刚-柔嵌段两亲性分子因其分子固有的微相分离作用，在本体及溶液中极易形成分子聚集体，应用于分子识别、传感及功能软材料等领域。本文引入萘单元作为电子供体，萘二酰亚胺（NDI）单元作为电子受体，设计并合成了刚-柔嵌段两亲性分子NAPH-CHO、NDI-OH。利用核磁共振氢谱（¹H NMR）、质谱(MALDI-TOF-MS)、荧光发射光谱（FL）、紫外吸收光谱（UV）、原子力显微镜（AFM）、透射电子显微镜（TEM）等手段分别分析了两种化合物的结构和在水与四氢呋喃的混合体系中的分子的自组装行为及其基于电荷转移相互作用力驱动的化合物的共组装行为。NAPH-CHO和NDI-OH在溶液体系中受到非共价作用力协同驱动分别自组装成纳米片装结构，而二者混合后产生的供体受体相互作用促使其组装成多层片状结构。此外，化合物NAPH-CHO末端的醛基能够与氨基化合物之间形成亚胺键得到化合物PN和BN，利用红外光谱（IR）对亚胺键的形成进行表征，分析不同pH反应体系对其缩合反应的影响及其产物的自组装行为，考察结构变化对电荷转移能力以及形貌的影响。

基于联苯单元设计并合成了三种AB型刚-柔两亲分子CP3、CP4和AP4，和三种ABA型刚-柔两亲分子CP51、CP52、CP53。利用小角x射线散射图谱（SAXS）、差示量热扫描曲线图（DSC）、偏光显微镜（POM）等手段探究了化合物CP4的液晶性质。结果表明化合物CP3由π-π堆积作用和亲疏水作用在水溶液中聚集自组装成超分子纳米片状结构，由于化合物CP4在化合物CP3的基础上增加一个苯单元，使得疏水部分增加，形成了尺寸更大的纳米片状；化合物AP4与CP4具有相同的刚性骨架，而柔性链部分缺少侧链甲基，使化合物AP4的自组装排列结构更紧密，形成了较化合物CP4尺寸更大的超分子纳米片状聚集体。化合物CP51、CP52和CP53具有相同刚性骨架，其中化合物CP51和CP52具有相同的柔性链，但共价连接的柔性部分的数量不同导致化合物CP51形成超分子纳米片状结构，而柔性部分多的化合物CP52组装为纳米纤维结构，化合物中柔性部分横截面积最大的CP53组装成纳米线结构。

Due to its inherent microphase separation effect, rigid flexible amphiphilic molecules are prone to form molecular aggregates in bulk and solution, and are applied in fields, such as molecular recognition, sensing, and functional soft materials. This thesis, two types of rod-coil molecules were designed and synthesized by introducing naphthalene unit as electron donor (NAPH-CHO) and NDI unit as electron acceptor (NDI-OH). The self-assembly behavior of the two compounds in a mixed system of H₂O/THF (v/v=1:9) and the co-assembly behavior of the compounds driven by charge transfer interactions in H₂O and THF solution were studied using nuclear magnetic resonance hydrogen spectroscopy (¹H NMR), mass spectrometry (MALDI-TOF-MS), fluorescence emission spectroscopy (FL), ultraviolet absorption spectroscopy (UV), atomic force microscopy (AFM), and transmission electron microscopy (TEM), respectively. NAPH-CHO and NDI-OH are synergistically driven by non-covalent forces in a solution system to self-assemble into nanosheet structures, respectively. The donor acceptor interaction generated by their mixture promotes the assembly of the mixture into multi-layer sheet-like structures. In addition, the aldehyde group at the end of compound NAPH-CHO can form imine bonds with amino compounds to obtain compounds PN and BN. The formation of imine bonds was characterized by infrared spectroscopy (IR), and the effects of different pH reaction systems on the condensation reaction and the self-assembly behavior of the products were analyzed, and the effects of structural changes on the charge transfer ability and morphology were investigated.

Three AB type rigid flexible amphiphilic molecules CP3, CP4, and AP4, as well as three ABA type rigid flexible amphiphilic molecules CP51, CP52, and CP53, were designed and synthesized based on the biphenyl unit. The liquid crystal properties of the compounds CP4 were investigated using small angle X-ray scattering (SAXS), differential scanning calorimetry (DSC), polarizing microscopy (POM), and other methods. The results showed that compound CP3 aggregates and self-assembles into supramolecular nanosheets in aqueous solution through π-π stacking and hydrophobic interactions. Due to the presence of one more benzene unit in compound CP4 compared to compound CP3, the hydrophobic portion increases, resulting in the formation of larger nanosheets. Compound AP4 and CP4 have the same rigid skeleton, while the flexible chain lacks side chain groups, resulting in a more compact self-assembly structure of compound AP4, forming larger supramolecular nanosheets than compound CP4. Compounds CP51, CP52, and CP53 have the same rigid skeleton, among which compounds CP51 and CP52 have the same flexible chain, but the number of covalently connected flexible parts is different, resulting in the formation of supramolecular nanosheets in compound CP51. Compound CP52 with more flexible parts is assembled into a nanofiber structure, while compound CP53 with the largest cross-sectional area of the flexible part is assembled into a nanowire structure.

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