摘要/Abstract

环八四噻吩（COTh）是一类新发现的具有聚集诱导发光（AIE）特性的"马鞍型"分子.将发光基团芘引入到COTh分子骨架，设计合成了三种芘-环八四噻吩化合物，即单芘基环八四噻吩（Py-COTh）、四芘基环八四噻吩（4Py-COTh）以及四（三（三甲硅基）环八四噻吩基）芘（12TMS-4COTh-Py）.考察了它们的吸收光谱、溶液态与冻结态（77 K）下的荧光光谱以及聚集诱导发光（AIE）行为.研究发现COTh分子骨架上芘基数量的增加对分子的共轭效应影响较小，但其单分子与聚集态的发光行为显著增强且发光峰位红移；而芘基骨架上COTh基团数量的增加，增加了分子的共轭效应，造成了吸收光谱与荧光发射光谱峰位的大范围红移.这些光物理现象与分子结构存在着显著的构效关系.
关键词: 环八四噻吩, 芘, 衍生物合成, 吸收光谱, 荧光光谱, 聚集诱导发光, 构效关系
Cyclooctatetrathiophene (COTh) is a saddle-typed molecule with the interesting property of aggregation induced emission (AIE) discovered recently. In this paper, pyrene was introduced to the framework of COTh as a luminescent group. Three pyrene-COTh derivatives, mono-pyrene substituted COTh (Py-COTh), tetra-pyrene substituted COTh (4Py-COTh) and tetra(tri(trimethylsilyl)cyclooctatetrathiophenyl)pyrene (12TMS-4COTh-Py) were designed and synthesized. Their absorption spectra, fluorescene emission behaviors in solution, rigid state (77 K) and the aggregation state were explored. On the one hand, with increasing pyrene group to the framework of COTh, the molecular conjugation of pyrene-COTh derivatives, Py-COTh and 4Py-COTh changed slightly, but their emission intensity increased heavily with large red shift in both dilute solution and aggregation state. On the other hand, with the increase of COTh group to the framework of pyrene, the molecular conjugation of pyrene-COTh derivatives, Py-COTh and 12TMS-4COTh-Py changed significantly, and their emission intensity increased remarkably with large red shift in dilute solution. The relationship between the photophysical property and molecular structure is remarkably exhibited in our case.
Key words: cyclooctatetrathiophene, pyrene, synthesis of derivative, absorption spectrum, fluorescence spectrum, aggregation induced emission, structure-activity relationship


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