian W. ; Massi, Massimiliano ; Ogden, Mark I. / Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone. In: Supramolecular Chemistry. 2019 ; Vol. 31, No. 7. pp. 466-472.
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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].",
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Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone. / Cameron, Lee; Rajagopalan, Aswin; Galan, Laura Abad; Phe, Rene Z. H.; Skelton, Brian W.; Massi, Massimiliano; Ogden, Mark I.

In: Supramolecular Chemistry, Vol. 31, No. 7, 03.07.2019, p. 466-472.

Research output: Contribution to journalArticle

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

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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

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