Synthesis, structure, and optical properties of terminally sulfur-functionalized core-substituted naphthalene-bisimide dyes

被引:39
作者
Blaszczyk, Alfred
Fischer, Matthias
von Haenisch, Carsten
Mayor, Marcel
机构
[1] Forschungszentrum Karlsruhe, Inst Nanotechnol, D-76021 Karlsruhe, Germany
[2] Fac Commod Sci, PL-60967 Poznan, Poland
[3] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
关键词
D O I
10.1002/hlca.200690190
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis, characterization, and optical properties of a series of new 2,6-disubstituted naphthalene-bisimide dyes as molecular rods comprising terminal AcS groups is reported. The first series of dyes (1-3), comprising phenylhetero (Ph-X) core substituents, cover a broad range of the VIS spectrum, ranging from yellow (2) over red (3) to blue (1). The second series of dyes contains benzylhetero (Bn-X) core substituents (4-7). For the same heteroatom connecting the substituent to the naphthalene core, both series were found to display comparable colors. For the second series, the colors were blue (4), red (5), and violet (6, 7). The Ph-X-substituted dyes 1-3 are nonfluorescent, in contrast to the Bn-X-substituted compounds 4-7. This rich variety of optical features that can be adjusted by rather small alterations of the core substituents makes these structurally very comparable molecular rods ideal candidates for optically triggered molecular-transport investigations. Also, thanks to the terminal AcS groups, these compounds can be placed between nobel-metal electrodes for optically triggered transport experiments.
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收藏
页码:1986 / 2005
页数:20
相关论文
共 43 条
  • [1] CONFORMATIONAL ANALYSIS .51. CONFORMATIONS OF CYCLOHEXANONE RINGS IN SIMPLE MOLECULES
    ALLINGER, NL
    BLATTER, HM
    FREIBERG, LA
    KARKOWSK.FM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (13) : 2999 - &
  • [2] Becker H. G. O., 2001, ORGANIKUM ORGANISCH, P741
  • [3] Bromine catalyzed conversion of S-tert-butyl groups into versatile and, for self-assembly processes accessible, acetyl-protected thiols
    Blaszczyk, A
    Elbing, M
    Mayor, M
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) : 2722 - 2724
  • [4] Reproducible measurement of single-molecule conductivity
    Cui, XD
    Primak, A
    Zarate, X
    Tomfohr, J
    Sankey, OF
    Moore, AL
    Moore, TA
    Gust, D
    Harris, G
    Lindsay, SM
    [J]. SCIENCE, 2001, 294 (5542) : 571 - 574
  • [5] ELECTRONIC EFFECTS OF SULPHUR IN FIRST FEW EXCITED STATES OF AROMATIC SULPHIDES
    DEGANI, J
    MANGINI, A
    TROMBETTI, A
    ZAULI, C
    [J]. SPECTROCHIMICA ACTA PART A-MOLECULAR SPECTROSCOPY, 1967, A 23 (05): : 1351 - +
  • [6] One-way optoelectronic switching of photochromic molecules on gold
    Dulic, D
    van der Molen, SJ
    Kudernac, T
    Jonkman, HT
    de Jong, JJD
    Bowden, TN
    van Esch, J
    Feringa, BL
    van Wees, BJ
    [J]. PHYSICAL REVIEW LETTERS, 2003, 91 (20)
  • [7] A single-molecule diode
    Elbing, M
    Ochs, R
    Koentopp, M
    Fischer, M
    von Hänisch, C
    Weigend, F
    Evers, F
    Weber, HB
    Mayor, M
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (25) : 8815 - 8820
  • [8] Diode-like electron transfer across nanostructured films containing a redox ligand
    Gittins, DI
    Bethell, D
    Nichols, RJ
    Schiffrin, DJ
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2000, 10 (01) : 79 - 83
  • [9] GUNTHER WHH, 1967, J ORG CHEM, V32, P3929