1225493-18-4Relevant articles and documents
Smartly designed AIE triazoliums as unique targeting fluorescence tags for sulfonic biomacromolecule recognition: Via 'electrostatic locking'
Kang, Qing,Xiao, Yin,Hu, Wenping,Wang, Yong
, p. 12529 - 12536 (2018)
Specific electrostatic interactions are highly efficient for fluorescent bioassays but they are difficult to achieve. In this work, smartly designed aggregation-induced emission (AIE) triazoliums with donor-acceptor structures were developed via click conjugating a triazole heterocycle onto a tetraphenylethylene (TPE) fluorophore followed by a cationization reaction. The strongly electron-deficient nature of the triazolium coupled with intermolecular electrostatic repulsions resulted in the decrease of TPE's AIE character when it was in solution. However, specific electrostatic locking was found to take place between the triazolium and multiple sulfonates and this unique targeting combination attenuated triazolium's electrophilicity and electrostatic repulsion resulting in the recovery of the AIE. Cryo-electron microscopy (Cryo-EM) was used to reveal the in situ aggregation state of the probe. The triazolium probes exhibited a highly specific turn-on fluorescence response toward sulfonic biomacromolecules such as heparin, chondroitin and sulfonate cyclodextrin, demonstrating that the AIE-triazoliums have great potential for bioassay applications.
Meso Alkynylated Tetraphenylethylene (TPE) and 2,3,3-Triphenylacrylonitrile (TPAN) Substituted BODIPYs
Dhokale, Bhausaheb,Jadhav, Thaksen,Mobin, Shaikh M.,Misra, Rajneesh
, p. 8018 - 8025 (2015)
The tetraphenylethylene (TPE) substituted BODIPY 2a, and 2,3,3-triphenylacrylonitrile (TPAN) substituted BODIPYs 2b and 2c were designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling reaction. Their photophysical and electrochemical prope
Discotic liquid crystals with aggregation-induced emission properties based on tetraphenylethylene and triphenylene derivatives
Kong, Xiangfei,Luo, Ronggen,Gong, Hongkang,Chen, Dong,Yang, Shijun,Li, Shiqing,Wang, Guixia,He, Zhiqun
, p. 26 - 37 (2021)
A novel aggregation-induced emission active molecules (TP-Cn-PETPE, n = 4 and 10) were synthesized, which contain a tetraphenylethene derivative as the emission active moiety, a pentahexyloxytriphenylene core as the mesogenic unit and an alkoxy spacer. Ex
Color-tunable and highly solid emissive AIE molecules: Synthesis, photophysics, data storage and biological application
Li, Shuhong,Shang, Yanli,Zhao, Engui,Kwok, Ryan T. K.,Lam, Jacky W. Y.,Song, Yanlin,Tang, Ben Zhong
, p. 3445 - 3451 (2015)
In this work, several new compounds containing tetraphenylene (TPE) units and dimesitylboron groups were synthesized through Sonogashira coupling reaction. The compounds showed aggregation induced emission (AIE), emitted different colors and gave a relati
Halogen Bonding Tetraphenylethene Anion Receptors: Anion-Induced Emissive Aggregates and Photoswitchable Recognition
Beer, Paul D.,Davis, Jason J.,Docker, Andrew,Kuhn, Heike,Langton, Matthew J.,Shang, Xiaobo,Yuan, Daohe,Zhang, Zongyao
, p. 19442 - 19450 (2021/07/31)
A series of tetraphenylethene (TPE) derivatives functionalized with highly potent electron-deficient perfluoroaryl iodo-triazole halogen bond (XB) donors for anion recognition are reported. 1H NMR titration experiments, fluorescence spectroscopy, dynamic light scattering measurements, TEM imaging and X-ray crystal structure analysis reveal that the tetra-substituted halogen bonding receptor forms luminescent nanoscale aggregates, the formation of which is driven by XB-mediated anion coordination. This anion-coordination-induced aggregation effect serves as a powerful sensory mechanism, capable of luminescence chloride sensing at parts per billion concentration. Furthermore, the doubly substituted geometric isomers act as unprecedented photoswitchable XB donor anion receptors, where the composition of the photostationary state can be modulated by the presence of a coordinating halide anion.
