Three-Dimensional Intramolecular Exchange Interaction in a Curved and Nonalternant π-Conjugated System: Corannulene with Two Phenoxyl Radicals

被引：72

作者：

Ueda, Akira ^{[1
]}

Nishida, Shinsuke ^{[2
,3
]}

Fukui, Kozo ^{[4
]}

Ise, Tomoaki ^{[2
,3
]}

Shiomi, Daisuke ^{[2
,3
]}

Sato, Kazunobu ^{[2
,3
]}

Takui, Takeji ^{[2
,3
]}

Nakasuji, Kazuhiro ^{[1
]}

Morita, Yasushi ^{[1
,4
]}

机构：

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

[2] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, Osaka 5588585, Japan

[3] Osaka City Univ, Grad Sch Sci, Dept Mat Sci, Sumiyoshi Ku, Osaka 5588585, Japan

[4] Japan Sci & Technol Agcy, PRESTO, Tokyo, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 09期

基金：

日本学术振兴会;

关键词：

conjugation; density functional calculations; EPR spectroscopy; exchange interactions; radicals; INVERSION BARRIER; AROMATICITY; C-60(2-); DELOCALIZATION; DERIVATIVES; MOLECULES; FULLERENE; SURFACE; ANIONS;

D O I：

10.1002/anie.200906666

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

"Chemical Equation Presented" A neutral diradical based on corannulene with curved and nonalternant π conjugation has been synthesized and isolated as air-stable crystals. Sizable spin derealization and strong intramolecular exchange interaction in the intrinsically three-dimensional π network (see picture), as well as significant diradical contributions in the ground state, were experimentally disclosed. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1678 / 1682

页数：5

共 46 条

[1] Antiaromaticity in open-shell cyclopropenyl to cycloheptatrienyl cations, anions, free radicals, and radical ions [J].

Allen, AD ;

Tidwell, TT .

CHEMICAL REVIEWS, 2001, 101 (05) :1333-1348

[2] DIBENZO[GHI,MNO]FLUORANTHENE [J].

BARTH, WE ;

LAWTON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (02) :380-&

[3] SYNTHESIS AND ELECTRONIC CHARACTERIZATION OF DISCRETE BUCKMINSTERFULLERIDE SALTS - C-60(2-) AND C-60(3-) [J].

BHYRAPPA, P ;

PAUL, P ;

STINCHCOMBE, J ;

BOYD, PDW ;

REED, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11004-11005

[4]

Borden W.T., 1982, DIRADICALS

[5] THE C-60(2-) FULLERIDE ION [J].

BOYD, PDW ;

BHYRAPPA, P ;

PAUL, P ;

STINCHCOMBE, J ;

BOLSKAR, RD ;

SUN, YP ;

REED, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) :2907-2914

[6] Electrochemical and Theoretical Investigation of Corannulene Reduction Processes [J].

Bruno, Carlo ;

Benassi, Rois ;

Passalacqua, Alessio ;

Paolucci, Francesco ;

Fontanesi, Claudio ;

Marcaccio, Massimo ;

Jackson, Edward A. ;

Scott, Lawrence T. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (07) :1954-1962

[7]

DOHNERT D, 1980, J AM CHEM SOC, V102, P1789

[8]

Dresselhaus M. S., 2001, CARBON NANOTUBES SYN

[9] Deflected spin transmission from radical substituent to corannulene's curved surface: Density functional theory calculations [J].

Fukui, K ;

Morita, Y ;

Nishida, S ;

Kobayashi, T ;

Sato, K ;

Shiomi, D ;

Takui, T ;

Nakasuji, K .

POLYHEDRON, 2005, 24 (16-17) :2326-2329

[10] PI-ORBITAL CONJUGATION AND REHYBRIDIZATION IN BRIDGED ANNULENES AND DEFORMED MOLECULES IN GENERAL - PI-ORBITAL AXIS VECTOR ANALYSIS [J].

HADDON, RC ;

SCOTT, LT .

PURE AND APPLIED CHEMISTRY, 1986, 58 (01) :137-142

← 1 2 3 4 5 →