Hexathiophenalenyliums Cations: Syntheses, Structures, and Redox Chemistry

被引:11
作者
Bag, Pradip
Tham, Fook S.
Donnadieu, Bruno
Haddon, Robert C. [1 ]
机构
[1] Univ Calif Riverside, Dept Chem, Riverside, CA 92521 USA
关键词
RESONATING VALENCE-BOND; RADICAL PI-DIMERS; MOLECULAR CONDUCTORS; ORGANIC METALS; PHENALENYL RADICALS; GROUND-STATE; SIGMA-BOND; CRYSTAL; SUPERCONDUCTORS; DIMERIZATIONS;
D O I
10.1021/ol400452f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preparations of two hexathiophenalenylium compounds as stable salts from the reaction of 3,4,6,7-tetrathio-9-hydroxyphenalenone with Lawesson's reagent have been reported. The presence of three disulfide linkages on the periphery of the core phenalenyl unit is confirmed by X-ray crystallographic characterizations. Electrochemical cell potentials are lower than those of related dithio- and tetrathio-bridged phenalenyl radicals, and the hexathiophenalenyl radical shows a strong electron paramagnetic resonance (EPR) signal in the solid state.
引用
收藏
页码:1198 / 1201
页数:4
相关论文
共 53 条
[1]   ONE-DIMENSIONAL STACKING OF BIFUNCTIONAL DITHIAADIAZOLYL AND DISELENADIAZOLYL RADICALS - PREPARATION AND STRUCTURAL AND ELECTRONIC-PROPERTIES OF 1,3-[(E2N2C)C6H4(CN2E2)] (E = S, SE) [J].
ANDREWS, MP ;
CORDES, AW ;
DOUGLASS, DC ;
FLEMING, RM ;
GLARUM, SH ;
HADDON, RC ;
MARSH, P ;
OAKLEY, RT ;
PALSTRA, TTM ;
SCHNEEMEYER, LF ;
TRUCKS, GW ;
TYCKO, R ;
WASZCZAK, JV ;
YOUNG, KM ;
ZIMMERMAN, NM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) :3559-3568
[2]   Resonating Valence Bond and σ-Charge Density Wave Phases in a Benzannulated Phenalenyl Radical [J].
Bag, Pradip ;
Itkis, Mikhail E. ;
Pal, Sushanta K. ;
Donnadieu, Bruno ;
Tham, Fook S. ;
Park, Hyunsoo ;
Schlueter, John A. ;
Siegrist, Theo ;
Haddon, Robert C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) :2684-2694
[3]   Spontaneous magnetization in a sulfur-nitrogen radical at 36 K [J].
Banister, AJ ;
Bricklebank, N ;
Lavender, I ;
Rawson, JM ;
Gregory, CI ;
Tanner, BK ;
Clegg, W ;
Elsegood, MRJ ;
Palacio, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (21) :2533-2535
[4]   Introduction: Molecular conductors [J].
Batail, P .
CHEMICAL REVIEWS, 2004, 104 (11) :4887-4890
[5]   Pressure enhanced conductivity in bis-1,2,3-thiaselenazolyl dimers [J].
Beer, L ;
Brusso, JL ;
Haddon, RC ;
Itkis, ME ;
Kleinke, H ;
Leitch, AA ;
Oakley, RT ;
Reed, RW ;
Richardson, JF ;
Secco, RA ;
Yu, XY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18159-18170
[6]   Tetrathiophenalenyl radical and its disulfide-bridged dimer [J].
Beer, Leanne ;
Reed, Robert W. ;
Robertson, Craig M. ;
Oakley, Richard T. ;
Tham, Fook S. ;
Haddon, Robert C. .
ORGANIC LETTERS, 2008, 10 (14) :3121-3123
[7]   The first electronically stabilized phenalenyl radical: Effect of substituents on solution chemistry and solid-state structure [J].
Beer, Leanne ;
Mandal, Swadhin K. ;
Reed, Robert W. ;
Oakley, Richard T. ;
Tham, Fook S. ;
Donnadieu, Bruno ;
Haddon, Robert C. .
CRYSTAL GROWTH & DESIGN, 2007, 7 (04) :802-809
[8]   Bistabilities in 1,3,2-dithiazolyl radicals [J].
Brusso, JL ;
Clements, OP ;
Haddon, RC ;
Itkis, ME ;
Leitch, AA ;
Oakley, RT ;
Reed, RW ;
Richardson, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8256-8265
[9]   A molecule like sodium [J].
Cordes, AW ;
Haddon, RC ;
Oakley, RT .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (4-5) :673-684
[10]   Room-temperature magnetic bistability in organic radical crystals [J].
Fujita, W ;
Awaga, K .
SCIENCE, 1999, 286 (5438) :261-262