D-π-A type tetraphenyl ethynylphenyl substituted pyridine conjugated luminous small molecule and synthesis method thereof
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Paragraph 0057; 0064, (2021/10/27)
The invention discloses D-π-A type tetraphenylethynylphenyl substituted pyridine conjugated luminous small molecule and a synthesis method thereof. 4 - Bromobenzaldehyde. The aryl acetophenone and ammonium acetate undergo Chichibabin reaction under the ca
Tetraphenylethylene alkyne phenyl alkoxy bridged alkoxy benzophenanthrene binary compound and preparation method thereof
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Paragraph 0036; 0058-0060, (2020/02/14)
The invention discloses a tetraphenylethylene alkyne phenyl alkoxy bridged alkoxy benzophenanthrene binary compound and a preparation method thereof. The compound is columnar phase in liquid crystal state and has aggregation-induced luminescence phenomeno
Intracellular Ruthenium-Promoted (2+2+2) Cycloadditions
Miguel-ávila, Joan,Tomás-Gamasa, María,Mascare?as, José L.
, p. 17628 - 17633 (2020/08/14)
Metal-mediated intracellular reactions are becoming invaluable tools in chemical and cell biology, and hold promise for strongly impacting the field of biomedicine. Most of the reactions reported so far involve either uncaging or redox processes. Demonstrated here for the first time is the viability of performing multicomponent alkyne cycloaromatizations inside live mammalian cells using ruthenium catalysts. Both fully intramolecular and intermolecular cycloadditions of diynes with alkynes are feasible, the latter providing an intracellular synthesis of appealing anthraquinones. The power of the approach is further demonstrated by generating anthraquinone AIEgens (AIE=aggregation induced emission) that otherwise do not go inside cells, and by modifying the intracellular distribution of the products by simply varying the type of ruthenium complex.
D-A-D type dinitriles with vapor-dependent luminescence in the solid state
Furuyama, Taniyuki,Shinozaki, Junichi,Tasso, Thiago Teixeira,Maeda, Hajime,Segi, Masahito,Kobayashi, Nagao
supporting information, p. 4243 - 4247 (2017/10/12)
D-A-D (Donor-Acceptor-Donor) type dinitriles linked by a styryl or phenylethynyl group have been prepared. These groups were introduced to increase the flexibility and the size of the π-conjugation in the chromophores. Both compounds showed strong emission in the solid state, AIE (aggregation-induced emission) behavior, and mechanochromism. The fluorescence color of ground powder changed by organic solvent vapor (vapochromism). Especially, the emission color of the styryl dinitrile after exposures depends on the solvent, while that of the phenylethynyl dinitrile is the same after exposure to different solvents. These results were explained by single crystal and powder XRD measurements, which revealed that the flexible styryl linker leads to a loose crystal packing, resulting in a dinitrile with multi-state microcrystalline structures. This methodology based on the flexible linker allows for the detection of small organic molecules without transition metals.
Synthesis and self-assembly of tetraphenylethene and biphenyl based AIE-active triazoles
Yuan, Wang Zhang,Mahtab, Faisal,Gong, Yongyang,Yu, Zhen-Qiang,Lu, Ping,Tang, Youhong,Lam, Jacky W. Y.,Zhu, Caizhen,Tang, Ben Zhong
, p. 10472 - 10479 (2012/08/13)
Self-assembly of fluorescent functional materials has attracted increasing interest in the fabrication of optoelectronic and biological nanodevices. Tetraphenylethene (TPE) is a typical dye molecule with aggregation-induced- emission (AIE) characteristics. Melding TPE carrying triple-bond functionality with diazide-containing biphenyl through "click" chemistry generates AIE-active luminogens [1,1′-biphenyl]-4,4′-diyl bis(6-(4-(4-(1,2,2- triphenylvinyl)phenyl)-1H-1,2,3-triazol-1-yl) hexanoate) [1(5)] and [1,1′-biphenyl]-4,4′-diyl bis(11-(4-(4-(1,2,2-triphenylvinyl)phenyl) -1H-1,2,3-triazol-1-yl) undecanoate) [1(10)] with solid state efficiencies up to unity. Slow addition of dilute THF solutions of 1(m) (m = 5, 10) into nonsolvents such as n-hexane and water yields self-assembled white wooly solids. TEM and SEM observations reveal the (helical) nanofibrous structure of the aggregates. Upon cooling from their concentrated hot solutions, 1(m) readily precipitate. Meanwhile, they can also form gels at high concentrations. Both precipitates and gels of 1(m) exhibit structures similar to those of the aggregates formed in nonsolvents. These results indicate that 1(m) can facilely self-assemble into high emission efficiency (helical) nanofibers, thus paving the way for their optoelectronic and biological applications. The Royal Society of Chemistry 2012.
