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四苯基乙烯
RSC Advances · 2016 ·Vol. 6 ·期 87 ·84133-84138 · IF 3.289

High fluorescence intensity poly(aryl ether ketone)s containing tetraphenylethylene moieties: preparation, characterization and fluorescent properties

Feng Li,Jiashuang Luan,Shuling Zhang,Yuchao Luo,Yinlong Du,Cong Gao,Guibin Wang

A novel monomer containing tetraphenylethylene-(2,6-difluorophenyl)(4-(3-(4-1,2,2-triphenyl vinyl)phenoxy)propyl)phenyl)methanone (2F-TPE) was designed and synthesized by reaction of (4-(3-bromopropyl)phenyl)(2,6-difluorophenyl)methanone and 1-(4-hydroxyphenyl)-1,2,2-triphenylethene. A series of high fluorescence intensity poly(aryl ether ketone) copolymers containing tetraphenylethylene (TPE–PAEK) were prepared, which is the first report of preparing PAEK featuring tetraphenylethylene groups by polycondensation. The fluorescence and thermal properties of TPE–PAEK were characterized using fluorescence spectrophotometer, differential scanning calorimetry and thermogravimetric analysis respectively. The results indicated that tetraphenylethylene-based copolymers possessed high fluorescence intensity at a low concentration both in solids and in water/THF mixtures. TPE–PAEK still presented strong fluorescence intensity at elevated temperature up to 90 °C. In addition, TPE–PAEK possess excellent thermal stability.

CAS / MDL: 1478-61-1
研究领域: 材料科学 · 化学工程
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ORGANIC ELECTRONICS · 2022 · IF 3.868

Bright and efficient sky-blue perovskite light-emitting diodes via doping of π-conjugated molecule tetraphenylethylene

Fang Yuan,Feifei Fu,Chunrong Zhu,Xiaoyun Liu,Chenxing Liu,Jinfei Dai,Hua Dong,Bo Jiao,Fanghui Zhang,Zhaoxin Wu

As a star material, to date, hybrid perovskites with green and red emission show high photoluminescence quantum yields , and the external quantum efficiency (EQE) of perovskite light-emitting diodes (PeLEDs) has exceeded 20%. However, due to the poor film quality and large energy level mismatch, the performance of blue PeLEDs still lags far behind. Herein, a π-conjugated tetraphenylethylene (TPE) doping strategy is demonstrated to improve both the efficiency and stability of sky-blue PeLEDs. With proper TPE doping, the defects are passivated and the energy levels of multi-cation perovskite are elevated, resulting in a smooth and dense film with high PLQY (∼27.8%). The champion PeLED shows a brightness of 12,963 cd/cm 2 at 484 nm and maximum EQE of 6.97%. Moreover, after TPE doping, the operational stability of the PeLED increases from 290 s to 960 s under continuous working condition. The π-conjugated molecule doping strategy could open up a new avenue for the design of high-performing blue PeLEDs.

研究领域: 材料科学 · 光电技术
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

A metal-complex based chemosensor for the detection of riboflavin and folate

Haobo Xie,Mingu Zhou,Xiaorui Cui,Chao Li,Yongjun Wu,Xinjuan Luo,Mao-Sen Yuan

The vitamins of riboflavin and folate are necessary nutrients for maintaining the proper functioning of human body. Riboflavin and folate deficiency will cause nerve damage, leading to peripheral neuritis, depression, tongue inflammation and other diseases. The sensitive detection of riboflavin and folate keeps its significance for patients and food quality control. In this study, a quinoline-pyridine-combined chemosensor ( HQ-TPE ) modified by tetraphenylethene was developed. After chelating Cd 2+ , the chemosensor exhibited high selectivity and sensitivity for riboflavin and folate. Moreover, it can discriminate the two different vitamins through different fluorescent responses, which should arise from the different intermolecular π-π interactions between the sensor HQ-TPE and the analyte upon coordination of riboflavin or folate with Cd 2+ . More importantly, the chemosensor could be used in visual semi-quantitative determination of riboflavin and folate in real samples (milk and lettuce). Therefore, the sensor presented here will not only be a powerful tool for the detection of riboflavin and folate, but also provides a new template for the design of metal complex as fluorescent sensor.

