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Nitroxide spin probes for magnetic resonance characterization of ordered systems

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2001

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Dragutan, Ileana
Dragutan, Valerian
Caragheorgheopol, Agneta
Zarkadisc, Antonios K.
Hoffmann, Heinz

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Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2001, 183-185, pp. 767-776. ISSN 0927-7757. eISSN 1873-4359. Available under: doi: 10.1016/S0927-7757(01)00503-9

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Stable free radicals belonging to different classes have been synthesized in view of potential applications in studies of organized systems. Among them a new pyrroline nitroxide with a high fluorine content, 2,2,5,5-tetramethyl-3-pyrrolin-1-yloxy-3-[(1H,1H-perfluoro-1-octoxy)carbonyl] (3), apt to probe the hydrophobic perfluoro-rich domains inside macroaggregates, has been prepared by a rarely encountered approach namely the spin-labelling of the very cosurfactant participating in the self-assembling process. Emphasis has then been laid upon the synthesis of further stable free radicals from the group of substituted nitronyl nitroxides. A general experimental procedure has been adapted according to the nature of the 2-substituent, resulting in a series of nitronyl nitroxides with a wide range of hydrophobicity and showing spectral parameters in good agreement with literature values. Using the spin probe-electron spin resonance technique, 3 and the 1-H-imidazol-1-yloxy-4,5-dihydro-4,4,5,5-tetramethyl-2-ethyl-3-oxide (7, R=C2H5) or the 1-H-imidazol-1-yloxy-4,5-dihydro-4,4,5,5-tetramethyl-2-undecyl-3-oxide (7, R=C11H23) have been applied in ESR investigations on vesicle phases of a zwitterionic surfactant (TDMAO)/perfluorocosurfactant (PFC) system and on Triton X-100 reverse micelles, respectively. While spin probe 3 proved to be insensitive to differences between the charged and uncharged phases, probes 7 were able to detect changes in the micelle micropolarity induced by hydration. The results corroborate well with previous UV measurements in the Triton X-100 system using the same probes 7.

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ISO 690DRAGUTAN, Ileana, Valerian DRAGUTAN, Agneta CARAGHEORGHEOPOL, Antonios K. ZARKADISC, Helmut FISCHER, Heinz HOFFMANN, 2001. Nitroxide spin probes for magnetic resonance characterization of ordered systems. In: Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2001, 183-185, pp. 767-776. ISSN 0927-7757. eISSN 1873-4359. Available under: doi: 10.1016/S0927-7757(01)00503-9
BibTex
@article{Dragutan2001Nitro-22962,
  year={2001},
  doi={10.1016/S0927-7757(01)00503-9},
  title={Nitroxide spin probes for magnetic resonance characterization of ordered systems},
  volume={183-185},
  issn={0927-7757},
  journal={Colloids and Surfaces A: Physicochemical and Engineering Aspects},
  pages={767--776},
  author={Dragutan, Ileana and Dragutan, Valerian and Caragheorgheopol, Agneta and Zarkadisc, Antonios K. and Fischer, Helmut and Hoffmann, Heinz}
}
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    <dcterms:abstract xml:lang="eng">Stable free radicals belonging to different classes have been synthesized in view of potential applications in studies of organized systems. Among them a new pyrroline nitroxide with a high fluorine content, 2,2,5,5-tetramethyl-3-pyrrolin-1-yloxy-3-[(1H,1H-perfluoro-1-octoxy)carbonyl] (3), apt to probe the hydrophobic perfluoro-rich domains inside macroaggregates, has been prepared by a rarely encountered approach namely the spin-labelling of the very cosurfactant participating in the self-assembling process. Emphasis has then been laid upon the synthesis of further stable free radicals from the group of substituted nitronyl nitroxides. A general experimental procedure has been adapted according to the nature of the 2-substituent, resulting in a series of nitronyl nitroxides with a wide range of hydrophobicity and showing spectral parameters in good agreement with literature values. Using the spin probe-electron spin resonance technique, 3 and the 1-H-imidazol-1-yloxy-4,5-dihydro-4,4,5,5-tetramethyl-2-ethyl-3-oxide (7, R=C2H5) or the 1-H-imidazol-1-yloxy-4,5-dihydro-4,4,5,5-tetramethyl-2-undecyl-3-oxide (7, R=C11H23) have been applied in ESR investigations on vesicle phases of a zwitterionic surfactant (TDMAO)/perfluorocosurfactant (PFC) system and on Triton X-100 reverse micelles, respectively. While spin probe 3 proved to be insensitive to differences between the charged and uncharged phases, probes 7 were able to detect changes in the micelle micropolarity induced by hydration. The results corroborate well with previous UV measurements in the Triton X-100 system using the same probes 7.</dcterms:abstract>
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