Chengyun Wang

East China University of Science and Technology, Shanghai, Shanghai Shi, China

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Publications (33)70.49 Total impact

  • Rui Huang · Panpan Zou · Qisong Zhang · Chengyun Wang · Yongjia Shen
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    ABSTRACT: Monomer 5 was designed and synthesized via Steglich esterification reaction by connecting 3, 4-propylenedioxythiophene methanol (2) and derivative of tetrathiafulvalene (3). The structure was characterized by EI-MS, 1H NMR and elemental analysis. Its behavior and performance were studied via comparison to monomer 4. The result indicated that the intramolecular charge transfer of 5 was greatly inhibited due to the broadened band gap as well as the twisted plane of the molecule.
    No preview · Article · Feb 2016 · Microelectronic Engineering
  • Qisong Zhang · Jian Zhang · Hujin Zuo · Chengyun Wang · Yongjia Shen
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    ABSTRACT: A chemical sensor containing triphenylamine and benzothiadiazole for cyanide anions detection was designed and synthesized, whose structural feature is a donor-acceptor-donor (D-A-D) molecular configuration, which is substituted with a dicyanovinyl group served as a sensing unit. The nucleophilic addition of cyanide ion to the dicyanovinyl moiety was activated in the principle of Michael addition, which broken the electron-withdrawing interaction of dicyanovinyl moiety. The obstruction in the intramolecular charge transfer (ICT) induced remarkable changes in the absorption and emission spectra. The sensor exhibited splendid selectivity and anti-interference performance towards CN- over other anions (F-, Cl-, Br-, I-, NO2-, NO3-, HCO3-, H2PO4-, HS-, HSO3-, NCO-, SCN-, SO32-, SO42-, HPO42-, CO32-). The mechanism was investigated by absorption and emission spectra together with 1H-NMR titration.
    No preview · Article · Jan 2016
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    ABSTRACT: This paper reports the self-assembly of two new tetrathiafulvalene (TTF) derivatives that contain one or two urethane groups. The formation of nanoribbons was evidenced by scanning electron microscopy (SEM) and X-ray diffraction (XRD), which showed that the self-assembly ability of T 1 was better than that of T 2 . The results revealed that more urethane groups in a molecule did not necessarily instigate self-assembly. UV-vis and FTIR spectra were measured to explore noncovalent interactions. The driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and π-π stacking interactions. The electronic conductivity of the T 1 and T 2 films was tested by a four-probe method.
    Preview · Article · Nov 2015 · Beilstein Journal of Organic Chemistry
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    ABSTRACT: In view of palladium contaminants and their adverse effects on human health, it is valuable to develop an effective probe for palladium. In this work, a coumarin-based colorimetric and turn-on fluorescent probe, Cou-1, for highly selective and sensitive detection of palladium was designed based on the Tsuji-Trost allylic reaction. Upon the addition of palladium to the solution of probe, the probe gave an emission peak at around 498 nm as well as displayed a selective chromogenic behavior toward palladium from colorless to yellow-green, which could be easily observed by the naked eye. Moreover, compared with typical transition metal cations and other common cations used, Cou-1 showed great selectivity toward palladium. Further, the detection limit toward palladium was calculated to be as low as 17.4 nM.
    No preview · Article · Oct 2015 · Tetrahedron
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    ABSTRACT: Two novel 2,1,3-benzothiadiazole derivatives, used as colorimetric and fluorescent sensors for fluoride ion were designed, synthesized and characterized. These sensors contained single hydrogen-bond functional groups, which acted as interacting sites for fluoride ion. Both sensors displayed a red color in dimethyl sulfoxide solution. Binding studies revealed that they showed noticeable colorimetric and fluorescent responses only to F- among the eight anions tested (F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4- and NO3-). 1H NMR titration proved that the interaction between compounds and fluoride ion: hydrogen bond at low fluoride ion concentration, deprotonation at high fluoride ion concentration. Moreover, those compounds showed high sensitivity and selectivity for fluoride ion by inhibiting the excited state intramolecular proton transfer processes, and the detective processes could be followed by direct visual observation.
    No preview · Article · Sep 2015 · Dyes and Pigments
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    Jian Sun · Zheming Jin · Chengyun Wang · