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Molecules
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Aggregation-Induced Emission: From Fundamental to Application
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Aggregation-Induced Emission: From Fundamental to Application

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Photochemistry".

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 14956

Special Issue Editors

Prof. Dr. Wenbo Wu

E-Mail Website
Guest Editor
Institute of Molecular Aggregation Science, Tianjin University, Tianjin 300072, China
Interests: aggregation-induced emission; conjugated polymer; dendritic macromolecules; biomedical materials; photo therapy; nonlinear optical materials
Prof. Dr. Zheng Zhao

E-Mail Website
Guest Editor
School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen, China
Interests: luminescence mechanism; AIE photosensitizer; NIR luminescent/photothermal materials; BioAIEgen/Natural AIE materials
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Haoke Zhang

E-Mail Website
Guest Editor
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
Interests: clusteroluminescence; through-space interaction; aggregation-induced emission
Prof. Dr. Fang Hu

E-Mail Website
Guest Editor
School of Biomedical Engineering, Southern Medical University, Guangzhou 510515, China
Interests: aggregation-induced emission; antibacterial photodynamic therapy; point-of-care testing; targeted fluorescence imaging; anthracene

Special Issue Information

Dear Colleagues,

The concept of aggregation-induced emission, which was firstly coined by Tang et al. in 2001, describes the photophysical phenomenon where some special non-luminescent molecules in solutions are induced to show bright emissions upon aggregate formation. As compared to traditional fluorophores, the greatest features or advantages of AIE fluorophores (usually termed as AIEgens) is the possible bright emission or highly efficient radiative transition in the aggregate state which is the most used condition for practical applications. The 20-year development has set a solid foundation for the fundamental study of the AIE field, and the concept has also been expanded from traditional enhanced fluorescence to other properties and functions, such as room temperature phosphorescence, circularly polarized luminescence, mechanoluminescence, aggregation-induced delayed fluorescence, clusterization-triggered emission, aggregation-induced generation of reactive oxygen species, photothermal, photoacoustic, etc., which brought AIEgens another step forward towards practical applications.

Based on this background, the goal of this Special Issue “Aggregation-Induced Emission: from Fundamental to Application” is to show the recent development of AIE fields, including the mechanism study, molecule design, as well as of diverse applications. We welcome original research, review, and perspective articles on themes including, but not limited to:

  • Establishment of new theories or mechanisms for AIEgens.
  • Design, synthesis and characterization of new molecules with AIE properties.
  • New properties and applications of AIE molecules.

Prof. Dr. Wenbo Wu
Prof. Dr. Zheng Zhao
Prof. Dr. Haoke Zhang
Prof. Dr. Fang Hu
Guest Editors

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Keywords

  • aggregation-induced emission
  • organic/polymeric functional materials
  • luminescence
  • molecular science
  • aggregation science

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Published Papers (6 papers)

