期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 16, 页码 4156-4164出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801920
关键词
halogen bonding; nitroxides; noncovalent interactions; organic spin systems; radicals
资金
- Australian Research Council
The isoindoline nitroxide 1,1,3,3-tetramethylisoindolin-2-yloxyl (TMIO) and 1,4-diiodotetrafluorobenzene readily form a discrete 2:1 complex that shows evidence of relatively strong N-O-center dot center dot center dot center dot I halogen bonding. This interaction was characterized in the solid state by single-crystal X-ray analysis, thermal analysis, and vibrational spectroscopy (IR and Raman), backed by density functional theory calculations. EPR spectroscopy performed on a solution of TMIO in pentafluoroiodobenzene, a halogen-bonding donor, indicates that halogen bonding induces an increase in electron density at the nitroxide nitrogen nucleus and an increase in the nitroxide rotational correlation time. Our findings demonstrate the potential of utilizing halogen-bonding interactions to promote the self-assembly of new isoindoline nitroxide tectons for the preparation of organic spin systems.
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