AN IMIDE ANION RADICAL THAT DIMERIZES AND ASSEMBLES INTO PI-STACKS IN SOLUTION

被引:115
作者
PENNEAU, JF
STALLMAN, BJ
KASAI, PH
MILLER, LL
机构
[1] IBM CORP,ALMADEN LABS,650 HARRY RD,SAN JOSE,CA 95120
[2] UNIV MINNESOTA,DEPT CHEM,MINNEAPOLIS,MN 55455
关键词
D O I
10.1021/cm00017a013
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
N,N'-Bis(4-phenysulfonate)-1,4,5,8-naphthalenetetracarboxylic diimide was prepared as the disodium and bis(tetrabutylammonium) salts. It was reduced electrochemically in DMF or water and by dithionite in water to a form an anion radical. On the basis of visible, NIR, IR, and ESR data, the anion radical is shown to be monomeric in DMF, dimeric in water, and aggregated in aqueous NaCl. The aggregates contain pi-stacks that are spectroscopically similar to the stacks found in a solid film of the anion radical.
引用
收藏
页码:791 / 796
页数:6
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共 33 条
[11]   AN ELECTRON-SPIN RESONANCE, ENDOR, AND TRIPLE RESONANCE STUDY OF METHYL-SUBSTITUTED N,N'-DIPHENYL-4,4'-BIPYRIDYLIUM DICHLORIDE RADICAL CATIONS [J].
EVANS, JC ;
EVANS, AG ;
NOURISORKHABI, NH ;
OBAID, AY ;
ROWLANDS, CC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (02) :315-318
[12]  
Ferraro J. R., 1987, INTRO SYNTHETIC ELEC
[13]   AN ALL-ORGANIC SOFT THIN-FILM TRANSISTOR WITH VERY HIGH CARRIER MOBILITY [J].
GARNIER, F ;
HOROWITZ, G ;
PENG, XH ;
FICHOU, D .
ADVANCED MATERIALS, 1990, 2 (12) :592-594
[14]   RADICAL-ANION SALTS OF NAPHTHALENETETRACARBOXYLIC ACID-DERIVATIVES - A NOVEL CLASS OF ELECTRICALLY CONDUCTING COMPOUNDS [J].
HEYWANG, G ;
BORN, L ;
FITZKY, HG ;
HASSEL, T ;
HOCKER, J ;
MULLER, HK ;
PITTEL, B ;
ROTH, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04) :483-485
[15]   ELECTRONIC INTERACTION IN KETYL RADICALS [J].
HIROTA, N ;
WEISSMAN, SI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (13) :2538-&
[16]   INFRARED-SPECTRA AND DIMER STRUCTURE OF REDUCED VIOLOGEN COMPOUNDS [J].
ITO, M ;
SASAKI, H ;
TAKAHASHI, M .
JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (15) :3932-3934
[17]   ORGANIC CONDUCTORS - EVIDENCE FOR CORRELATION-EFFECTS IN INFRARED PROPERTIES [J].
JACOBSEN, CS ;
JOHANNSEN, I ;
BECHGAARD, K .
PHYSICAL REVIEW LETTERS, 1984, 53 (02) :194-197
[18]   ELECTRONIC ABSORPTION SPECTRA OF DIMERS OF P-BENZOSEMIQUINONE ANION AND WURSTERS CATIONS IN SOLUTION [J].
KIMURA, K ;
YAMADA, H ;
TSUBOMURA, H .
JOURNAL OF CHEMICAL PHYSICS, 1968, 48 (01) :440-+
[19]   ESR AND ELECTROCHEMICAL STUDIES OF SELF ASSEMBLED OLIGOIMIDE MONOLAYERS ON GOLD [J].
KWAN, WSV ;
PENNEAU, JF ;
MILLER, LL .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1990, 291 (1-2) :295-299
[20]   PHENYL-CAPPED OCTAANILINE (COA) - AN EXCELLENT MODEL FOR POLYANILINE [J].
LU, FL ;
WUDL, F ;
NOWAK, M ;
HEEGER, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8311-8313