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Research

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19 pages, 6005 KiB  
Article
Modulating the Luminescence, Photosensitizing Properties, and Mitochondria-Targeting Ability of D-π-A-Structured Dihydrodibenzo[a,c]phenazines
by Zhaozhi Zhang, Qijing Wang, Xinyi Zhang, Dong Mei and Ju Mei
Molecules 2023, 28(17), 6392; https://doi.org/10.3390/molecules28176392 - 1 Sep 2023
Cited by 1 | Viewed by 1377
Abstract
Herein, pyridinium and 4-vinylpyridinium groups are introduced into the VIE-active N,N′-disubstituted-dihydrodibenzo[a,c]phenazines (DPAC) framework to afford a series of D-π-A-structured dihydrodibenzo[a,c]phenazines in consideration of the aggregation-benefited performance of the DPAC module and the [...] Read more.
Herein, pyridinium and 4-vinylpyridinium groups are introduced into the VIE-active N,N′-disubstituted-dihydrodibenzo[a,c]phenazines (DPAC) framework to afford a series of D-π-A-structured dihydrodibenzo[a,c]phenazines in consideration of the aggregation-benefited performance of the DPAC module and the potential mitochondria-targeting capability of the resultant pyridinium-decorated DPACs (DPAC-PyPF6 and DPAC-D-PyPF6). To modulate the properties and elucidate the structure–property relationship, the corresponding pyridinyl/4-vinylpyridinyl-substituted DPACs, i.e., DPAC-Py and DPAC-D-Py, are designed and studied as controls. It is found that the strong intramolecular charge transfer (ICT) effect enables the effective separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of DPAC-PyPF6 and DPAC-D-PyPF6, which is conducive to the generation of ROS. By adjusting the electron-accepting group and the π-bridge, the excitation, absorption, luminescence, photosensitizing properties as well as the mitochondria-targeting ability can be finely tuned. Both DPAC-PyPF6 and DPAC-D-PyPF6 display large Stokes shifts (70–222 nm), solvent-dependent absorptions and emissions, aggregation-induced emission (AIE), red fluorescence in the aggregated state (λem = 600–650 nm), aggregation-promoted photosensitizing ability with the relative singlet-oxygen quantum yields higher than 1.10, and a mitochondria-targeting ability with the Pearson coefficients larger than 0.85. DPAC-D-PyPF6 shows absorption maximum at a longer wavelength, slightly redder fluorescence and better photosensitivity as compared to DPAC-PyPF6, which consequently leads to the higher photocytotoxicity under the irradiation of white light as a result of the larger π-conjugation. Full article
(This article belongs to the Special Issue Aggregation-Induced Emission: From Fundamental to Application)
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11 pages, 3102 KiB  
Article
Dextran-Cholesterol Carrier Encapsulated Efficient Photosensitizer for the Photodynamic Killing of Cancer Cells
by Biru Wu, Zhuoheng Gan, Shengchang Tao, Qiang Wang, Yuchen Song, Hua Zhong and Fang Hu
Molecules 2023, 28(11), 4404; https://doi.org/10.3390/molecules28114404 - 28 May 2023
Viewed by 2127
Abstract
Selective photodynamic therapy (PDT) for cancer cells is more efficient and much safer. Most selective PDTs are realized by antigene-biomarker or peptide-biomarker interactions. Here, we modified dextran with hydrophobic cholesterol as a photosensitizer carrier to selectively target cancer cells, including colon cancer cells, [...] Read more.
Selective photodynamic therapy (PDT) for cancer cells is more efficient and much safer. Most selective PDTs are realized by antigene-biomarker or peptide-biomarker interactions. Here, we modified dextran with hydrophobic cholesterol as a photosensitizer carrier to selectively target cancer cells, including colon cancer cells, and fulfilled selective PDT. The photosensitizer was designed with regular Aggregation-Induced Emission (AIE) units, including triphenylamine and 2-(3-cyano-4,5,5-trimethylfuran-2-ylidene)propanedinitrile. The AIE units can help to decrease the quenching effect in the aggregate state. The efficiency of the photosensitizer is further improved via the heavy atom effect after bromination modification. We found that the obtained photosensitizer nanoparticles could selectively target and ablate cancer cells after encapsulation into the dextran-cholesterol carrier. This study indicates that the polysaccharide-based carrier may have potential for cancer-targeting therapy beyond expectations. Full article
(This article belongs to the Special Issue Aggregation-Induced Emission: From Fundamental to Application)
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16 pages, 4264 KiB  
Article
Mitochondria-Targeted Fluorescent Nanoparticles with Large Stokes Shift for Long-Term BioImaging
by Xiao Li, Tao Zhang, Xuebo Diao, Li Yu, Yue Su, Jiapei Yang, Zibo Shang, Shuai Liu, Jia Zhou, Guolin Li and Huirong Chi
Molecules 2023, 28(9), 3962; https://doi.org/10.3390/molecules28093962 - 8 May 2023
Cited by 5 | Viewed by 2171
Abstract
Mitochondria (MITO) play a significant role in various physiological processes and are a key organelle associated with different human diseases including cancer, diabetes mellitus, atherosclerosis, Alzheimer’s disease, etc. Thus, detecting the activity of MITO in real time is becoming more and more important. [...] Read more.
Mitochondria (MITO) play a significant role in various physiological processes and are a key organelle associated with different human diseases including cancer, diabetes mellitus, atherosclerosis, Alzheimer’s disease, etc. Thus, detecting the activity of MITO in real time is becoming more and more important. Herein, a novel class of amphiphilic aggregation-induced emission (AIE) active probe fluorescence (AC-QC nanoparticles) based on a quinoxalinone scaffold was developed for imaging MITO. AC-QC nanoparticles possess an excellent ability to monitor MITO in real-time. This probe demonstrated the following advantages: (1) lower cytotoxicity; (2) superior photostability; and (3) good performance in long-term imaging in vitro. Each result of these indicates that self-assembled AC-QC nanoparticles can be used as effective and promising MITO-targeted fluorescent probes. Full article
(This article belongs to the Special Issue Aggregation-Induced Emission: From Fundamental to Application)
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14 pages, 4798 KiB  
Article
Quinoline-Malononitrile-Based Aggregation-Induced Emission Probe for Monoamine Oxidase Detection in Living Cells
by Chuthamat Duangkamol, Sirilak Wangngae, Sirawit Wet-osot, Onnicha Khaikate, Kantapat Chansaenpak, Rung-Yi Lai and Anyanee Kamkaew
Molecules 2023, 28(6), 2655; https://doi.org/10.3390/molecules28062655 - 15 Mar 2023
Cited by 3 | Viewed by 2136
Abstract
A quinoline-malononitrile (QM)-based aggregation-induced emission probe was developed to detect MAOs in cells through an enzymatic reaction followed by β-elimination. After being incubated at 37 °C, QM-NH2 responded to the MAO enzymes with great specificity and within just 5 min. This 5 [...] Read more.
A quinoline-malononitrile (QM)-based aggregation-induced emission probe was developed to detect MAOs in cells through an enzymatic reaction followed by β-elimination. After being incubated at 37 °C, QM-NH2 responded to the MAO enzymes with great specificity and within just 5 min. This 5 min responsive mechanism was fast, with the limit of detection (LOD) at 5.49 and 4.76 µg mL−1 for MAO-A and MAO-B, respectively. Moreover, QM-NH2 displayed high enzyme specificity even in the presence of high concentrations of biological interferences, such as oxidizing and reducing agents, biothiols, amino acids, and glucose. Furthermore, QM-NH2 demonstrated biocompatibility as the cells retained more than 70% viability when exposed to QM-NH2 at concentrations of up to 20 µM. As a result, QM-NH2 was used to detect MAO-A and MAO-B in SH-SY5Y and HepG2 cells, respectively. After 1h incubation with QM-NH2, the cells exhibited enhanced fluorescence by about 20-fold. Moreover, the signal from cells was reduced when MAO inhibitors were applied prior to incubating with QM-NH2. Therefore, our research recommends using a QM probe as a generic method for producing recognition moieties for fluorogenic enzyme probes. Full article
(This article belongs to the Special Issue Aggregation-Induced Emission: From Fundamental to Application)
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14 pages, 3174 KiB  
Article
Aggregation-Induced Intermolecular Charge Transfer Emission for Solution-Processable Bipolar Host Material via Adjusting the Length of Alkyl Chain
by Wei Jiang, Guimin Zhao, Wenwen Tian and Yueming Sun
Molecules 2022, 27(22), 8099; https://doi.org/10.3390/molecules27228099 - 21 Nov 2022
Cited by 2 | Viewed by 2430
Abstract
Molecules with donor–spacer–acceptor configuration have been developed rapidly given their peculiar properties. How to utilize intermolecular interactions and charge transfers for solution-processed organic light-emitting diodes (OLEDs) greatly relies on molecular design strategy. Herein, soluble luminophores with D-spacer-A motif were constructed via shortening the [...] Read more.
Molecules with donor–spacer–acceptor configuration have been developed rapidly given their peculiar properties. How to utilize intermolecular interactions and charge transfers for solution-processed organic light-emitting diodes (OLEDs) greatly relies on molecular design strategy. Herein, soluble luminophores with D-spacer-A motif were constructed via shortening the alkyl chain from nonane to propane, where the alkyl chain was utilized as a spatial linker between the donor and acceptor. The alkyl chain blocks the molecular conjugation and induces the existence of aggregation-induced intermolecular CT emission, as well as the improved solubility and morphology in a solid-state film. In addition, the length of the alkyl chain affects the glass transition temperature, carrier transport and balance properties. The mCP-3C-TRZ with nonane as the spacer shows better thermal stability and bipolar carrier transport ability, so the corresponding solution-processable phosphorescent organic light-emitting diodes exhibit superior external quantum efficiency of 9.8% when using mCP-3C-TRZ as a host material. This work offers a promising strategy to establish a bipolar host via utilizing intermolecular charge transfer process in an aggregated state. Full article
(This article belongs to the Special Issue Aggregation-Induced Emission: From Fundamental to Application)
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Review

