Recent Advances in the Chemistry of Phenalenyl

被引:40
作者
Uchida, Kazuyuki [1 ]
Kubo, Takashi [1 ]
机构
[1] Osaka Univ, Grad Sch Sci, Dept Chem, Machikaneyama 1-1, Toyonaka, Osaka 5600043, Japan
关键词
SIGMA-BOND; STACKING INTERACTIONS; ELECTRONIC-STRUCTURE; CRYSTAL-STRUCTURES; PI-DIMER; RADICALS; DIMERIZATIONS; SPECTROSCOPY; STATE; HEXAFLUOROBENZENE;
D O I
10.5059/yukigoseikyokaishi.74.1069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenalenyl radical is an odd-alternant hydrocarbon radical with a highly symmetric (D-3h) structure. The high stability and amphoteric redox nature of this radical have triggered studies on its chemical reactivity, physical properties, and functionalities. The main problem hindering the use of phenalenyl radicals as the molecular components of functional materials is their propensity to sigma-dimerization. Challenging issue will lie in understanding the self-association character and also in controlling the molecular overlap motif. This article summarizes our studies on the self-association behavior of phenalenyl radicals.
引用
收藏
页码:1069 / 1077
页数:9
相关论文
共 43 条
[1]   SOLID-STATE INTERACTIONS IN RADICALS - CRYSTAL-STRUCTURES OF ALPHA-10-PHENYL-5(10H)-PHENAZINL AND BETA-10-PHENYL-5(10H)-PHENAZINYL [J].
BARTH, T ;
KANELLAKOPULOS, B ;
KRIEGER, C ;
NEUGEBAUER, FA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (21) :1626-1628
[2]   STEREOCHEMICALLY NONRIGID ORGANOMETALLIC COMPOUNDS .I. PI-CYCLOPENTADIENYLIRON DICARBONYL SIGMA-CYCLOPENTADIENE [J].
BENNETT, MJ ;
COTTON, FA ;
DAVISON, A ;
FALLER, JW ;
LIPPARD, SJ ;
MOREHOUS.SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (19) :4371-&
[3]   DEGENERATE AND PSEUDODEGENERATE 1,3-NITROGEN SHIFTS IN SULFUR NITROGEN CHEMISTRY - N-15 NMR ANALYSIS OF SKELETAL SCRAMBLING IN PHCN5S3 [J].
BESTARI, KT ;
BOERE, RT ;
OAKLEY, RT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1579-1584
[4]   LINEAR MAGNETIC CHAINS WITH ANISOTROPIC COUPLING [J].
BONNER, JC ;
FISHER, ME .
PHYSICAL REVIEW, 1964, 135 (3A) :A640-+
[5]   Phenyl-perfluorophenyl stacking interactions: A new strategy for supermolecule construction [J].
Coates, GW ;
Dunn, AR ;
Henling, LM ;
Dougherty, DA ;
Grubbs, RH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) :248-251
[6]   Control of single crystal structure and liquid crystal phase behaviour via arene-perfluoroarene interactions [J].
Dai, CY ;
Nguyen, P ;
Marder, TB ;
Scott, AJ ;
Clegg, W ;
Viney, C .
CHEMICAL COMMUNICATIONS, 1999, (24) :2493-2494
[7]   A magnetic resonance study of complex formation between the neutral phenalenyl radical and alkali metal ions in dilute alcohol solutions [J].
Dwyer, DW ;
Ciraolo, MF ;
Gilbert, DC ;
Doetschman, DC .
JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (32) :7629-7634
[8]   Electronic structure of a stable phenalenyl radical in crystalline state as studied by SQUID measurements, cw-ESR, and 13C CP MAS NMR spectroscopy [J].
Fukui, K ;
Sato, K ;
Shiomi, D ;
Takui, T ;
Itoh, K ;
Gotoh, K ;
Kubo, T ;
Yamamoto, K ;
Nakasuji, K ;
Naito, A .
SYNTHETIC METALS, 1999, 103 (1-3) :2257-2258
[9]   Supramolecular assemblies of hydrogen-bonded carboxylic acid dimers mediated by phenyl-pentafluorophenyl stacking interactions [J].
Gdaniec, M ;
Jankowski, W ;
Milewska, MJ ;
Poloñski, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3903-3906
[10]   NOTIZ UBER DAS ESR.-SPEKTRUM DES PHENALENYL-RADIKALS [J].
GERSON, F .
HELVETICA CHIMICA ACTA, 1966, 49 (05) :1463-+