Xu Shaojie, Wang Xiangyu, Zeng Le, Bu Xian-He
School of Materials Science and Engineering, Tianjin Key Laboratory of Metal and Molecule Based Material Chemistry, Nankai University, Tianjin, 300350, P. R. China.
State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, China.
Adv Mater. 2025 Aug 6:e08888. doi: 10.1002/adma.202508888.
Chiral supramolecular architectures based on naphthalene diimide (NDI) and perylene diimide (PDI) possess significant potential for chiroptical applications due to their physical properties, including large molar extinction coefficient, high fluorescence quantum yield, reversible redox activity, and robust photochemical/thermal stability. The chirality of NDI/PDI-based supramolecular architectures primarily originates from three sources: i) covalent modification of NDI/PDI with chiral substituents, ii) intrinsic axial chirality through distortion of the PDI conjugated plane, and iii) supramolecular asymmetric assembly of achiral NDI/PDI induced by exogenous chiral environments. This review systematically outlines recent advancements in the design principles of NDI/PDI-based chiral supramolecular architectures, including macrocycles, cages, aggregates, and crystalline frameworks, with an emphasis on the structure-activity relationship for chirality induction, transmission, and amplification. Advancements for their functional applications in circularly polarized luminescence (CPL), optoelectronic detectors, and asymmetric catalysis are also listed. Despite such progress, challenges persist in expanding the diversity of chiral NDI/PDI motifs, regulating the weak interactions for chiral supramolecular structures, elucidating chirality transfer and amplification mechanisms, and realizing diverse chiral applications. This review provides a comprehensive guide for the rational design of NDI/PDI-based chiral supramolecular architectures, facilitating their full exploitation in next-generation chiral technologies, like CPL light-emitting diode and chiral biomedicine.
基于萘二亚胺（NDI）和苝二亚胺（PDI）的手性超分子结构因其物理性质，包括大的摩尔消光系数、高荧光量子产率、可逆的氧化还原活性以及强大的光化学/热稳定性，在手性光学应用中具有巨大潜力。基于NDI/PDI的超分子结构的手性主要源于三个方面：i）用手性取代基对NDI/PDI进行共价修饰；ii）通过PDI共轭平面的扭曲产生固有轴向手性；iii）由外源性手性环境诱导的非手性NDI/PDI的超分子不对称组装。本综述系统地概述了基于NDI/PDI的手性超分子结构（包括大环、笼状、聚集体和晶体框架）设计原理的最新进展，并重点阐述了手性诱导、传递和放大的构效关系。还列出了它们在圆偏振发光（CPL）、光电探测器和不对称催化等功能应用方面的进展。尽管取得了这些进展，但在扩大手性NDI/PDI基序的多样性、调节手性超分子结构的弱相互作用、阐明手性传递和放大机制以及实现多样化的手性应用方面仍存在挑战。本综述为基于NDI/PDI的手性超分子结构的合理设计提供了全面指导，有助于它们在下一代手性技术（如CPL发光二极管和手性生物医学）中得到充分利用。
