333174-61-1Relevant articles and documents
Modulation of aggregation-induced emission and electroluminescence of silole derivatives by a covalent bonding pattern
Nie, Han,Chen, Bin,Quan, Changyun,Zhou, Jian,Qiu, Huayu,Hu, Rongrong,Su, Shi-Jian,Qin, Anjun,Zhao, Zujin,Tang, Ben Zhong
, p. 8137 - 8147 (2015)
The deciphering of structure-property relationships is of high importance to rational design of functional molecules and to explore their potential applications. In this work, a series of silole derivatives substituted with benzo[b]thiophene (BT) at the 2,5-positions of the silole ring are synthesized and characterized. The experimental investigation reveals that the covalent bonding through the 2-position of BT (2-BT) with silole ring allows a better conjugation of the backbone than that achieved though the 5-position of BT (5-BT), and results in totally different emission behaviors. The silole derivatives with 5-BT groups are weakly fluorescent in solutions, but are induced to emit intensely in aggregates, presenting excellent aggregation-induced emission (AIE) characteristics. Those with 2-BT groups can fluoresce more strongly in solutions, but no obvious emission enhancements are found in aggregates, suggesting they are not AIE-active. Theoretical calculations disclose that the good conjugation lowers the rotational motions of BT groups, which enables the molecules to emit more efficiently in solutions. But the well-conjugated planar backbone is prone to form strong intermoelcular interactions in aggregates, which decreases the emission efficiency. Non-doped organic light-emitting diodes (OLEDs) are fabricated by using these siloles as emitters. AIE-active silole derivatives show much better elecroluminescence properties than those without the AIE characterisic, demonstrating the advantage of AIE-active emitters in OLED applications. Stay connected! Connecting benzo[b]thiophene with a silole ring through its 2- or 5-position furnishes silole derivatives with totally different photoluminescence and electroluminescence properties (see figure).
2,5-difluorenyl-substituted siloles for the fabrication of high-performance yellow organic light-emitting diodes
Chen, Bin,Jiang, Yibin,Chen, Long,Nie, Han,He, Bairong,Lu, Ping,Sung, Herman H. Y.,Williams, Ian D.,Kwok, Hoi Sing,Qin, Anjun,Zhao, Zujin,Tang, Ben Zhong
, p. 1931 - 1939 (2014)
2,3,4,5-Tetraarylsiloles are a class of important luminogenic materials with efficient solid-state emission and excellent electron-transport capacity. However, those exhibiting outstanding electroluminescence properties are still rare. In this work, bulky 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, and 9,9-spirobifluorenyl substituents were introduced into the 2,5-positions of silole rings. The resulting 2,5-difluorenyl-substituted siloles are thermally stable and have low-lying LUMO energy levels. Crystallographic analysis revealed that intramolecular π-π interactions are prone to form between 9,9-spirobifluorene units and phenyl rings at the 3,4-positions of the silole ring. In the solution state, these new siloles show weak blue and green emission bands, arising from the fluorenyl groups and silole rings with a certain extension of π conjugation, respectively. With increasing substituent volume, intramolecular rotation is decreased, and thus the emissions of the present siloles gradually improved and they showed higher fluorescence quantum yields (ΦF=2.5-5.4 %) than 2,3,4,5-tetraphenylsiloles. They are highly emissive in solid films, with dominant green to yellow emissions and good solid-state ΦF values (75-88 %). Efficient organic light-emitting diodes were fabricated by adopting them as host emitters and gave high luminance, current efficiency, and power efficiency of up to 44 100cd m -2, 18.3cd A-1, and 15.7lm W-1, respectively. Notably, a maximum external quantum efficiency of 5.5 % was achieved in an optimized device.
