Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 21, Pages 8025-8036Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo034723n
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A series of bis-iminonitroxide diradical derivatives of different lengths and geometry have been prepared that incorporate a conjugated phenylene-ethynylene bridge as a rigid spacer. This paper describes the synthesis of these new components and their main characterizations. An unexpected singlet ground state and substituent effects on the singlet-triplet gap have been found for substituted m-phenylene-based diradicals. The effects of the pi-conjugation on the intramolecular through-bond spin coupling have been investigated by changing the length of the spacer within linear derivatives. The EPR studies demonstrate the intramolecular magnetic coupling between the radical spins within all compounds. This result is very attractive and unusual, given the large distance between the radicals from 15 Angstrom in the dimer to 36 Angstrom in the pentamer.
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