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23 pages, 4975 KiB  
Review
Recent Progress in Type I Aggregation-Induced Emission Photosensitizers for Photodynamic Therapy
by Yuewen Yu, Hanyu Jia, Yubo Liu, Le Zhang, Guangxue Feng and Ben Zhong Tang
Molecules 2023, 28(1), 332; https://doi.org/10.3390/molecules28010332 - 31 Dec 2022
Cited by 23 | Viewed by 3836
Abstract
In modern medicine, precision diagnosis and treatment using optical materials, such as fluorescence/photoacoustic imaging-guided photodynamic therapy (PDT), are becoming increasingly popular. Photosensitizers (PSs) are the most important component of PDT. Different from conventional PSs with planar molecular structures, which are susceptible to quenching [...] Read more.
In modern medicine, precision diagnosis and treatment using optical materials, such as fluorescence/photoacoustic imaging-guided photodynamic therapy (PDT), are becoming increasingly popular. Photosensitizers (PSs) are the most important component of PDT. Different from conventional PSs with planar molecular structures, which are susceptible to quenching effects caused by aggregation, the distinct advantages of AIE fluorogens open up new avenues for the development of image-guided PDT with improved treatment accuracy and efficacy in practical applications. It is critical that as much of the energy absorbed by optical materials is dissipated into the pathways required to maximize biomedical applications as possible. Intersystem crossing (ISC) represents a key step during the energy conversion process that determines many fundamental optical properties, such as increasing the efficiency of reactive oxygen species (ROS) production from PSs, thus enhancing PDT efficacy. Although some review articles have summarized the accomplishments of various optical materials in imaging and therapeutics, few of them have focused on how to improve the phototherapeutic applications, especially PDT, by adjusting the ISC process of organic optics materials. In this review, we emphasize the latest advances in the reasonable design of AIE-active PSs with type I photochemical mechanism for anticancer or antibacterial applications based on ISC modulation, as well as discuss the future prospects and challenges of them. In order to maximize the anticancer or antibacterial effects of type I AIE PSs, it is the aim of this review to offer advice for their design with the best energy conversion. Full article
(This article belongs to the Special Issue Aggregation-Induced Emission: From Fundamental to Application)
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