Hartmann Denis, Penty Samuel E, Zwijnenburg Martijn A, Pal Robert, Barendt Timothy A
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, United Kingdom.
Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, United Kingdom.
Angew Chem Int Ed Engl. 2025 Apr 7;64(15):e202501122. doi: 10.1002/anie.202501122. Epub 2025 Feb 10.
Helical assemblies of organic dyes are ubiquitous chiral organic materials, with valuable properties including chiroptical switching due to the dynamic nature of supramolecular chirality. Herein, we report a novel chiral bis-perylene diimide macrocycle, which acts as a discrete molecular model for a chiral supramolecular assembly. Point chirality is installed through amino acid-derived imide groups which, upon macrocyclization, is translated into helical chirality in the perylene diimide dimer. In solution, the macrocycle's chiroptical properties are switchable, with both the sign (+/-) and amplitude (on/off) of the signal tuned using solvent and molecular recognition stimuli respectively. The chiral structure-property relationships identified from this macrocycle are important for the design of high fidelity supramolecular chiroptical switches.
有机染料的螺旋组装体是普遍存在的手性有机材料，具有宝贵的特性，包括由于超分子手性的动态性质而产生的手性光开关效应。在此，我们报道了一种新型手性双苝二酰亚胺大环化合物，它作为手性超分子组装体的离散分子模型。通过氨基酸衍生的酰亚胺基团引入点手性，在大环化后，该点手性转化为苝二酰亚胺二聚体中的螺旋手性。在溶液中，大环化合物的手性光性质是可切换的，信号的符号（+/-）和幅度（开/关）分别通过溶剂和分子识别刺激进行调节。从该大环化合物中确定的手性结构-性质关系对于高保真超分子手性光开关的设计很重要。
