4.6 Article

Tetraphenylethene-triphenylene oligomers with an aggregation-induced emission effect and discotic columnar mesophase

期刊

RSC ADVANCES
卷 3, 期 33, 页码 14099-14105

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ra41874j

关键词

-

资金

  1. National Natural Science Foundation of China [51273133, 51073112, 50973076]
  2. Youth Foundation of Sichuan Educational Committee [11ZB075]

向作者/读者索取更多资源

Tetraphenylethene derivatives not only exhibit aggregation-induced emission (AIE) effects, but also can form a mesophase with a turbine-like rigid core. Here we report the synthesis of three tetraphenylethene-triphenylene oligomers 7, 8E and 8Z by a CuSO4/sodium ascorbate catalyzed alkyne-azide cycloaddition reaction (CuAAC), and the successful separation of the cis-and trans-isomers by column chromatography. The structure and conformation of the oligomers were fully characterized. The photophysical properties were studied by using UV-vision and photoluminescent (PL) spectroscopy. The morphology of the aggregates was investigated by scanning electron microscopy (SEM), and the thermal stability and mesomorphic properties were investigated using thermal gravimetric analysis (TGA), polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD). The results revealed that the oligomers possess an AIE effect, but display no mesomorphism. However, 7 exhibits a hexagonal columnar mesophase when mixed with 2,4,7-trinitrofluorenone (TNF), forming a charge transfer complex.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.6
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Nanoscience & Nanotechnology

Supramolecular Room-Temperature Phosphorescent Hydrogel Based on Hexamethyl Cucurbit[5]uril for Cell Imaging

Xi-Ran Sun, Hai-Ping Yang, Wei Zhang, Shuai Zhang, Jian-Hang Hu, Ming Liu, Xi Zeng, Qiu Li, Carl Redshaw, Zhu Tao, Xin Xiao

Summary: The hosts-guest interaction in the HmeQ[5]/DB system was studied, and a new supramolecular gel was prepared through a simple heating/mixing cooling method. The gel showed temperature sensitivity and exhibited double emission ability at room temperature due to its ordered microstructure, which prevented nonradiative transition of the embedded fluorescence material BrNp. Moreover, the gel showed good biocompatibility and low biotoxicity, making it suitable for cytoplasmic staining of HeLa cells.

ACS APPLIED MATERIALS & INTERFACES (2023)

Article Engineering, Environmental

New dual-mode orthogonal tunable fluorescence systems based on cucurbit [8]uril: White light, 3D printing, and anti-counterfeit applications

Ting Ting Zhang, Xi Nan Yang, Jian Hang Hu, Yang Luo, Hou Jing Liu, Zhu Tao, Xin Xiao, Carl Redshaw

Summary: In this work, a supramolecular approach was used to control emission and generate white light for applications in 3D printing and counterfeiting. Two dual-mode fluorescence systems were developed, which could provide bright white emission and be easily controlled by temperature. The systems showed promising potential in LED lamps, polymeric matrices, and practical applications such as anti-counterfeiting materials.

CHEMICAL ENGINEERING JOURNAL (2023)

Review Chemistry, Multidisciplinary

Stimuli-responsive mechanically interlocked molecules constructed from cucurbit[n]uril homologues and derivatives

Jing-Xin Liu, Kai Chen, Carl Redshaw

Summary: Since the successful separation of different cucurbit[n]uril homologues in 2001, the field of cucurbit[n]uril supramolecular chemistry has rapidly developed. The combination of Q[n] cavity size and various external stimuli has led to the creation of various Q[n]-based mechanically interlocked molecules (MIMs), including (pseudo)rotaxanes, catenanes, dendrimers, and poly(pseudo)rotaxanes. This review article highlights the important advancements in the field of Q[n]-based MIMs over the past two decades, discusses examples of heterowheel (pseudo)rotaxanes and poly(pseudo)rotaxanes involving Q[n]s, and reflects on the opportunities and challenges of constructing Q[n]-based stimuli-responsive MIMs.

CHEMICAL SOCIETY REVIEWS (2023)

Article Chemistry, Multidisciplinary

4,4'-Biphenyldisulfonic acid induced coordination polymers of symmetrical tetramethyl cucurbit[6] uril with alkaline-earth metals for detection of antibiotics

Kai Chen, Zhao-Qiang Zhu, Ming-Hui Zhang, Xiang Yang, Jie Li, Chen Chen, Carl Redshaw

Summary: Based on the analysis of the crystal structures of three coordination polymers, it was found that the deprotonated 4,4'-biphenyldisulfonic acid plays an important role in the self-assembly of these coordination polymers. In complexes 1 and 2, only the TMeQ[6] is involved in coordination with the Ca2+ and Sr2+ ions. The BPDS2- is involved in outer-surface interactions with the TMeQ[6]. Meanwhile, in complex 3, the BPDS2- is also coordinated with the Ba2+ ion. These coordination polymers provide a new strategy to design and construct Q[n]-based poly-dimensional coordination polymers, which can be built by one-dimensional Q[n]-metal coordination chains via outer-surface interactions. Furthermore, complex 1 can detect NFX (norfloxacin) molecules with high selectivity.