Water-soluble AIE luminogens for monitoring and retardation of fibrillation of amyloid proteins
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, (2016/04/20)
Compounds that exhibit aggregation induced emission (AIE), and more particularly to water-soluble conjugated polyene compounds that exhibit aggregation induced emission. The conjugated polyene compounds can be used as bioprobes for DNA detection, G-quadru
Targeted theranostic platinum(IV) prodrug with a built-in aggregation-induced emission light-up apoptosis sensor for noninvasive early evaluation of its therapeutic responses in situ
Yuan, Youyong,Kwok, Ryan T. K.,Tang, Ben Zhong,Liu, Bin
supporting information, p. 2546 - 2554 (2014/03/21)
Targeted drug delivery to tumor cells with minimized side effects and real-time in situ monitoring of drug efficacy is highly desirable for personalized medicine. In this work, we report the synthesis and biological evaluation of a chemotherapeutic Pt(IV)
Creation of bifunctional materials: Improve electron-transporting ability of light emitters based on AIE-active 2,3,4,5-tetraphenylsiloles
Chen, Long,Jiang, Yibin,Nie, Han,Lu, Ping,Sung, Herman H. Y.,Williams, Ian D.,Kwok, Hoi Sing,Huang, Fei,Qin, Anjun,Zhao, Zujin,Tang, Ben Zhong
, p. 3621 - 3630 (2014/06/24)
2,3,4,5-Tetraphenylsiloles are excellent solid-state light emitters featured aggregation-induced emission (AIE) characteristics, but those that can efficiently function as both light-emitting and electron-transporting layers in one organic light-emitting diode (OLED) are much rare. To address this issue, herein, three tailored n-type light emitters comprised of 2,3,4,5- tetraphenylsilole and dimesitylboryl functional groups are designed and synthesized. The new siloles are fully characterized by standard spectroscopic and crystallographic methods with satisfactory results. Their thermal stabilities, electronic structures, photophysical properties, electrochemical behaviors and applications in OLEDs are investigated. These new siloles exhibit AIE characteristics with high emission efficiencies in solid films, and possess lower LUMO energy levels than their parents, 2,3,4,5-tetraphenylsiloles. The double-layer OLEDs [ITO/NPB (60 nm)/silole (60 nm)/LiF (1 nm)/Al (100 nm)] fabricated by adopting the new siloles as both light emitter and electron transporter afford excellent performances, with high electroluminescence efficiencies up to 13.9 cd A-1, 4.35% and 11.6 lm W-1, which are increased greatly relative to those attained from the triple-layer devices with an additional electron-transporting layer. These results demonstrate effective access to n-type solid-state emissive materials with practical utility. Grafting dimesitylboryl groups onto 2,3,4,5- tetraphenylsiloles generates efficient bifunctional materials that can simultaneously serve as light emitters and electron transporters in OLEDs. Remarkably high electroluminescence efficiencies up to 13.9 cd A-1, 4.35% and 11.6 lm W-1 are attained from the double-layer OLEDs based on them.
Synthesis of 2,5-substituted siloles and optical study of interactions with mercury(II), copper(II), and nickel(II) cations
Carroll, James B.,Braddock-Wilking, Janet
, p. 1905 - 1912 (2013/05/09)
Several 2,5-diaryl-1,1-dimethyl-3,4-diphenylsiloles (with aryl = p-cyanophenyl (1), m,p-bis(methylthio)phenyl (2), p-N,N-dimethylaminophenyl (3), 2,2′-bipyridin-6-yl (4)) were synthesized and characterized by UV-vis, fluorescence, and NMR spectroscopy, along with crystal structure determinations for 1 and 2. Compounds 1-4 in methylene chloride were combined with 1-10 equiv of M(ClO4)2 (M = Ni, Cu, Hg) in methanol, and the resulting solutions were monitored by UV-vis and fluorescence spectroscopy. Compound 1 showed slight effects for each metal, 2 exhibited fluorescence quenching selectively for Hg(II), 3 showed significant changes for all cations, and 4 generally demonstrated fluorescence quenching for all cations. A discussion of the causes behind these changes is also presented.
Aggregation Induced Emission Active Cytophilic Fluorescent Bioprobes for Long-Term Cell Tracking
-
Paragraph 0070-0075, (2013/04/13)
Fluorescent bioprobes comprising fluorogen formed nanoparticles comprising fluorogens with aggregation-induced emission (ATE) properties, which can be used for long-term cell tracking. The fluorogens are nonemissive in organic solution but become highly emissive when aggregated in aqueous solution. The fluorescent molecules can readily pass through cell membranes, stain only the cell cytoplasm, and form highly emissive nanoaggregates in aqueous media without any obvious cytoxicity in the living cells. Furthermore, the molecules can be retained inside the cells without noticeable leakage to the outside. Therefore, these ATE-based compounds can be used as selective and cell-compatible fluroescent bioprobes for long-term live cell tracking and imaging.
