197153-87-0Relevant articles and documents
Construction of self-assembled nanostructure-based tetraphenylethylene dipeptides: Supramolecular nanobelts as biomimetic hydrogels for cell adhesion and proliferation
Lin, Hsin-Chieh,Mohammed, Mohiuddin,Talloj, Satish Kumar
, p. 7483 - 7493 (2020)
Supramolecular fluorescent materials with aggregation-induced emission (AIE) characteristics have promising applications as fluorescent probes for bio and chemosensors. In this study, a versatile low molecular weight tetraphenylethylene dipeptide hydrogelator (TPE-YY) with efficient AIE characteristics was developed, which was able to form hydrogels in a broad pH range from 3.7 to 10.2. The self-assembly of this hydrogel is completely pH-dependent, with significant structural transitions from high to low pH. At a relatively high pH value (10.2), a weak transparent hydrogel with an entangled network of nanofibers was obtained, while upon neutralization (pH 7.2) with dilute HCl, a stable semi-transparent gel with twisted nanobelts was formed. When the pH of the hydrogel was reduced to below 5.7, a turbid viscous gel and precipitation appeared with the thickening of the nanobelts. Surprisingly, the hydrogel resulting from the glucono-δ-lactone triggered gel showed only nanofibers independent of pH. The nature of the hydrogels and the nanostructures at different pH values were thoroughly examined and discussed via oscillatory rheology, electron microscopy and various spectroscopic techniques {1HNMR, 2D-NMR, Fourier transform infrared (FTIR) and Circular dichroism (CD)}. Interestingly, the self-assembled hydrogel exhibited excellent biocompatibility over 95% using hydrogel leachables on two different cell lines, 3A6 (human MSCs) and L929 (mouse fibroblast cells). Moreover, the self-assembled nanobelts formed at neutral pH showed excellent cell adhesion and proliferation of 3A6 cells, whereas the nanofibers showed poor cell adhesion and proliferation. Overall, we demonstrate the importance of chemical design for the formation of self-assembled nanobelts and supramolecular hydrogels at physiological pH with selective cell adhesion and proliferation, presenting a promising applications in tissue engineering and regenerative medicine. This journal is
Dual aggregation-induced emission for enhanced fluorescence sensing of furin activity in vitro and in living cells
Liu, Xiaomei,Liang, Gaolin
, p. 1037 - 1040 (2017)
The aggregation-induced emission (AIE) effect has recently been widely applied for biomarker sensing. But developing “smart” strategies to effectively aggregate the AIE fluorogen and additionally enhance the fluorescence emission remain challenging. In th
Specific detection of cancer cells through aggregation-induced emission of a light-up bioprobe
Chen, Jian,Jiang, Hong,Zhou, Huipeng,Hu, Zhenzhen,Niu, Niu,Shahzad, Sohail Anjum,Yu, Cong
, p. 2398 - 2401 (2017)
A cancer cell specific aptamer was labeled with an aggregation-induced emission (AIE) probe for the first time. Using it as a light-up bioprobe, a specific cancer cell detection method is developed.
A thermally stable and reversible microporous hydrogen-bonded organic framework: aggregation induced emission and metal ion-sensing properties
Zhou, Hui,Ye, Qun,Wu, Xiangyang,Song, Jing,Cho, Ching Mui,Zong, Yun,Tang, Ben Zhong,Hor, T.S. Andy,Yeow, Edwin Kok Lee,Xu, Jianwei
, p. 11874 - 11880 (2015)
A microporous hydrogen-bonded organic framework (HOF) derived from a polyhedral oligomeric silsesquioxane (POSS) intermediate and an aggregation-induced emission (AIE) luminogen tetraphenylethene (TPE) derivative has been synthesized and structurally char
Molecular luminogens based on restriction of intramolecular motions through host-guest inclusion for cell imaging
Liang, Guodong,Lam, Jacky W. Y.,Qin, Wei,Li, Jie,Xie, Ni,Tang, Ben Zhong
, p. 1725 - 1727 (2014)
We developed a new strategy to restrict the motions of AIE molecules through host-guest inclusion, affording a catalogue of new molecular luminogens.
