Design, synthesis and characterization of novel (2S)-2-[7-(2-aminoethyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydrobenzo[lmn][3,8]phenanthrolin-2(1H)-yl]propanoic acid (1) bolaamphiphile, which combine naphthalene diimide (NDI) appended with l-alanine at one end of imide and ethylenediamine at the other end. An l-alanine bearing NDI-based asymmetric bolaamphiphile self-assembled at various pH ranging from 2 to 10 forms a variety of supramolecular nanostructures. The UV-Vis and emission spectroscopic techniques employed for the optical and photophysical properties study of bolaamphiphile 1 at various pH values. It was revealed that the change in pH alters both the optical and photophysical properties of bolaamphiphile 1. Theoretical calculations used to investigate the electronic properties of the bolaamphiphile 1. Dynamic light scattering experiments displayed formation of aggregates in solution and scanning electron microscopy (SEM) was used to visualize the nanostructures formed on silicon wafers. Furthermore, the X-ray diffraction was used to determine the nanostructure's packing properties i. e. crystalline/amorphous. Experimental circular dichroism (CD) spectroscopy results inferred and revealed the induction of chirality into the supramolecular systems, which was shown to be pH dependent. This study clearly demonstrates the manipulation of pH can control/tune chiral supramolecular structures and provide future methods for the development of chiral recognition and catalysis study.

中文翻译：

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萘二亚胺附加的 l-丙氨酸和乙二胺不对称 Bolaamphiphile 的 pH 控制超分子自组装

新型 (2 S )-2-[7-(2-氨基乙基)-1,3,6,8-tetraoxo-3,6,7,8-四氢苯并[ lmn ][3,8] 的设计、合成和表征phenanthrolin-2(1 H ) -yl ]propanoic acid ( 1 ) bolaamphiphile，它结合了萘二亚胺(NDI)，在酰亚胺的一端附加了l-丙氨酸，在另一端连接了乙二胺。一升在不同pH范围为2至10形成的各种超分子的纳米结构的基于NDI-丙氨酸轴承不对称bolaamphiphile自组装。紫外-可见分光光度计和发射光谱技术用于研究 bolaamphiphile 1的光学和光物理性质在不同的 pH 值下。结果表明，pH 值的变化会改变 bolaamphiphile 1的光学和光物理特性 。用于研究 bolaamphiphile 1电子特性的理论计算 。动态光散射实验显示在溶液中形成聚集体，并且使用扫描电子显微镜 (SEM) 来可视化在硅晶片上形成的纳米结构。此外，X 射线衍射用于确定纳米结构的堆积特性i。电子. 结晶/无定形。实验圆二色性 (CD) 光谱结果推断并揭示了超分子系统中手性的诱导，这被证明是 pH 依赖性的。这项研究清楚地证明了 pH 值的操纵可以控制/调整手性超分子结构，并为手性识别和催化研究的发展提供未来的方法。