Multichromophoric polyphenylene dendrimers:: Toward brilliant light emitters with an increased number of fluorophores

被引:62
作者
Oesterling, Ingo [1 ]
Muellen, Klaus [1 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
关键词
D O I
10.1021/ja067174m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two routes for the introduction of highly fluorescent peryleneimide chromophores into the scaffolding of polyphenylene dendrimers via iterative Diels-Alder cycloadditions are presented. The key intermediates for the divergent dendrimer buildup were two cyclopentadienone branching units carrying two peryleneimides and two masked terminal alkynes. The difference between the two reagents is the mode of incorporation of the chromophores. In the first case, the chromophores were attached to the alpha-position of the tetraphenylcyclopentadienones. In the second case, peryleneimides are used as a "spacer" in the beta-position of the cyclopentadienones giving rise to dendrimers with extended molecular diameters (up to 12 nm) and 24 chromophores within their scaffold. Absorption and emission characteristics of the new multichromophoric nanoparticles were investigated and compared to those of the parent dyes. Additionally, an asymmetrically substituted first-generation dendrimer with six perylene diimide chromophores and one ester functionality is reported. The ester serves as a potential anchor group, and this nanoemitter paves the way to a multichromophoric fluorescence label. All dendrimers have good solubility in common organic solvents, high fluorescence quantum yields, and defined distances between the chromophores, making them attractive candidates for single-molecule spectroscopy.
引用
收藏
页码:4595 / 4605
页数:11
相关论文
共 62 条
  • [1] Pushing the synthetic limit:: Polyphenylene dendrimers with "exploded" branching units -: 22-nm-diameter, monodisperse, stiff macromolecules
    Andreitchenko, EV
    Clark, CG
    Bauer, RE
    Lieser, G
    Müllen, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (39) : 6348 - 6354
  • [2] [Anonymous], 2001, DENDRIMERS OTHER DEN
  • [3] Luminescent dendrimers. Recent advances
    Balzani, V
    Ceroni, P
    Maestri, M
    Saudan, C
    Vicinelli, V
    [J]. DENDRIMERS V: FUNCTIONAL AND HYPERBRANCHED BUILDING BLOCKS, PHOTOPHYSICAL PROPERTIES, APPLICATIONS IN MATERIALS AND LIFE SCIENCES, 2003, 228 : 159 - 191
  • [4] SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES
    CASSAR, L
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) : 253 - 257
  • [5] Choi MS, 2001, ANGEW CHEM INT EDIT, V40, P3194, DOI 10.1002/1521-3773(20010903)40:17<3194::AID-ANIE3194>3.0.CO
  • [6] 2-5
  • [7] Frequency selective excitation of single chromophores within shape-persistent multichromophoric dendrimers
    Christ, T
    Kulzer, F
    Weil, T
    Müllen, K
    Basché, T
    [J]. CHEMICAL PHYSICS LETTERS, 2003, 372 (5-6) : 878 - 885
  • [8] Downhill energy transfer via ordered multichromophores in light-harvesting capsules
    Dai, ZF
    Dähne, L
    Donath, E
    Möhwald, H
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (44) : 11501 - 11508
  • [9] Femtosecond fluorescence upconversion study of rigid dendrimers containing peryleneimide chromophores at the rim
    De Belder, G
    Jordens, S
    Lor, M
    Schweitzer, G
    De, R
    Weil, T
    Herrmann, A
    Wiesler, UK
    Müllen, K
    De Schryver, FC
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2001, 145 (1-2) : 61 - 70
  • [10] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES
    DIECK, HA
    HECK, FR
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) : 259 - 263