New soluble bis[nona-, octa-, and pentamethylferrocenes] as ''molecular wires'' with a metal-to-metal distance of up to 40 angstrom

被引:106
作者
Hradsky, A
Bildstein, B
Schuler, N
Schottenberger, H
Jaitner, P
Ongania, KH
Wurst, K
Launay, JP
机构
[1] UNIV INNSBRUCK, INST ALLGEMEINE ANORGAN & THEORET CHEM, A-6020 INNSBRUCK, AUSTRIA
[2] UNIV INNSBRUCK, INST ORGAN CHEM, A-6020 INNSBRUCK, AUSTRIA
[3] CNRS, CTR ELABORAT MAT & ETUD STRUCT, GRP MOL ELECT, F-31055 TOULOUSE, FRANCE
关键词
D O I
10.1021/om960676w
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Methylated ferrocenes are useful building blocks for navel materials in molecular electronics with advantageous properties in comparison to normal ferrocene derivatives. The presence of nine, eight, or five methyl substituents leads to (i) a decrease in oxidation potential, (ii) amplified donor capacity with correspondingly increased stability of the ferrocenium salts, and, most significantly, (iii) increased solubility. A modular synthetic approach based on standard Wittig chemistry affords pi-conjugated soluble nona-, octa-, and pentamethylated biferrocenes, bridged by up to five vinylene-phenylene subunits. These biferrocenes with spacers are ''molecular wires'' with a metal-to-metal distance of up to 40 Angstrom and an effective conjugation pathway of up to 50 Angstrom.
引用
收藏
页码:392 / 402
页数:11
相关论文
共 68 条
  • [31] LAUNAY JP, UNPUB
  • [32] A NEW-TYPE OF BLUE-LIGHT-EMITTING ELECTROLUMINESCENT POLYMER
    LEE, JK
    SCHROCK, RR
    BAIGENT, DR
    FRIEND, RH
    [J]. MACROMOLECULES, 1995, 28 (06) : 1966 - 1971
  • [33] INTERVALENCE TRANSFER IN SUBSTITUTED BIFERROCENE CATIONS
    LEVANDA, C
    BECHGAARD, K
    COWAN, DO
    RAUSCH, MD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (09) : 2964 - 2968
  • [34] STABLE AND CRYSTALLINE ALLYLIUM AND ALLENYLIUM SALTS WITH FERROCENYL SUBSTITUENTS
    LUKASSER, J
    ANGLEITNER, H
    SCHOTTENBERGER, H
    KOPACKA, H
    SCHWEIGER, M
    BILDSTEIN, B
    ONGANIA, KH
    WURST, K
    [J]. ORGANOMETALLICS, 1995, 14 (12) : 5566 - 5578
  • [35] STRUCTURAL-PROPERTIES AND PHYSICAL-PROPERTIES OF DELOCALIZED MIXED-VALENT [CP-ASTERISK-M(PENTALENE)M'CP-ASTERISK](N+) AND [CP-ASTERISK-M(INDACENE)M'CP-ASTERISK](N+) (M, M'=FE, CO, NI, N=0, 1, 2) COMPLEXES
    MANRIQUEZ, JM
    WARD, MD
    REIFF, WM
    CALABRESE, JC
    JONES, NL
    CARROLL, PJ
    BUNEL, EE
    MILLER, JS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (23) : 6182 - 6193
  • [36] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS
    MARYANOFF, BE
    REITZ, AB
    [J]. CHEMICAL REVIEWS, 1989, 89 (04) : 863 - 927
  • [37] CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM
    MCMURRY, JE
    [J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1513 - 1524
  • [38] TITANIUM-INDUCED DICARBONYL-COUPLING REACTIONS
    MCMURRY, JE
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (11) : 405 - 411
  • [39] A SIMPLE SYNTHESIS OF METALLOCENE ALDEHYDES FROM LITHIOMETALLOCENES AND N,N-DIMETHYLFORMAMIDE - FERROCENE AND RUTHENOCENE ALDEHYDES AND 1,1'-DIALDEHYDES
    MUELLERWESTERHOFF, UT
    YANG, Z
    INGRAM, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 463 (1-2) : 163 - 167
  • [40] Intermolecular electron-transfer reactions involving hydrazines
    Nelsen, SF
    Chen, LJ
    Ramm, MT
    Voy, GT
    Powell, DR
    Accola, MA
    Seehafer, TR
    Sabelko, JJ
    Pladziewicz, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) : 1405 - 1412