Multi-stage amphoteric redox hydrocarbons based on a phenalenyl radical

被引：51

作者：

Nakasuji, K ^{[1
]}

Kubo, T ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2004年 / 77卷 / 10期

关键词：

D O I：

10.1246/bcsj.77.1791

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Molecular design and properties of amphoteric redox hydrocarbons are reviewed. Our molecular design is based on a phenalenyl radical, which has a non-bonding molecular orbital with an occupation number of one and is known to behave as a two-stage amphoteric redox system. We have prepared eight amphoteric redox compounds containing two or three phenalenyl units. Cyclic voltammetry showing small E-1(sum) values confirms the high amphotericity of these compounds. The properties of ionic redox species generated are also investigated. At the last part of this account, we show some aspects of a singlet biradicaloid character that originates from a small HOMO-LUMO gap.

引用

页码：1791 / 1801

页数：11

共 54 条

[1] DIMETHYL-SULFOXIDE PHASE C-H BOND-DISSOCIATION ENERGIES FOR PHENALENE AND BENZANTHRENE [J].

BAUSCH, MJ ;

GOSTOWSKI, R ;

JIRKA, G ;

SELMARTEN, D ;

WINTER, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5805-5806

[2] ESR AND ENDOR STUDIES OF PARTIALLY DEUTERATED AND CHLORINATED PHENALENYLS - NEW SYNTHETIC PATHWAYS [J].

BIEHL, R ;

HASS, C ;

KURRECK, H ;

LUBITZ, W ;

OESTREICH, S .

TETRAHEDRON, 1978, 34 (04) :419-424

[3] GENERAL TRIPLE RESONANCE ON FREE-RADICALS IN SOLUTION - DETERMINATION OF RELATIVE SIGNS OF ISOTROPIC HYPERFINE COUPLING-CONSTANTS [J].

BIEHL, R ;

PLATO, M ;

MOBIUS, K .

JOURNAL OF CHEMICAL PHYSICS, 1975, 63 (08) :3515-3522

[4] AN INVESTIGATION OF THE PREPARATION AND SOME PROPERTIES OF PERINAPHTHENE [J].

BOEKELHEIDE, V ;

LARRABEE, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (03) :1245-1249

[5] HYDRIDE IONS IN ORGANIC REACTIONS .1. DEHYDROGENATION BY TRIPHENYLMETHYL PERCHLORATE [J].

BONTHRONE, W ;

REID, DH .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (SEP-O) :2773-2779

[6] ESR, H-1-ENDOR, D-ENDOR, C-13-ENDOR AND TRIPLE RESONANCE STUDIES OF ALKYL SUBSTITUTED PHENALENYL RADICALS [J].

BROSER, W ;

KURRECK, H ;

OESTREICHJANZEN, S ;

SCHLOMP, G ;

FEY, HJ ;

KIRSTE, B .

TETRAHEDRON, 1979, 35 (09) :1159-1166

[7] Dimeric phenalenyl-based neutral radical molecular conductors [J].

Chi, X ;

Itkis, ME ;

Kirschbaum, K ;

Pinkerton, AA ;

Oakley, RT ;

Cordes, AW ;

Haddon, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (17) :4041-4048

[8] The first phenalenyl-based neutral radical molecular conductor [J].

Chi, X ;

Itkis, ME ;

Patrick, BO ;

Barclay, TM ;

Reed, RW ;

Oakley, RT ;

Cordes, AW ;

Haddon, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) :10395-10402

[9] Electronic structure of a stable phenalenyl radical as studied by ESR/ENDOR, paramagnetic NMR spectroscopy and SQUID measurements [J].

Fukui, K ;

Sato, K ;

Shiomi, D ;

Takui, T ;

Itoh, K ;

Kubo, T ;

Gotoh, K ;

Yamamoto, K ;

Nakasuji, K ;

Naito, A .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1999, 334 :49-58

[10] Electronic structure of a stable phenalenyl radical in crystalline state as studied by SQUID measurements, cw-ESR, and 13C CP MAS NMR spectroscopy [J].