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Two-Dimensional Nanostructures by the Assembly of n-Type Tetraazaanthracene-Based Conjugated Molecules

Authors

  • Chunyang He,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)
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  • Prof. Dongqing Wu,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)
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  • Prof. Fan Zhang,

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)
    • School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)

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  • Prof. Minzhao Xue,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)
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  • Dr. Xiaodong Zhuang,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)
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  • Dr. Feng Qiu,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)
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  • Prof. Xinliang Feng

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)
    2. Max-Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz (Germany)
    • School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China)

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Abstract

On the basis of our previous communication concerning a new family of thiophene-armed tetraazaanthracene molecules, we present a further intensive investigation on this class of compounds substituted with different alkyl chains and their self-assembled two-dimensional (2D) nanostructures. These tetraazaanthracene molecules with different alkyl chains were prepared in good yields using the synthetic strategy we developed. In addition to the expected typical n-type character, one compound exhibited aggregation behavior upon electrochemical reduction. Moreover, all molecules in the neutral state showed a strong tendency to aggregate in a binary solvent, as confirmed by optical spectral measurements. To investigate such self-assembly behavior, a phase-transfer method with a dichloromethane/methanol (2:3) binary solvent system was used to prepare the nanostructures. By means of atomic force microscopy, transmission electron microscopy, and X-ray diffraction, we found that the morphology of assembled 2D sheet-like structures could be adjusted by varying the alkyl chain. The weak interactions arising from the heteroatoms (N and S) in the conjugated backbones play a key role in the formation and stabilization of layered structures.

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