Naphthalene- and Perylene-Diimide-Based Chiral Supramolecular Architectures

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.