Organic fluorescent semiconducting nanomaterials have gained widespread research interest owing to their potential applications in the arena of high-tech devices. We designed two pyrazaacene-based compounds, their stacked system, and the role of gluing interactions to fabricate nanomaterials, and determined the prospective band gaps utilizing the density functional theory calculation. The two pyrazaacene derivatives containing complementary amide linkages (-CONH and -NHCO) were efficiently synthesized. The synthesized compounds are highly soluble in common organic solvents as well as highly fluorescent and photostable. The heterocycles and their mixture displayed efficient solvent dependent fluorescence in the visible region of the solar spectrum. Notably, the compounds were associated through complementary NH•••O = C type hydrogen bonding, π-π stacking, and hydrophobic interactions, and thereby afforded nanomaterials with a low band gap. Fascinatingly, the fabricated stacked nanomaterial system exhibited resistive switching behavior, leading to the fabrication of an efficient write-once-read-many-times memory device of crossbar structure.

中文翻译：

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互补的基于酰胺的供体-受体，具有独特的纳米级聚集、荧光和带隙降低特性：一种 WORM 存储设备

有机荧光半导体纳米材料因其在高科技设备领域的潜在应用而受到广泛的研究兴趣。我们设计了两种基于吡唑并苯的化合物、它们的堆叠系统以及胶合相互作用在制造纳米材料中的作用，并利用密度泛函理论计算确定了预期的带隙。高效合成了含有互补酰胺键（-CONH 和-NHCO）的两种吡唑并苯衍生物。合成的化合物高度可溶于普通有机溶剂，并具有高荧光性和光稳定性。杂环化合物及其混合物在太阳光谱的可见区域显示出有效的溶剂依赖性荧光。值得注意的是，这些化合物通过互补的 NH•••O = C 型氢键结合，π-π堆叠和疏水相互作用，从而提供具有低带隙的纳米材料。令人着迷的是，制造的堆叠纳米材料系统表现出电阻开关行为，从而制造出高效的一次写入多次读取的交叉结构存储设备。