研究领域: 生物化学 · 分析化学
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JOURNAL OF MOLECULAR STRUCTURE · 2021 · IF 3.196

Tetraphenylethylene-rufigallol-tetraphenylethylene trimers: Novel fluorescence liquid crystals in aggregated states

Xiaoyi Zhang,Guoliang Lin,Hongyu Guo,Fafu Yang

This work reported two novel liquid crystals with good fluorescence in aggregated states. Two tetraphenylethylene-rufigallol-tetraphenylethylene trimers (compounds 6a and 6b ) were prepared in simple procedure. The columnar liquid crystalline behaviors of 6a and 6b were confirmed by the analysis of differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction. Compound 6b exhibited an ordered hexagonal columnar mesophase. They possessed excellent AIE fluorescence properties in THF-H 2 O solution, solid film and mesophase. The fluorescence quantum yields of compounds 6a and 6b were 12% and 22% in solid films, 14% and 24% in mesophase, respectively. The experimental results showed that the liquid crystalline properties and fluorescence properties were tuned by the lengths of the terminal alkyl chains.

研究领域: 材料化学 · 液晶科学 · 光学材料
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ACS Nano · 2021 · IF 15.881

Tunable Circularly Polarized Luminescence from Single Crystal and Powder of the Simplest Tetraphenylethylene Helicate

Ming Hu,Feng-Ying Ye,Cong Du,Weizhou Wang,Ting-Ting Zhou,Miao-Li Gao,Minghua Liu,Yan-Song Zheng

Tetraphenylethylene and its derivatives are a class of aggregation-induced emission (AIE) compounds that are most extensively and successfully studied. It has been found that the simplest TPE is easy to crystallize into homochiral M crystals or P crystals. However, no research on circularly polarized luminescence (CPL) of TPE solid is documented. In this paper, we report that TPE can grow into big and nonefflorescent single crystals in single helical conformation and has large birefringence that is comparative with commercially available products. The TPE single crystals can emit strong CPL with a very high glum value up to 0.53. Moreover, the sense and magnitude of CPL signals can be willfully tuned by simple rotation of the single crystal due to anisotropy of the crystals. This simple and promising CPL photonic material integrates emission, chirality, and birefringence together in one single crystal without needing an additional chiral dopant or conjugate polymer that can produce linearly polarized light. After being ground into fine powder and pressed as KBr pellets, the obtained nanocrystals of TPE also emit strong CPL light. Exceptionally, by mixing other achiral luminescent dyes together with TPE powder in KBr pellets, induced CPL signals were obtained, which could give full-color CPL emission. Although there were no interactions between TPE and the dyes in the pellets, induced CPL signals were realized through radiative energy transfer, providing a very simple method for the tuning of CPL emission.

研究领域: 材料科学 · 光学
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Journal of Materials Chemistry C · 2014 ·Vol. 2 ·期 34 ·7001-7012 · IF 0

Tetraphenylethene-decorated carbazoles: synthesis, aggregation-induced emission, photo-oxidation and electroluminescence

Wen-Liang Gong,Bo Wang,Matthew. P. Aldred,Chong Li,Guo-Feng Zhang,Tao Chen,Lei Wang,Ming-Qiang Zhu

In this paper, the bromination of carbazole has been controlled and then subsequent mono, di, tri and tetra-bromocarbazoles have been subjected to Suzuki cross-coupling to yield a series of carbazole-tetraphenylethene (TPE) materials with varying numbers of peripheral TPE groups. Accompanied by 2,7-dibromo-carbazole, five new Cz-TPE materials are successfully synthesized. All the Cz-TPEs are non-fluorescent in THF and emit strong blue-green fluorescence in aggregate states (fw = 90%) and thin films because of their aggregation induced emission (AIE) nature. In THF (10−5 M) solution, all the Cz-TPEs emit deep blue fluorescence after UV irradiation and we find that the more the TPE groups, the slower the enhancement of fluorescence. In thin films (40 nm), the emission maximum blue shift decreases and finally becomes non-emissive after about 1.5 h of UV irradiation for all the Cz-TPEs. We suppose these optical properties are attributed to photo-induced irreversible changes of TPE to diphenylphenanthrene derivatives. The photo-oxidation process for Cz-1TPE has been investigated and proved by HPLC analysis, 1H NMR and LS-MS. Electrochemical properties of all the Cz-TPEs are investigated by cyclic voltammetry and with UV-absorption spectra, and their energy levels are calculated. Finally, we applied the Cz-TPEs to organic light emitting diode (OLED) devices by the spin coating deposition process with OLED devices configuration: ITO/PEDOT (40 nm)/Cz-TPEs (50 nm)/TPBi (40 nm)/LiF (1 nm)/Al (100 nm). All EL devices emit blue-green light with a maximum luminance (Lmax) of 2858, 1353, 986, 2088 and 1129 cd m−2, a maximum current efficiency (ηc,max) of 3.5, 4.9, 3.1, 3.1 and 5.5 cd A−1, a maximum power efficiency (ηP,max) of 2.1, 3.9, 2.2, 1.8 and 3.1 lm W−1 and a turn on voltage (Von) of 3.5, 3.5, 3.3, 3.6 and 4.2 V for Cz-1TPE, Cz-2TPE, Cz-3TPE, Cz-4TPE, Cz-2TPE (2,7), respectively.

研究领域: 有机化学 · 材料科学 · 光电材料
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DYES AND PIGMENTS · 2019 · IF 4.018

A porous tetraphenylethylene-based polymer for fast-response fluorescence sensing of Fe(III) ion and nitrobenzene

Yingting Zheng,Hailong Wang,Jianzhuang Jiang

A fluorescent porous tetraphenylethylene-based organic polymer ( PTOP ) was constructed by the reaction of 5,5',5'',5‴-(ethene-1,1,2,2-tetrayltetrakis(benzene-4,1-diyl))tetrakis(pyrimidin-2-amine) and cyanuric chloride in the presence of potassium carbonate. CO 2 sorption experiment at 195 K reveals the permanent porosity of PTOP with a Brunauer-Emmett-Teller surface area of 227 m 2  g −1 . In particular, the existence of rich secondary amines and pyrimidine nitrogen atoms surrounding the 1,3,5-triazine moieties in PTOP provides abundant chelating sites for metal ions, endowing a fast-response and sensitive fluorescence sensing Fe(III) with a low limit of detection of 4.5 μM. In addition, this polymer also shows an excellent sensing performance towards nitrobenzene with good selectivity and a low detection limit of 1.6 nM.

研究领域: 材料科学 · 分析化学
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2020 · IF 3.306

Synthesis of isoniazid-substituted tetraphenylethylene stereoisomers with dramatic differences on aggregate morphologies, optical and mechanocharomic properties

Zhixiang Lu,Shuhan Lu,Yi Cheng,Yu Qin,Shaoxiong Yang,Xiaolan Liu,Wenwen Fan,Liyan Zheng,Hongbin Zhang

Stereoisomers play an irreplaceable prominent role in life sciences. In molecular engineering, the isomers have been continuously designed and synthesized, and their interrelationships among structure-property-function have also been explored. However, the difficulties in purification and structural confirmation of tetraphenylethene (TPE) derivatives' stereoisomers hinder their structural diversity and scope of functions. Meanwhile, there were few researches on the macroscopic optical differences about TPE derivatives isomers. Herein, isoniazid-substituted TPE derivatives stereoisomers have been synthesized, as confirmed by single crystal data, mass spectrometry and NMR spectroscopy. The different photophysical properties were caused by the introduction of functional group isoniazid on the periphery of TPE. These isomers possessed dramatic differences in fluorescent properties, and exhibited diverse changes in response to stimuli. They also have distinct aggregated self-assembly morphologies because of different intermolecular hydrogen bonding, and they can be used as efficient fluorescent probes for detecting copper. Based on the coordination-driven sensing system, the morphologies of isomers aggregates changed significantly after interaction with copper, and the stoichiometry between them is 2:1. The theoretical calculation demonstrated that they have obvious intramolecular charge transfer behavior. Our research provided a good strategy for designing different substituted groups that can produce various functions and have more potential applications.

研究领域: 化学 · 材料科学 · 生物医学工程
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SENSORS AND ACTUATORS B-CHEMICAL · 2017 · IF 5.401

Glucose detection via glucose-induced disaggregation of ammonium-modified tetraphenylethylene from polyanion

Huihui Li,Ling Zhu,Xinyue Zhu,Haixia Zhang

A fluorescent glucose probe designed by a new strategy was reported. The probe consisted of ammonium-modified tetraphenylethylene (TPEA) with the feature of aggregation-induced emission and phenylboronic acid-containing polyanion that induced aggregation of TPEA via electrostatic interaction. With adding glucose and glucose oxidase, the produced H 2 O 2 converted phenylboronic acid into weaker acid phenol, which reduced negatively charges on the polyanion, resulting in the disaggregation of TPEA. This probe well qualified glucose in the range from 4 to 50   μM with detection limit of 2.6   μM. Moreover, it exhibited excellent selectivity and was successfully applied to blood glucose detection. As far as we know, no report has been published on glucose detection based on acidity difference between phenylboronic acid and phenol.

