Chirality of Perylene Diimides: Design Strategies and Applications

Abstract

Chirality is a particularly important concept in nature and exists at all length scales, ranging from the molecular level to the supramolecular level. Over the last two decades, various design strategies have been developed to construct chiral materials based on perylene diimides (PDIs) and to mimic the chiral assembly process in biological systems, but applications of these chiral aggregates are still at an early stage. This Minireview summarizes recent progress in the synthesis and properties of chiral PDIs. The chirality in PDI‐based materials can be generated by three different approaches: from the twisted planes of PDIs, the chiral substituents of PDIs, and the co‐assembly of achiral PDIs and chiral guests. A comprehensive understanding of the applications of chiral PDIs as well as potential future developments is also provided.

A persistent radical anion derived from a propeller-shaped perylene bisimide-carbazole pentad

“…Among the reactive radical ions, of special interest is the perylene bisimide (PBI)-based radical anion (PBI˙ − ) featuring strong absorption in the near-infrared (NIR) region, which has been widely utilized as a photocatalyst, 2,11 photothermal material, 12 etc. By virtue of easy modification of PBI scaffolds, 13 PBI˙ − with various structures have been obtained. For example, Würthner et al invented a straightforward synthetic procedure for the isolation of the first ambient stable PBI˙ − and PBI 2− using highly electron-deficient PBI molecules.…”

Structures and Applications of NIR‐II AIEgens Containing Benzobisthiadiazole Derivatives

“…[53] Compared with serological diagnosis required multiple biomarkers for detection, the precise fluorescence imaging mode technology of tumors has been greatly developed in recent years. [54][55] Traditional fluorescent organic dyes used for imaging usually exhibit wide emission band and narrow excitation wavelength. Inorganic quantum dots are widely used in the fields of biosensors and bioimaging due to their wide excitation range and narrow emission spectrum, better light stability and simple synthesis.…”

“…Currently, the early diagnosis and treatment of tumors were mainly based on serological diagnosis, cytopathological diagnosis, endoscopic diagnosis, ultrasonic diagnosis and imaging diagnosis [53] . Compared with serological diagnosis required multiple biomarkers for detection, the precise fluorescence imaging mode technology of tumors has been greatly developed in recent years [54–55] …”

Perylene‐Mediated Electron Leakage in Respiratory Chain to Trigger Endogenous ROS Burst for Hypoxic Cancer Chemo‐Immunotherapy

“…Perylenediimides (PDIs) have been widely investigated as excellent photoelectric and biomedical materials. [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ] Perylene consists of an electron‐deficient system that could be readily reduced to form a delocalized radical anion. [ 39 , 40 , 41 , 42 ] It should be pointed out that perylene anion is highly sensitive to the oxidizing substance, and thus, easily transfer electrons to ones that promote the formation of endogenous ROS.…”