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
相关论文
共 33 条
[1]   POLYARYLENES AND POLYARYLENEVINYLENES .2. OLIGORYLENE AS A MODEL FOR POLY(PERINAPHTHALENE) [J].
BOHNEN, A ;
KOCH, KH ;
LUTTKE, W ;
MULLEN, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05) :525-527
[2]   SOLUTION DIMERIZATION OF TETRACYANOQUINODIMETHANE ION RADICAL [J].
BOYD, RH ;
PHILLIPS, WD .
JOURNAL OF CHEMICAL PHYSICS, 1965, 43 (09) :2927-&
[3]   STUDIES ON IODINE DOPED THIOPHENE OLIGOMERS [J].
CAO, Y ;
GUO, D ;
PANG, M ;
QIAN, RY .
SYNTHETIC METALS, 1987, 18 (1-3) :189-194
[4]   MODIFICATION OF PHOTOCHEMICAL REACTIVITY BY ZEOLITES - PREPARATION AND SPECTROSCOPIC CHARACTERIZATION OF POLARONS AND BIPOLARONS OF THIOPHENE OLIGOMERS WITHIN THE CHANNELS OF PENTASIL ZEOLITES - THE EVOLUTION OF ORGANIC RADICAL IONS INTO CONDUCTING POLYMERS [J].
CASPAR, JV ;
RAMAMURTHY, V ;
CORBIN, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :600-610
[5]   SPECTROSCOPIC STUDIES OF BIPOLARONS FROM OLIGOMERIZED 3-METHOXYTHIOPHENE IN SOLUTION [J].
CHANG, AC ;
MILLER, LL .
SYNTHETIC METALS, 1987, 22 (01) :71-78
[6]  
DESORGO M, 1972, J PHYS CHEM-US, V76, P3468, DOI DOI 10.1021/J100667A029
[7]   SOLUBLE OLIGOIMIDE MOLECULAR LINES WHICH HAVE PERSISTENT POLY(ANION RADICALS) AND POLY(DIANIONS) [J].
DIETZ, TM ;
STALLMAN, BJ ;
KWAN, WSV ;
PENNEAU, JF ;
MILLER, LL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) :367-369
[8]  
DUFF DJ, 1975, COMPR TREAT, V4, pCH3
[9]   GEOMETRICAL STRUCTURE AND ABSORPTION SPECTRUM OF A CYANINE DYE AGGREGATE [J].
EMERSON, ES ;
CONLIN, MA ;
ROSENOFF, AE ;
NORLAND, KS ;
RODRIGUE.H ;
CHIN, D ;
BIRD, GR .
JOURNAL OF PHYSICAL CHEMISTRY, 1967, 71 (08) :2396-&
[10]   ELECTRON-SPIN RESONANCE STUDY OF DIMERIZATION EQUILIBRIUM OF RADICAL CATION OF 1,1'-DIETHYL-4,4'-BIPYRIDYLIUM DIIODIDE IN METHANOL [J].
EVANS, AG ;
EVANS, JC ;
BAKER, MW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (18) :5882-5884