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首页> 外文期刊>Chemistry: A European journal >Supramolecular Nanowires from an Acceptor–Donor–Acceptor Conjugated Chromophore
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Supramolecular Nanowires from an Acceptor–Donor–Acceptor Conjugated Chromophore

机译：来自受体 - 供体 - 受体缀合发色团的超分子纳米线

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摘要

Oligothiophene derivatives have been extensively studied as p-type semiconducting materials in organic electronics applications. This work reports the synthesis, self-assembly and photophysical properties of acceptor–donor–acceptor (A–D–A)-type oligothiophene derivatives by endgroup engineering of quaterthiophene (QT) with naphthalene monoimide (NMI) chromophores that are further connected to a trialkoxy benzamide wedge. Conjugation to the NMI units reduces the HOMO–LUMO gap significantly, and consequently the absorption spectrum exhibits a bathochromic shift of about 50 nm compared with QT. Furthermore, extended H-bonding interactions among the amido groups of the peripheral wedges produce entangled fibrillar nanostructures and gelation in hydrocarbon solvents such as methylcyclohexane, wherein the A–D–A chromophore exhibits typical H-aggregation. On the contrary, the fact that the same chromophore, lacking only the amido units, does not produce gels or H-aggregates indicates strong impact of Hbonding on the self-assembly. Computational studies revealed the electronic properties of the chromophore and predicted the geometry of a dimer in the H-aggregate that reasonably matches with the experimental results. Bulk electrical conductivity measurements determined an excellent conductivity of 2.3×10~(-2) Scm~(-1) for the H-aggregated system (OT-1), which is two orders of magnitude higher than that of the same chromophore lacking the amido groups (OT-2).
机译：已经在有机电子应用中广泛地研究了低噻吩衍生物作为p型半导体材料。该工作报告了受体 - 供体 - 受体（A-D-A）型寡核蛋白质衍生物的合成，自组装和光物理性质通过与萘单酰亚胺（NMI）发色团的Quatterthoophene（QT）的嵌合膦植入工程进行了进一步连接到A Trialkoxy Benzamide Wedge。与NMI单元的缀合显着降低了同源叶片间隙，因此吸收光谱与QT相比表现出约50nm的碱基转移。此外，外周楔的酰胺基团之间的延伸的H键合相互作用在烃类溶剂如甲基环己烷中产生缠结的纤维纳米结构和凝胶化，其中A-D-A发色团表现出典型的H聚集。相反，同样发色团仅缺乏酰胺单位，不产生凝胶或H聚集体表明Hbonding对自组装的强烈影响。计算研究揭示了发色团的​​电子性质，并预测了与实验结果合理匹配的H骨料中二聚体的几何形状。散装电导率测量确定H型聚集系统（OT-1）的2.3×10〜（-2）SCM〜（-1）的优异导电率，这是比缺乏相同发色团的两个数量级amido群体（OT-2）。

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