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A modular approach for the synthesis of nanometer-sized polynitroxide multi-spin systems

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Silvia Valera, James E Taylor, David S B Daniels, Daniel M Dawson, Kasun S Athukorala Arachchige, Sharon E Ashbrook, Alexandra M Z Slawin, Bela E Bode

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Abstract

The synthesis of rigid symmetric polyradical model systems with inter-spin distances between 1.4 and 4 nm and their room temperature continuous wave (CW) EPR spectra are reported. Conditions for attachment of the spin-label via esterification have been optimized on the direct synthesis of polyradicals from commercially available polyphenols and the carboxylic acid functionalized nitroxide TPC. A common synthetic protocol utilizing 4-hydroxy-4′-iodobiphenyl as a key building block has been used to synthesize an equilateral biradical and a triradical in only two steps from commercially available starting materials. The first synthesis of a tetraradical based upon an adamantane core bearing six equivalent nitroxide–nitroxide distances is also reported. These systems are very promising candidates for studying multi-spin effects in pulsed EPR distance measurements.
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Original languageEnglish
Pages (from-to)8313–8323
Number of pages11
JournalJournal of Organic Chemistry
Volume79
Issue number17
Early online date7 Aug 2014
DOIs
Publication statusPublished - 20 Aug 2014

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