The effects of conjugation path variation on electron delocalization in phenoxyl-based systems

Molecules

Volumn 9, Issue 9, 2004, Pages 725-745

  Liu, Yanbing ^a   Lahti, Paul M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

2,6 Di tert butylphenoxyl; Conjugated polyradicals; Electron spin resonance; Exchange; Hyperfine coupling; Molecular magnetism; Spin delocalization

Indexed keywords

BENZENE DERIVATIVE; CARBONYL DERIVATIVE; RADICAL; VINYL DERIVATIVE;

ARTICLE; ELECTRON; ELECTRON SPIN RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 5444261803     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/90900725     Document Type: Article

References (38)

1. (a) Mataga, N. "Possible 'Ferromagnetic States" of Some Hypothetical Hydrocarbons" Theor. Chim. Acta 1968, 10, 372-376;
2. (b) Ovchinnikov, A. A. "Multiplicity of Ground-State of Large Alternant Organic Molecules with Conjugated Bonds" Theor. Chim. Acta 1978, 47, 297-304;
3. (c) Borden, W. T.; Davidson, E. R. "Electron Repulsion in Diradicals" J. Am. Chem. Soc. 1977, 99, 4587;
4. (d) Borden, W. T., Ed.; Diradicals; John Wiley and Sons, Inc.: New York, 1982.
5. Rajca, A. "Organic Diradicals and Polyradicals: From Spin Coupling to Magnetism?" Chem. Rev. 1994, 94, 871.
6. (a) Rajca, A.; Wongsriratanakul, J.; Rajca, S. "Magnetic ordering in an organic polymer" Science 2001, 294, 1503-1505;
7. (b) Rajca, A. "From high-spin organic molecules to organic polymers with magnetic ordering" Chem. Eur. J. 2002, 8, 4834-4841.
8. (a) Koga, N.; Inoue, K.; Sasagawa, N.; Iwamura, H. "Magnetic properties of microcrystalline "poly(phenyldiacetylenes)" carrying radical or carbene centers on the side chains" Mater. Res. Soc. Symp. Proc. 1990, 173, 39-49;
9. (b) Abdelkader, M.; Drenth, W.; Meijer, E. W. "Synthesis and Characterization of a Stable Poly(iminomethylene) with Pendant Phenoxyl Radicals" Chem. Mater. 1991, 3, 598;
10. (c) Fujii, A.; Ishida, T.; Koga, N.; Iwamura, H. "Syntheses and magnetic properties of poly(phenylacetylenes) carrying a (1-oxido-3-oxy-4,4,5,5- tetramethyl-2-imidazolin-2-yl) group at the meta or para position of the phenyl ring" Macromolecules 1991, 24, 1077-1082;
11. (d) Miura, Y.; Inui, K.; Yamaguchi, F.; Inoue, M.; Teki, Y.; Takui, T.; Itoh, K. "Molecular design, synthesis, and magnetic characterization of poly(phenylacetylene) with pi-toporegulated pendant nitronyl nitroxide radicals as models for organic superpara- and ferromagnets" J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 959-966;
12. (e) Nishide, H. "High-spin alignment in .pi.-conjugated polyradicals. A magnetic polymer" Adv. Mater. 1995, 7, 937-941;
13. (f) Nishide, H.; Ozawa, T.; Miyasaka, M.; Tsuchida, E. "A nanometer-sized high-spin polyradical: Poly(4-phenoxyl-1,2-phenylenevinylene) planarily extended in a non-Kekulé fashion and its magnetic force microscopic images" J. Am. Chem. Soc. 2001, 123, 5942-5946;
14. (g) Miyasaka, M.; Saito, Y.; Nishide, H. "Magnetic force microscopy images of a nanometer-sized purely organic high-spin polyradical" Adv. Funct. Mater. 2003, 13, 113-117.
15. Lahti, P. M.; Ichimura, A. S. "A Semiempirical Study of Electron Exchange Interaction in Organic High-Spin Pi-Systems - Classifying Structural Effects in Organic Magnetic Molecules" J. Org. Chem. 1991, 56, 3030-3042.
16. Lahti, P. M. "The Design of Organic Based Materials with Controlled Magnetic Properties", In Molecule-Based Magnetic Materials. Theory, Techniques, and Applications; Turnbull, M. M.; Sugimoto, T.; Thompson, L. K., Eds.; American Chemical Society: Washington, DC, 1996; Vol. 644, pp. 218-235.
17. Nishide, H.; Miyasaka, M.; Tsuchida, E. "Average Octet Radical Polymer: A Stable Polyphenoxyl with Star-Shaped pi- Conjugation" Angew. Chem. Int. Ed. 1998, 37, 2400-2402.