研究领域: 生物化学 · 分析化学
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MACROMOLECULAR RAPID COMMUNICATIONS · 2022 ·Vol. 43 ·期 18 ·2200154 · IF 5.006

Configuration-Dependent Liquid Crystal and Gel Behaviors of Tetraphenylethene-Containing Main-Chain Copolyesters

Jing Wang,Tian Wang,Qian Jiang,Yuping Zhang,Yuan Qiu,Hong Wang,Guochuan Yin,Yonggui Liao,Xiaolin Xie

The construction of aggregation-induced emission-active (AIE-active) gelators with liquid crystal properties remains a challenge. Moreover, the effects of AIE configuration on liquid crystal, gel and AIE behaviors in one system are unclear. Herein, two main-chain liquid crystalline copolyester gelators with a single configuration of AIEgen TPE, mesogen biphenyl, and pendent amide groups are synthesized through melt polycondensation. Both copolyesters display smectic phase, while E-P20 possesses a wider temperature range of liquid crystal and a narrower layer distance owing to the more serious nonlinear “defect” of Z-TPE than E-TPE units. In addition, E-P20 and Z-P20 can form AIE-active gels with the minimum gelation concentration (MGC) values of 10 and 4 wt% in ethyl acetate mainly via hydrogen bonds between the pendent amide groups, respectively. These AIE-active gels show potential applications in temperature sensor, information storage, and so on.

CAS / MDL: 110-71-4
研究领域: 材料科学 · 化学
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ACS Applied Materials & Interfaces · 2023 · IF 9.5

Asymmetric Synthesis of Tetraphenylethylene Helicates and Their Full-Color CPL Emission with High glum and High Fluorescence Quantum Yield

Feng-Ying Ye,Ming Hu,Yan-Song Zheng

Tetraphenylethylene (TPE) helicates with single helical handedness not only owe high fluorescence quantum yield but also possess good helical chirality, showing an excellent circularly polarized luminescence active material. In this work, a new method for directly obtaining single-handed TPE helicates has been developed. By using chiral p-phenylenediamine derivatives as an intramolecular cyclization reagent of TPE, the single-handed propeller-like conformation and stable helical chirality of the TPE unit were obtained, avoiding complicated and expensive HPLC chiral column separation. The as-prepared chiral TPE helicates displayed strong emission with an almost quantitative fluorescence quantum yield (Φf) and strong circularly polarized luminescence (CPL). In addition, the chirality and CPL signals of the TPE helicates could be significantly magnified by the helical arrangement together with 4′-pentyl-4-biphenylcarbonitrile (5CB) liquid crystal molecules. Moreover, full-color CPL emissions with both a high absolute CPL dissymmetrical factor up to 0.43 and high Φf were afforded.

研究领域: 有机化学 · 材料科学 · 光学
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ANALYTICA CHIMICA ACTA · 2021 · IF 6.558

Heteroatom-free conjugated tetraphenylethylene polymers for selectively fluorescent detection of tetracycline

Qiu Zhuang,Cheng Zhang,Haiyan Zhuang,Hanyu Deng,Xiangpeng Lin,Yan Li,Hao Chen,Aming Xie,Wei Dong

The antibiotic tetracycline (Tc) is a major contaminant in food and water, with adverse effects on both ecosystems and human health. The development of novel sensors for tetracycline detection is of great importance. In this work, we develop a novel heteroatom-free conjugated tetraphenylethylene polymer (TPE-CMP) fluorescence sensor for the detection of tetracycline. In the presence of Tc, the emission fluorescence of TPE-CMP was quenched by the photoinduced electron transfer mechanism to achieve high sensitivity. The polymers can detect tetracycline at a concentration of 0–100 μg/mL with a good linear correlation (0.99), and the limit of detection (LOD) is 1.23 μg/mL. Furthermore, TPE-CMP has excellent selectivity in detecting Tc in the presence of various anti-interference analytes, including ions and antibiotics. In addition, the practical feasibilities of TPE-CMP for Tc sensing were further investigated in milk, urine and wastewater samples with satisfactory recoveries (from 94.96% to 112.53% for milk, from 96.41% to 99.31% for urine and from 98.54% to 100.52% for wastewater). We have designed and synthesized TPE-CMP based on heteroatom-free for the specific fluorescence detection of tetracycline, expanding the range of fluorescence detection sensors and offering great promise for practical applications.

研究领域: 分析化学 · 环境科学 · 食品科学
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