Chiral assembly of organic luminogens with aggregation-induced emission

Liu, Chenchen; Yang, Juncheng; Lam, Jacky W. Y.; Feng, Hai-Tao; Tang, Ben Zhong

doi:10.1039/d1sc02305e

Cited by 90 publications

(57 citation statements)

References 99 publications

(153 reference statements)

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“…Chiral organic molecules exhibiting CPL property, with both a large g lum value and a high luminescence efficiency, are highly desired due to their potential applications in the wide range of 3D optical displays, encryptions, biological probes, chiral photoelectric devices, and CPL switches. From the viewpoint of practical application, it is imperative to develop solid-state CPL materials while maintaining a high luminescence efficiency [42][43][44]. Unfortunately, π-conjugated luminophores always face a general situation of aggregationcaused quenching (ACQ) of luminescence effect in their aggregate or assembly state (Figure 5a), which dramatically deteriorates the CPL performance [45,46].…”

Section: Cpl From Aie-active Aggregatesmentioning

confidence: 99%

Frontiers in circularly polarized luminescence: molecular design, self-assembly, nanomaterials, and applications

et al. 2021

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The research in circularly polarized luminescence has attracted wide interest in recent years. Efforts on one side are directed toward the development of chiral materials with both high luminescence efficiency and dissymmetry factors, and on the other side, are focused on the exploitations of these materials in optoelectronic applications. This review summarizes the recent frontiers (mostly within five years) in the research in circularly polarized luminescence, including the development of chiral emissive materials based on organic small molecules, compounds with aggregation-induced emissions, supramolecular assemblies, liquid crystals and liquids, polymers, metal-ligand coordination complexes and assemblies, metal clusters, inorganic nanomaterials, and photon upconversion systems. In addition, recent applications of related materials in organic light-emitting devices, circularly polarized light detectors, and organic lasers and displays are also discussed.

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Section: Cpl From Aie-active Aggregatesmentioning

confidence: 99%

Frontiers in circularly polarized luminescence: molecular design, self-assembly, nanomaterials, and applications

et al. 2021

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“…A number of chiral or achiral AIEgen have been developed for the purpose of constructing chiral assemblies, and there are some CPL emitters based on the macrocyclic AIEgen with tetraphenylethylene (TPE) unit have been reported. [84][85][86] Zheng and co-workers synthesized propeller-like tetracyclic TPE 40, whose phenyl rings are immobilized by tethering linkers (Figure 28). [87] The fixed conformers are separated into Pand M-isomers exhibiting chiroptical properties.…”

Section: Chiral Assembly Of Tpe Macrocyclesmentioning

confidence: 99%

Circularly Polarized Luminescence in Chiral π‐Conjugated Macrocycles

2021

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Dedicated to Prof. Masahiko Iyoda on the occasion of his 75 th birthday.The design and synthesis of novel π-conjugated macrocycles have been an attractive topic in synthetic chemistry and material and supramolecular chemistry. The distortion caused by the strain of the rigid cyclic structure confers an intrinsic chirality to the π-conjugated unit without a chiral center. In addition, due to the cyclic arrangement of multiple πconjugated units through the stereogenic elements, macrocyclic compounds have a configurationally stable symmetrical structure. They usually impart intensive circularly polarized luminescence (CPL) properties, and some of them exhibit outstanding dissymmetry factor (j g lum j > 0.1) for a simple organic molecule. This Minireview offers the first overview of a various range of CPL emitters based on chiral macrocycles. A focus is given to the relationship between molecular structure, symmetry, and CPL properties, derived from electric and magnetic transition dipole moments. It is hoped that this review will boost to the development of functional materials of these exotic organic CPL emitters.

