Halogen bonding between an Isoindoline Nitroxide and 1,4-Diiodotetrafluorobenzene: New tools and tectons for self-assembling organic spin systems

Hanson, Graeme R., Jensen, Paul, McMurtrie, John, Rintoul, Llew and Micallef, Aaron S. (2009) Halogen bonding between an Isoindoline Nitroxide and 1,4-Diiodotetrafluorobenzene: New tools and tectons for self-assembling organic spin systems. Chemistry: A European Journal, 15 16: 4156-4164. doi:10.1002/chem.200801920


Author Hanson, Graeme R.
Jensen, Paul
McMurtrie, John
Rintoul, Llew
Micallef, Aaron S.
Title Halogen bonding between an Isoindoline Nitroxide and 1,4-Diiodotetrafluorobenzene: New tools and tectons for self-assembling organic spin systems
Journal name Chemistry: A European Journal   Check publisher's open access policy
ISSN 0947-6539
1521-3765
Publication date 2009-04-14
Sub-type Article (original research)
DOI 10.1002/chem.200801920
Open Access Status
Volume 15
Issue 16
Start page 4156
End page 4164
Total pages 9
Editor Jan-Erling Bäckvall
Place of publication Berlin, Germany
Publisher Wiley-VCH
Language eng
Subject 0399 Other Chemical Sciences
030606 Structural Chemistry and Spectroscopy
030501 Free Radical Chemistry
970103 Expanding Knowledge in the Chemical Sciences
C1
Abstract Radical assembly: Halogen bonding has been observed for the first time between an isoindoline nitroxide and an iodoperfluorocarbon (see figure), which cocrystallize to form a discrete 2:1 supramolecular compound in which NO.I halogen bonding is the dominant intermolecular interaction. This illustrates the potential use of halogen bonding and isoindoline nitroxide tectons for the assembly of organic spin systems. 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 NO.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.
Keyword halogen bonding
nitroxides
noncovalent interactions
organic spin systems
radicals
Q-Index Code C1
Q-Index Status Confirmed Code

 
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Created: Thu, 03 Sep 2009, 18:14:33 EST by Mr Andrew Martlew on behalf of Centre For Magnetic Resonance