Controllable aggregation-induced emission based on a tetraphenylethylene-functionalized pillar[5]arene via host–guest recognition

Wu, Jie; Sun, Shengjie; Feng, Xiang; Shi, Jianbing; Hu, Xiao‐Yu; Wang, Leyong

doi:10.1039/c4cc03127j

Cited by 109 publications

(37 citation statements)

References 28 publications

(3 reference statements)

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“…CuAAC reaction of di-and tetra-alkynes with pillar [5]arenes possessing an azide moiety 107 [5] produced a pillar [5]arene dimer 108 [5] and a tetramer. 126,127 The other process for the synthesis of pillar [5]arene dimers is the cocyclization method. Huang et al and Xiao, Jiang et al…”

Section: Functionalization Of Pillar[n]arenes Bearing Phenolic Groupsmentioning

confidence: 99%

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

2016

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In 2008, we reported a new class of pillar-shaped macrocyclic hosts, known as "pillar[n]arenes". Today, pillar[n]arenes are recognized as key players in supramolecular chemistry because of their facile synthesis, unique pillar shape, versatile functionality, interesting host-guest properties, and original supramolecular assembly characteristics, which have resulted in numerous electrochemical and biomedical material applications. In this Review, we have provided historical background to macrocyclic chemistry, followed by a detailed discussion of the fundamental properties of pillar[n]arenes, including their synthesis, structure, and host-guest properties. Furthermore, we have discussed the applications of pillar[n]arenes to materials science, as well as their applications in supramolecular chemistry, in terms of their fundamental properties. Finally, we have described the future perspectives of pillar[n]arene chemistry. We hope that this Review will provide a useful reference for researchers working in the field and inspire discoveries concerning pillar[n]arene chemistry.

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Section: Functionalization Of Pillar[n]arenes Bearing Phenolic Groupsmentioning

confidence: 99%

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

2016

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“…[68] It is known that pillararenes have high affinity toward neutral nitrile moieties. Based on this knowledge,W ang et al [69] designed aT PE-functionalized pillar [5]arene (TPEP5) by attaching four DMPillar [5]arene (DMP5)g roups to the periphery of TPE ( Figure 29). In CH 3 Cl/acetone this molecule is nonemissive.…”

Section: Pillararene-based Small Moleculesmentioning

confidence: 99%

“…a) Schematicillustration of the assembly of the host-guest recognitioncomplex of TPEP5 and G1. [69] b) Changei nfluorescencewith addition of G1 to as olutiono fT PEP5. c) TEM image of the host-guest complex formedb yTPEP5 and G1.…”

Section: Pillararene-based Small Moleculesmentioning

confidence: 99%

Self‐Assembly of Aggregation‐Induced‐Emission Molecules

Huang

Yan

2019

Chemistry An Asian Journal

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The last decade has witnessed rapid developments in aggregation‐induced emission (AIE). In contrast to traditional aggregation, which causes luminescence quenching (ACQ), AIE is a reverse phenomenon that allows robust luminescence to be retained in aggregated and solid states. This makes it possible to fabricate various highly efficient luminescent materials, which opens new paradigms in a number of fields, such as imaging, sensing, medical therapy, light harvesting, light‐emitting devices, and organic electronic devices. Of the various important features of AIE molecules, their self‐assembly behavior is very attractive because the formation of a well‐defined emissive nanostructure may lead to advanced applications in diverse fields. However, due to the nonplanar topology of AIEgens, it is not easy for them to self‐assemble into well‐defined structures. To date, some strategies have been proposed to achieve the self‐assembly of AIEgens. Herein, we summarize the most recent approaches for the self‐assembly of AIE molecules. These approaches can be sorted into two classes: 1) covalent molecular design and 2) noncovalent supramolecular interactions. We hope this will inspire more excellent work in the field of AIE.

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“…Wang and co‐workers functionalized P5 rings onto TPE molecules to obtain a fluorescent crosslinking aggregates mediated by host–guest recognition with suitable guest linkers . The addition of competitive binding agents caused the disassociation of host–guest complex.…”

Section: Aie‐active Supramolecular Nanocomplexes/polymersmentioning

confidence: 99%

Manipulating Aggregation‐Induced Emission with Supramolecular Macrocycles

Lou

Yang

2018

Advanced Optical Materials

116

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host and guest bears excellent selectivity. [5] On the other hand, the noncovalent interactions are sensitive to various influential elements in the surrounding environment, including light irradiation, [6] redox reactions, [7] pH variations, [8] competitive factors, [9] and chemical or biological interfering. [10,11] Owing to the highly desired characteristics of host-guest systems comprising of supramolecular macrocycles and their guests, the dynamic nature of their molecular activities, the reversibility between assembly and disassembly, the particular intermolecular recognition and the responsiveness toward external stimuli, supramolecular host-guest systems become outstanding candidates as building blocks in the construction of nanoscaled smart materials with controllable properties, which are substantial in the research ranges of nanotechnology and materials science. Up till today, a number of host compounds, such as crown ethers, [12,13] cyclodextrins (CDs), [14] calixarenes, [15] cucurbit[n]urils (CB[n]s), [16][17][18] and pillararenes, [19,20] on account of their developed synthetic procedures, relatively high yieldings, numerous modification possibilities and tunability, [21,22] along with their well-explored host-guest properties, [5] have been utilized to construct stimuliresponsive smart materials to serve as either supramolecular recognizing agents or the major building blocks for reversible artificial complexes. [1,23,24] An important use of macrocyclic compounds to create functional smart materials lies in the construction of controllable fluorescent systems. [25] In the literature, one can find considerable examples of fluorescent systems manipulated by supramolecular macrocycles through their distinctive inclusion complexation activities. [26][27][28][29] The concept of aggregation-induced emission (AIE) was first proposed by Tang and co-workers in 2001, [30] demonstrating an unprecedented fluorescent phenomenon, which bears luminescent features in sharp contrast to the traditional aggregation-caused quenching (ACQ) that is typical for conventional organic fluorophores. While the ACQ effect stands as a major hindrance for the solidation of luminescent materials since luminophores with planar molecular structures undergo fluorescence quenching in aggregated state, dye molecules possessing unplanar conformations, on the contrary, are able to exhibit stronger emission upon aggregation according to the restriction of intramolecular motions (RIM) or rotations (RIR), which suppresses nonradiative relaxation and actuates the energy release through radiative pathway. [31,32] Two essential elements of smart materials are their capabilities of responding to external stimuli and the specific recognition toward different targets, which renders supramolecular macrocycles an ideal type of building blocks for materials construction. Aggregation-induced emission (AIE) has been intensively investigated for two decades not only for the realization of solid-state fluorescent materials, but also for the fabrication...

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Controllable aggregation-induced emission based on a tetraphenylethylene-functionalized pillar[5]arene via host–guest recognition

Cited by 109 publications

References 28 publications

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

Self‐Assembly of Aggregation‐Induced‐Emission Molecules

Manipulating Aggregation‐Induced Emission with Supramolecular Macrocycles

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