Naphthalene-substituted 2,3,4,5-tetraphenylsiloles: Synthesis, structure, aggregation-induced emission and efficient electroluminescence
Jiang, Tao,Jiang, Yibing,Qin, Wei,Chen, Shuming,Lu, Yahong,Lam, Jacky W.Y.,He, Bairong,Lu, Ping,Sung, Herman H.Y.,Williams, Ian D.,Kwok, Hoi Sing,Zhao, Zujin,Qiu, Huayu,Tang, Ben Zhong
, p. 20266 - 20272 (2013/02/23)
Two thermally stable naphthalene-substituted 2,3,4,5-tetraphenylsiloles, 1,1-dimethyl-2,5-bis[4-(naphthalen-1-yl)phenyl]-3,4-diphenylsilole (D-1-NpTPS) and 1,1-dimethyl-2,5-bis[4-(naphthalen-2-yl)phenyl]-3,4-diphenylsilole (D-2-NpTPS), have been synthesized and fully characterized. D-2-NpTPS shows redder absorption and emission than D-1-NpTPS due to the better conjugation between naphthalen-2-yl groups and phenyl rings at the 2,5-positions of the silole core. While they are weakly fluorescent in solutions, strong luminescence is induced when aggregated in poor solvents or fabricated into solid films, with high fluorescence quantum yields up to 99%, demonstrating their aggregation-induced emission (AIE) feature. Efficient non-doped organic light-emitting diodes utilizing D-1-NpTPS and D-2-NpTPS as light-emitting layers are fabricated. Remarkably high electroluminescence efficiencies of 10.5 cd A-1, 7.3 lm W-1, and 3.2% are acheived by the D-2-NpTPS device.
Synthesis of conjugated aryleneethynylenesiloles dendron
Liu, Jie,Yan, Chenxu,Li, Shanshan,Wang, Chengyun,Shen, Yongjia
, p. 2861 - 2868 (2013/08/23)
Three routes were designed to synthesize a π-conjugated aryleneethynylenesiloles dendron. With the desilylation of the disilole mono(silylethynyl) derivative in the presence of potassium carbonate (K 2CO3), the silole-containing oligomer has been successfully synthesized without impact on the Si-(CH3)2 group. The disilole mono(silylethynyl) derivative was prepared by means of the Sonogashira heterocoupling reaction between the diacetylene compound and asymmetrical silole, catalyzed by the dichloro bis(triphenylphosphine)palladium, in a divergent synthesis. Due to their steric effect and triethynylbenzene self-coupling Glaser reaction, the endeavour to prepare the dendron by controlling the molar ratio of asymmetrical silole and 1,3,5-triethynylbenzene was failed. The another attempt to prepare the dendron by different desilylation condition of triisopropylsilyl group and trimethylsilyl group was also failed, the desilylation of Si-(CH3)2 group in silacyclopentadiene unit was also easily accomplished in the presence of tetrabutylammonium fluoride(Bu4NF), whereas no reaction occurred when K 2CO3 was used instead of Bu4NF. Copyright
Hyperbranched conjugated polysiloles: Synthesis, structure, aggregation-enhanced emission, multicolor fluorescent photopatterning, and superamplified detection of explosives
Liu, Jianzhao,Zhong, Yongchun,Lam, Jacky W. Y.,Lu, Ping,Hong, Yuning,Yu, Yong,Yue, Yanan,Faisal, Mahtab,Sung, Herman H. Y.,Williams, Ian D.,Wong, Kam Sing,Tang, Ben Zhong
experimental part, p. 4921 - 4936 (2011/11/05)
Hyperbranched poly(2,5-silole)s [hb-P1(m), m = 1, 6] are synthesized for the first time in this work. 1,1-Dialkyl-2,5-bis(4-ethynylphenyl)-3,4- diphenylsiloles [1(m)] were polymerized by TaBr5, affording hb-P1(m) with high molecular weights (M