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“…However, things will be different at the aggregate level as achiral molecules can also form chiral substances through aggregation. 28,36 The tetraphenyethylene (TPE) molecule is an achiral racemic mixture in the monodisperse solution state; however, the crystallization process can induce the spontaneous resolution of the racemers to form two kinds of crystals in which clockwise-oriented (M-TPE) and anticlockwise-oriented (P-TPE) TPEs with optical activity were formed (Figure 2a). 30 Circular dichroism (CD) spectra confirmed the mirror symmetry characteristic of M-TPE and P-TPE.…”

Section: Aggregate Chiralitymentioning

confidence: 99%

“…On the base of AIE, new branches including crystallization-induced emission (CIE), room-temperature phosphorescence (RTP), aggregation-induced delayed fluorescence (AIDF), anti-Kasha transition (AKT), clusterization-triggered emission (CTE), through-space interaction (TSI), mechanoluminescence (ML), circularly polarized luminescence (CPL), photothermal/photoacoustic (PT/PA), and solid-state molecular motion (SSMM) have been developed. Apart from luminescence, aggregation has also been found to benefit intersystem crossing (ISC), triplet-state stabilization, reactive oxygen species (ROS) generation, chiral assembly, and molecular microenvironment tuning . Therefore, research on aggregate structure, properties, and behavior is growing as a new kind of science, which is aggregate science.…”

Section: Introductionmentioning

confidence: 99%

Aggregate Materials beyond AIEgens

Zhao

Tang

2021

Acc. Mater. Res.

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Metrics & MoreArticle RecommendationsCONSPECTUS: Aggregate materials focus on the materials that are constituted by more than a single entity. It could be dimers, trimers, or multimers formed by the group of same molecules or mixtures formed by different molecules. Although materials have different forms such as liquid, hydrogel, colloidal suspension, and powder, aggregates undisputedly are among the most commonly existing forms, which involve many aspects of human daily life such as the clothes we wear, the drugs we take, the food we eat, and the tools and devices we use. Sciences related to aggregate materials are also rich. From molecules to aggregates, different aspects of science such as crystallography, interfacial science, supramolecular science, and engineering science may be involved. Therefore, research on aggregate materials and related mechanisms that dominate the properties of aggregate materials is significant. However, it is noteworthy that reductionism is the dominant research philosophy for the design of traditional materials, and it claims that a molecule is the smallest particle of a substance that retains all of the properties of the substance. Consequently, scientists have expended a lot of effort to develop new molecules and to study the relationships between molecular structure and properties without paying attention to aggregate tuning. Actually, more and more research supports the fact that aggregate control such as the tuning of the packing mode, self-assembly, and morphology could work as a more versatile and effective strategy to endow materials with rich properties and functions. A prototype of the aggregate research is the aggregation-induced emission (AIE) phenomenon and materials. AIE research mainly focuses on the luminescence change accompanied by the aggregation process. After more than 20 years of flourishing development, AIE research has made great advances in new material development, mechanism studies, and hightechnology applications. More importantly, AIE research opens the window to aggregate science and demonstrates that new behaviors and functions that are absent in single molecular species can be generated in molecular aggregates.In this Account, we highlight our efforts toward aggregate materials beyond AIE luminogens (AIEgens), with a special focus on new properties in addition to luminesce endowed by aggregation. We first summarize the chirality that is induced by the aggregation process of prochiral molecules. Then we present the aggregation resulting from the transformation between hydrophilicity and hydrophobicity. After that, the aggregation-induced generation of reactive oxygen species (ROS) is described and the regulation of the aggregation state for tuning the ROS generation efficiency is discussed. We also discuss how to achieve the switch between radiative decay and nonradiative decay through the regulation of the aggregation extent to afford luminescence and photothermy (photothermal effect), respectively. Additionally, different strategies to accelerate th...

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Chiral assembly of organic luminogens with aggregation-induced emission

Abstract: This review highlights the recent development of chiral materials with aggregation-induced emission properties, including their molecular structures, self-assembly and functions.

Cited by 90 publications

References 99 publications

Frontiers in circularly polarized luminescence: molecular design, self-assembly, nanomaterials, and applications

Frontiers in circularly polarized luminescence: molecular design, self-assembly, nanomaterials, and applications

Circularly Polarized Luminescence in Chiral π‐Conjugated Macrocycles

Aggregate Materials beyond AIEgens

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