TY - JOUR
T1 - Synthesis of dendritic, non-kekulé-, and nondisjoint-type triphenylmethanes terminated with galvinoxyl radicals
AU - Fukuzaki, Eiji
AU - Takahashi, Naoki
AU - Imai, Shingo
AU - Nishide, Hiroyuki
AU - Rajca, Andrzej
PY - 2005
Y1 - 2005
N2 - A series of triphenylmethanes terminated with (a) hydrogalvinoxyl(s), bis(4-tert-butylphenyl)-(4-hydrogalvinoxylphenyl)methoxymethane lad, tris(4-hydrogalvinoxylphenyl)methoxymethane 2ad, and tris{4-[bis(4- hydrogalvinoxylphenyl)methoxymethyl]phenyl}methoxymethane 3ad, were prepared and oxidized to the corresponding galvinoxyl radicals, 1af, 2af, and 3af, which have one, three, and six galvinoxyl radical(s), respectively. Chemical reduction of the galvinoxyl radicals with a Na/K alloy gave stable intermediates, i.e., the tetraanion, decaanion, and docosaanion. The tetraanion was oxidized with an equimolar amount of iodine at ca. 170 K to the galvinoxyl radical-combined triphenylmethyl radical 1cf. The ESR signal of the biradical at room temperature indicated an exchange interaction between the two radicals. The spectrum at 140 K had a zero-field splitting and ΔMs= ±2 transition signal at half-field, which are characteristic of a multiplet species.
AB - A series of triphenylmethanes terminated with (a) hydrogalvinoxyl(s), bis(4-tert-butylphenyl)-(4-hydrogalvinoxylphenyl)methoxymethane lad, tris(4-hydrogalvinoxylphenyl)methoxymethane 2ad, and tris{4-[bis(4- hydrogalvinoxylphenyl)methoxymethyl]phenyl}methoxymethane 3ad, were prepared and oxidized to the corresponding galvinoxyl radicals, 1af, 2af, and 3af, which have one, three, and six galvinoxyl radical(s), respectively. Chemical reduction of the galvinoxyl radicals with a Na/K alloy gave stable intermediates, i.e., the tetraanion, decaanion, and docosaanion. The tetraanion was oxidized with an equimolar amount of iodine at ca. 170 K to the galvinoxyl radical-combined triphenylmethyl radical 1cf. The ESR signal of the biradical at room temperature indicated an exchange interaction between the two radicals. The spectrum at 140 K had a zero-field splitting and ΔMs= ±2 transition signal at half-field, which are characteristic of a multiplet species.
KW - Dendrimer
KW - Galvinoxyl Radical
KW - High-spin Molecule
KW - Non-Kekulé Structure
KW - Triphenylmethane
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U2 - 10.1295/polymj.37.284
DO - 10.1295/polymj.37.284
M3 - Article
AN - SCOPUS:19944401552
VL - 37
SP - 284
EP - 293
JO - Polymer Journal
JF - Polymer Journal
SN - 0032-3896
IS - 4
ER -