CRYSTENGCOMM (2023)

Article Chemistry, Multidisciplinary

Sulfonate ligand-induced formation of alkali metal-cucurbit[5]uril-based assemblies

Jing Xu, Qi Wang, Wei-Wei Ge, Dong Wu, Carl Redshaw, Kai Chen

Summary: In this study, 1,5-naphthalene disulfonic acid (H2NDS) was used as a structure-directing agent to construct cucurbit[5]uril-based supramolecular assemblies. Four novel assemblies were obtained by adding alkali metal cations to the Q[5]-H2NDS system. These assemblies exhibited similar structures and the main difference was the coordination modes of the metal cations. Compound 2 showed high selectivity in detecting NFX molecules and could capture AR, CV, and MB from aqueous media.

CRYSTENGCOMM (2023)

Article Chemistry, Multidisciplinary

Room-temperature triphenylene-based discotic liquid crystal dimers: effects of amide linkage and central fluoromethylene spacer

Wen-Hao Yu, Yan-Hong Wang, Chun Feng, Hai-Liang Ni, Ping Hu, Bi-Qin Wang, Ke-Qing Zhao, Qiang Fu

Summary: Two series of triphenylene-based dimers with different fluoromethylene spacer lengths were synthesized and their phase behavior was investigated. The length of the spacer had a minor effect on the phase transition temperatures of the dimers. However, the dimers with a longer fluoromethylene spacer exhibited higher clearing points and wider mesomorphic phase ranges compared to their hydrocarbon analogs. Additionally, amide-linked dimers showed good gelation properties, indicating the collaboration of hydrogen bonding and pi interactions in gel formation.

LIQUID CRYSTALS (2023)

Article Chemistry, Organic

Chromium-Catalyzed Defluorinative Reductive Coupling of Aldehydes with gem-Difluoroalkenes

Yu-Tao Liu, Yu-Hang Fan, Yan Mei, Dong-Jie Li, Yan Jiang, Wen-Hao Yu, Fei Pan

Summary: A mild and convenient defluorinative reductive cross coupling between gem-difluoroalkenes and aliphatic aldehydes has been developed, yielding diverse silyl-protected beta-fluorinated allylic alcohols. The reaction is simple to carry out and exhibits good functional group tolerance, providing moderate to excellent yields. The utility of this method is demonstrated by converting the products into various bioactive fluorinated compounds, indicating its potential applications in drug discovery and biochemistry.

ORGANIC LETTERS (2023)

Article Chemistry, Physical

A study of the supramolecular assembly formed by cucurbit[7]uril and 4-cyanophenol

Zhi-Chao Yu, Yun Lu, Jie Zhao, Jing -Jing Dai, Guo-Rong Chen, Pei-Hui Shan, Carl Redshaw, Zhu Tao, Xin Xiao

Summary: The binding interaction between 4-cyanophenol (4-CY) and cucurbit[7]uril has been studied. The absorption and emission spectra obtained in aqueous solution revealed the formation of a 1:1 host-guest type complex. By introducing [ZnCl4]2- and Ca2+ as structural inducers, a single crystal structure was obtained, showing weak interactions between 4-CY and Q[7] or [ZnCl4]2-. The supramolecular framework based on Q[7] exhibited a Chinese knot-like structure.

JOURNAL OF MOLECULAR STRUCTURE (2023)

Article Nanoscience & Nanotechnology

Novel pyrene-based aggregation-induced emission luminogen (AIEgen) composite phase change fibers with satisfactory fluorescence anti-counterfeiting, temperature sensing, and high-temperature warning functions for solar-thermal energy storage

Jintao Huang, Yiwei Liu, Jiahui Lin, Jingtao Su, Carl Redshaw, Xing Feng, Yonggang Min

Summary: Novel phase change material (PCM) composite fiber films have been produced with temperature-dependent fluorescence change and stability, which can be used for applications in solar energy conversion and storage, high-temperature warning, and anti-counterfeiting.

