6 research outputs found

    1,6- and 2,7-<i>trans</i>-β-Styryl Substituted Pyrenes Exhibiting Both Emissive and Semiconducting Properties in the Solid State

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    Molecular materials that are both emissive and semiconducting are highly demanding for organic optoelectronics. In this article, we report the synthesis, emissive, and semiconducting properties of 1,6 and 2,7-<i>trans</i>-β-styryl substituted pyrenes (<b>16PyE</b> and <b>27PyE</b>). The results reveal that both <b>16PyE</b> and <b>27PyE</b> are emissive and semiconducting in the solid state. The fluorescence quantum yields of crystalline solids of <b>16PyE</b> and <b>27PyE</b> were determined to be 28.8% and 27.4%, respectively. Microrods of <b>16PyE</b> and microplates of <b>27PyE</b> were found to exhibit promising optical waveguilding behavior. Furthermore, on the basis of the transfer and output curves of the respective organic field effect transistors (OFETs), thin films of <b>16PyE</b> and <b>27PyE</b> were found to show <i>p</i>-type semiconducting properties with hole mobility up to 1.66 cm<sup>2</sup>V<sup>–1</sup>s<sup>–1</sup>. Such dual functions (emissive and semiconducting) of <b>16PyE</b> and <b>27PyE</b> can be ascribed to the unique intermolecular interactions and packing within crystals of <b>16PyE</b> and <b>27PyE</b>. Both 1,6 and 2,7-<i>trans</i>-β-styryl substituted pyrenes show relatively strong emissions in the solid state, and their microcrystalline samples exhibit promising optical waveguilding behavior. Moreover, their thin films exhibit <i>p</i>-type semiconducting property with hole mobilities up to 1.66 cm<sup>2</sup>V<sup>–1</sup>s<sup>–1</sup>

    Spiro-Fused Perylene Diimide Arrays

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    The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C–H activations and 4-fold C–C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (<b>NDP</b>) and further π-extended spiro system (<b>SNTP</b>). In addition, the molecular structure of spirodiperylenetetraimide (<b>SDP</b>) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells

    Spiro-Fused Perylene Diimide Arrays

    No full text
    The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C–H activations and 4-fold C–C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (<b>NDP</b>) and further π-extended spiro system (<b>SNTP</b>). In addition, the molecular structure of spirodiperylenetetraimide (<b>SDP</b>) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells

    Fullerene/Sulfur-Bridged Annulene Cocrystals: Two-Dimensional Segregated Heterojunctions with Ambipolar Transport Properties and Photoresponsivity

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    Fullerene/sulfur-bridged annulene cocrystals with a two-dimensional segregated alternating layer structure were prepared by a simple solution process. Single-crystal analysis revealed the existence of continuing π–π interactions in both the donor and acceptor layers, which serve as transport paths for holes and electrons separately. The ambipolar transport behaviors were demonstrated with single-crystal field-effect transistors and rationalized by quantum calculations. Meanwhile, preliminary photoresponsivity was observed with the transistor configuration

    Fullerene/Sulfur-Bridged Annulene Cocrystals: Two-Dimensional Segregated Heterojunctions with Ambipolar Transport Properties and Photoresponsivity

    No full text
    Fullerene/sulfur-bridged annulene cocrystals with a two-dimensional segregated alternating layer structure were prepared by a simple solution process. Single-crystal analysis revealed the existence of continuing π–π interactions in both the donor and acceptor layers, which serve as transport paths for holes and electrons separately. The ambipolar transport behaviors were demonstrated with single-crystal field-effect transistors and rationalized by quantum calculations. Meanwhile, preliminary photoresponsivity was observed with the transistor configuration
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