18. (a) Modarelli, D. A.; Rossitto, F. C.; Lahti, P. M. "Convenient Unimolecular Sources of Aryloxyl Radicals. I. Aryloxyoxalyl Chlorides" Tetrahedron Lett. 1989, 30, 4473-4476;
19. (b) Modarelli, D. A.; Rossitto, F. C.; Lahti, P. M. "Convenient Unimolecular Sources of Aryloxyl Radicals .2. Aryloxyoxalyl Tert- Butylperoxides" Tetrahedron Lett. 1989, 30, 4477-4480;
20. (c) Modarelli, D. A.; Lahti, P. M. "Diaryl Oxalates as Convenient Unimolecular Sources of Aryloxyl Radicals" Chem. Commun. 1990, 1167-1168;
21. (d) Rossitto, F. C.; Lahti, P. M. "Poly[3,5-Di-Tert-Butyl-4-[(2,4,6- Tri-Tert-Butylphenyl)Oxalato]Phenylacetylene] - a Photochemical Precursor to a Conjugated Polyradical" Macromolecules 1993, 26, 6308-6309;
22. (e) Lahti, P. M.; Modarelli, D. A.; Rossitto, F. C.; Inceli, A. L.; Ichimura, A. S.; Ivatury, S. "Aryl Oxalate Derivatives as Convenient Precursors for Generation of Aryloxyl Radicals" J. Org. Chem. 1996, 61, 1730-1738;
23. (f) Lahti, P. M.; Inceli, A. L.; Rossitto, F. C. "Synthesis, Characterization, and Photolysis of Poly[3,5-tert-butyl-4-[(2,4,6-tri-tert- butylphenyl)oxalato]phenylacetylene], a Photochemical Polyradical Precursor" J. Polym. Sci. Part A, Polym. Chem. 1997, 35, 2167-2176.
24. (a) Wolf, S. A.; Awschalom, D. D.; Buhrman, R. A.; Daughton, J. M.; von Molnar, S.; Roukes, M. L.; Chtchelkanova, A. Y.; Treger, D. M. "Spintronics: A Spin-Based Electronics Vision for the Future", Science 2001, 1488-1495;
25. (b) Xiong, Z. H.; Wu, D.; Vardeny, Z. V.; Shi, J. "Giant magnetoresistance in organic spin-valves" Nature 2004, 427, 821 - 824.
26. Becker, H.-D. "New Stable Phenoxy Radicals. The Oxidation of Hydroxystilbenes." J. Org. Chem. 1969, 34, 1211-1215.
27. Duling, D. R. "Simulation of Multiple Isotropic Spin Trap EPR Spectra" J. Magn. Res. 1994, B104, 105-110.
28. Weil, J. A.; Bolton, J. R.; Wertz, J. E. "Electron Paramagnetic Resonance: Elementary Theory and Practical Applications"; Wiley: New York, NY, 1986; pp. 182-186.
29. 1H-NMR and ESR Investigations of Aryl-t-Butyl Nitroxides and Nitronylnitroxides" Tetrahedron 1973, 29, 3833-3842.
30. Lahti, P. M.; Esat, B.; Ferrer, J. R.; Liu, Y.; Marby, K. A.; Xie, C.; George, C.; Antorrena, G.; Palacio, F. "Polymeric, H-bonded, and chelatable phenoxyl and nitroxide radicals" Mol. Cryst. Liq. Cryst. 1999, 334, 285-294.
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 98; Gaussian Inc.: Pittsburgh, PA, 1998.
32. Brigati, G.; Lucarini, M.; Mugnaini, V.; Pedulli, G. F. "Determination of the Substituent Effect on the O-H Bond Dissociation Enthalpies of Phenolic Antioxidants by the EPR Radical Equilibration Technique" J. Org. Chem. 2002, 67, 4828-4832.
33. Sundberg, R. J.; Heintzelman, R. W. "Reactivity of aryl nitrenes. Competition between carbazole formation and internal bond reorganization in biphenylnitrenes" J. Org. Chem. 1974, 39, 2546-2552.
34. Zeng, F.; Zimmerman, S. C. "Rapid Synthesis of Dendrimers by an Orthogonal Coupling Strategy" J. Amer. Chem. Soc. 1996, 118, 5326-5327.
35. Harrer, W.; Kurreck, H.; Reusch, J.; Gierko, W. "Über galvinole und galvinoxylmehrspinsysteme - I : Eine neue metallorganische synthese von mono- und oligo-galvinolen" Tetrahedron 1975, 31, 625-632.
36. Satoh, Y.; Shi, C. "An Efficient Synthesis of 4-Aryl-2,6-di-tert- butylphenols by a Palladiuim Catalyzed Cross-Coupling Reaction" Synthesis 1994, 1146-1148
37. Nekhoroshev, M. V.; Ivakhnenko, E. P.; Okhlobystin, O. Yu "Methods for the acylation of sterically hindered phenols" Zh. Obshch. Khim. 1977, 13, 662.
38. Braun, D.; Wittig, W. "Stable polyphenoxyls. 4. Polymers from sterically hindered, protected vinylphenols" Makromol. Chem. 1980, 181, 557-563.