ADVANCED COMPOSITES AND HYBRID MATERIALS (2023)

Article Chemistry, Multidisciplinary

Induction and Stabilization of Columnar Mesophases in Fluorinated Polycyclic Aromatic Hydrocarbons by Arene-Perfluoroarene Interactions

Ming-Mei Zhou, Jiao He, Hui-Min Pan, Qing Zeng, Hang Lin, Ke-Qing Zhao, Ping Hu, Bi-Qin Wang, Bertrand Donnio

Summary: This study describes a efficient transition-metal-free arene-fluorine nucleophilic substitution reaction for the straightforward synthesis of several Fluorinated Polycyclic Aromatic Hydrocarbons, and reports the investigation of their liquid crystalline and optical properties.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

Article Chemistry, Physical

K-region tetrasubstitute d deep-blue pyrene-base d luminogens: Visual detection of trace nitroaniline

Jing-Yi Cao, Ze-Dong Yu, Guang Yang, Xue-Can Wang, Lu Jiang, Xi Wang, Wen-Xuan Zhao, Shu-Hai Chen, Carl Redshaw, Chuan-Zeng Wang, Takehiko Yamato

Summary: In recent years, fluorescence sensors have been widely used in explosive detection due to their portability and high efficiency. In this study, two K-region tetrasubstituted deep-blue pyrene-based luminogens were designed and synthesized, and their optical properties were investigated by experimental and density functional theory (DFT) methods. The research results establish a low-cost and simple strategy for the detection of trace nitroaniline.

JOURNAL OF MOLECULAR STRUCTURE (2023)

Article Chemistry, Organic

Pyrene-Based Cationic Fluorophores with High Affinity for BF4 (-), PF6 (-), and ClO4 (-) Anions: Detection and Removal

Xu Zhou, Xiaohui Wang, Tian-Yu Zhang, Lingyi Shen, Xian-Jiong Yang, Qi-Long Zhang, Hong Xu, Carl Redshaw, Xing Feng

Summary: Anions are important for the balance and regulation of the environment and human health, but excess anions can cause ecological and environmental problems. This study synthesized water-soluble pyrene-based cationic fluorophores that exhibit high sensitivity for detecting and removing the anions BF4-, PF6-, and ClO4- in aqueous solutions. These fluorescent probes show turn-on emission characteristics even at low concentrations of anions, and also act as efficient precipitating agents. This work opens up new possibilities for using pyrene-based fluorophores as turn-on fluorescence probes for anion detection and as effective precipitating agents in environmental settings.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

A substituent-dependent deep-blue pyrene-based chemosensor for trace nitroaniline sensing

Hua-Long Li, Jing-Yi Cao, Ze-Dong Yu, Guang Yang, Zeng-Min Xue, Chuan-Zeng Wang, Wen-Xuan Zhao, Yi Zhao, Carl Redshaw, Takehiko Yamato

Summary: In this study, two pyrene-based luminogens with reasonable photoluminescence efficiency and blue emission were synthesized and characterized. They showed a sensitive response towards electron deficient nitroaromatics, especially nitroaniline, based on a photo-induced electron transfer mechanism. The detection limit for p-nitroaniline was as low as 8.58 x 10(-9) M, with a fluorescence quenching efficiency of up to 99.5%. These results provided a low-cost and simple strategy for trace nitroaniline sensing.

MATERIALS CHEMISTRY FRONTIERS (2023)

Article Chemistry, Physical

Ultralong nitrogen/sulfur Co-doped carbon nano-hollow-sphere chains with encapsulated cobalt nanoparticles for highly efficient oxygen electrocatalysis

Wei Zhang, Xingmei Guo, Cong Li, Jiang-Yan Xue, Wan-Ying Xu, Zheng Niu, Hongwei Gu, Carl Redshaw, Jian-Ping Lang

Summary: An efficient bifunctional electrocatalyst, Co-CNHSCs, consisting of ultralong N, S-doped carbon nano-hollow-sphere chains and encapsulated Co nanoparticles, is developed with superior catalytic activities for ORR and OER in alkaline media. The optimized catalyst Co-CNHSC-3 exhibits outstanding electrocatalytic abilities, including a high specific capacity of 1023.6 mAh g(Zn)(-1) and excellent reversibility after 80 hours at 10 mA cm(-2) in a Zn-air battery system.

CARBON ENERGY (2023)

Article Polymer Science

Fast thermally-responsive azatriphenylene ionic discotic liquid crystalline polymers with shape-memory properties

Xiao-Ping Xiong, Qian Yang, Ruo-Jun Wang, Ling-Yi Zeng, Wen-Hao Yu, Hong-Mei Chen, Hai-Liang Ni, Chun Feng, Ke-Qing Zhao, Ping Hu

Summary: Ionic discotic liquid crystalline polymers are versatile multifunctional polymers that exhibit electron and ion transport, luminescence, and thermal and mechanical responsiveness. In this study, IDLCPs with varying content ratios of cyclooctene and ionic monomer were successfully synthesized. The polymers displayed a hexagonal columnar mesophase and emitted yellow light photoluminescence. One of the copolymers exhibited excellent shape memory properties and ionic conductivity.

POLYMER CHEMISTRY (2023)

暂无数据