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基于氢键和两亲性组装的光开关超分子的设计合成及应用
【作者】 张松；
【作者基本信息】 上海师范大学 ， 无机化学， 2011， 硕士
【摘要】 由功能性小分子组装成具有超分子结构的软材料和纳米器件是一种有效的发展新材料的方法,近些年来新型的超分子自组装材料构筑模块已经越来越引起人们的注意。因为它们可以通过特殊的非化学键分子相互作用如氢键,疏水作用,π-π堆积作用及范德华力来形成具有稳定均一结构的纳米级器件。本文中,我们采用光致变色二芳乙烯分子通过接有萘啶的衍生物来达到识别含有萘酰亚胺的鸟嘌呤衍生物的作用,对形成组装的机理,组装的形貌,以及堆积形式加以研究,同时将该材料应用于生物成像,发现其在不同比例组装下对KB细胞有特别的作用,同时还设计合成了一些预期小分子凝胶中间体,本文结构如下:1.设计了含有萘啶的二芳烯衍生物,通过强的三重氢键作用与含有萘酰亚胺荧光团的鸟嘌呤衍生物进行氢键组装,通过核磁滴定和光谱数据证实了组装行为,通过扫描电镜观察了组装后的形貌。组装体含有特殊的光物理光化学性质,以及相应的光致变色行为,不同比例的组装体对于KB细胞有特殊的作用,与HeLa细胞进行了比对试验2.设计合成了含有胆甾酸的的伞形分子,没有获得预期的凝胶效果,发现胆甾酸衍生物几乎不能形成有机凝胶,合成了含有没食子酸长烷基链衍生物的预期小分子凝胶中间体,对比分子进行了合成设计表征。
【Abstract】 The self-assembling of small functional molecules into supramolecular structures is a powerful approach towards the development of soft materials and nanoscale devices. As a novel class of self-assembled materials, new supramolecular building block have received considerable attention in recent years because they can organize into regular nanoarchitectures through specific non-covalent interactions including hydrogen-bonding, hydrophobic interactions,π-πinteractions and Van der Waals forces. In this masters thesis, photochromic diarylethene moiety contained naphthyridine and the derivative of guanine were designed and synthesized. The morphology, mechanism of the assembly formation and the packing fashion were studied in details, and the assembly materials were applied in bio-imaging,and respond to KB cell. Meanwhile, some low weight molecular gelator synthetized. The research contains two parts as following1. strong intermolecular hydrogen-bonds are designed through naphthyridine and guanine base on diarylethene, which are verified by NMR,UV-VIS,IR, The self-assembly complex gives special photophysical and photochemical properties and these properties could be well controlled by light.The complex can imagine in KB cell ,different proportions can get different results.2. We synthesized derivatives of cholic acid with naphthalimide and found that the small amount of low weight molecules can not gel any organic solvents. Designed and synthesized two derivatives of trihydroxybenzoic with three hydrophobic alkyl chains , which have the ability for gelating some organic solvents.