A modular approach for the synthesis of nanometer-sized polynitroxide multi-spin systems
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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.
Valera , S , Taylor , J E , Daniels , D S B , Dawson , D M , Athukorala Arachchige , K S , Ashbrook , S E , Slawin , A M Z & Bode , B E 2014 , ' A modular approach for the synthesis of nanometer-sized polynitroxide multi-spin systems ' Journal of Organic Chemistry , vol 79 , no. 17 , pp. 8313–8323 . DOI: 10.1021/jo5015678
Journal of Organic Chemistry
Copyright © 2014 American Chemical Society. This is an open access article available under the terms of a Creative Commons Attribution 4.0 International licence (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html)
S.V. is supported by an EPSRC Doctoral Training Grant; B.E.B. acknowledges an EaStCHEM Hirst Academic Fellowship by the School of Chemistry, St Andrews and funding from the People Programme (Marie Curie Actions) of the European Union’s Seventh Framework Programme (REA 334496)
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