A unimolecular theranostic system with H2O2-specific response and AIE-activity for doxorubicin releasing and real-time tracking in living cells
Gao, Xiaoying,Cao, Jie,Song, Yinuo,Shu, Xiao,Liu, Jianzhao,Sun, Jing Zhi,Liu, Bin,Tang, Ben Zhong
, p. 10975 - 10979 (2018)
A theranostic drug delivery system composed of tetraphenyl-ethene (AIEgen), benzyl boronic ester (trigger), and doxorubicin (drug) was designed and synthesized; its utilities for cell imaging, drug delivery tracking, and cancer cell cytociding were evalua
Homogeneous probing of lipase and α-amylase simultaneously by AIEgens
Shi, Jie,Deng, Qianchun,Li, Ya,Zheng, Zhe,Shangguan, Huijuan,Li, Lu,Huang, Fenghong,Tang, Bo
, p. 6417 - 6420 (2019)
An AIE dual-reactive supramolecular probe has been devised for the first time to simultaneously measure endogenous lipase and α-amylase activity in a homogeneous system. Fluorescence quantitative analysis of lipase and α-amylase in real biological samples enables rapid and accurate diagnosis of diseases.
The influence of intermolecular interactions and molecular packings on mechanochromism and mechanoluminescence-a tetraphenylethylene derivative case
Huang, Guangxi,Jiang, Yuqing,Wang, Jianguo,Li, Zhen,Li, Bing Shi,Tang, Ben Zhong
, p. 12709 - 12716 (2019)
Four tetraphenylethylene (TPE) derivatives 1-4 were synthesized to explore the influence of intermolecular interaction and molecular packing modes on their mechanochromism (MC) and mechanoluminescence (ML) performances. Compounds 1 and 2 modified with carboxyl groups had strong intermolecular interactions and were MC-active and ML-inactive, while compound 3 functionalized with a carboxyl ester had self-reversible MC and ML. Single crystal study of these molecules suggested that besides intermolecular interaction, molecular packing was also important for MC and ML properties. The carboxyl ester-modified 3c had weaker intermolecular interactions than 1c/2c, but it formed an intact three-dimensional hydrogen-bonded network and moderate packing density, which can efficiently block non-radiative relaxation and lead to ML. While 1c and 2c had strong molecular interactions, the molecular packing density in 1c was rather low due to its porous structure and 2c had a defective hydrogen-bonded network. These defective packings allowed non-radiative energy loss and inactivated the ML property of these two molecules.
A mechanistic study of AIE processes of TPE luminogens: Intramolecular rotation vs. configurational isomerization
Yang, Zhiyong,Qin, Wei,Leung, Nelson L. C.,Arseneault, Mathieu,Lam, Jacky W. Y.,Liang, Guodong,Sung, Herman H. Y.,Williams, Ian D.,Tang, Ben Zhong
, p. 99 - 107 (2015)
Chromophores containing olefinic double bonds are the core components of many important luminogen systems that show the novel photophysical effect of aggregation-induced emission (AIE). The role and extent of E-Z isomerization (EZI) of the double bond in affecting the solution emissions of the AIE luminogens (AIEgens), however, have not been fully understood. In this work, we verified the occurrence of EZI in the dilute solutions of TPE-cored AIEgens by NMR spectroscopy using elaborate experimental procedures. We further designed a TPE-fluorescein adduct to quantify that EZI plays a minor role whereas intramolecular rotation plays a major role in the emission quenching processes of the AIEgen solutions. This study fills the gap in the research on the restriction of the intramolecular rotation (RIR) mechanism for the AIE effect and provides a useful tool for the mechanistic investigation of photoluminescence processes.
Tetraphenylethylene-substituted tetraphenyl-porphyrin derivative and preparation method thereof
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Paragraph 0043; 0046; 0047; 0054; 0061, (2018/07/30)
The invention discloses a tetraphenylethylene-substituted tetraphenyl-porphyrin derivative. The structural formula of the tetraphenyl-porphyrin derivative is shown as a formula I. The invention also discloses a preparation method of the tetraphenylethylene-substituted tetraphenyl-porphyrin derivative. The preparation method comprises the following steps: firstly, preparing 4-(1,2,2-tristyrylphenol) benzoic acid; secondly, adding the 4-(1,2,2-tristyrylphenol) benzoic acid prepared in the first step, dicyclohexylcarbodiimide and p-N-N-dimethylpyridine into a dry organic solvent for stirring andactivating, then adding 5,10,15,20-tetra(4-hydroxyphenyl) porphyrin and p-toluenesulfonic acid and carrying out esterification reaction; after the reaction is finished, carrying out aftertreatment toobtain a product 5,10,15,20-tetra4{4-[4-(1,2,2-tristyrylphenol) ethopabate] phenyl}porphyrin. The tetraphenyl-porphyrin derivative still can emit stable red fluorescence in solid and poor solvents inan aggregation state, and the solid quantum yield can reach 7.5 percent; meanwhile, good thermal stability is achieved and the decomposition temperature is up to 455 DEG C. A preparation method provided by the invention is simple and feasible, and high yield is obtained. (The formula is shown in the description).
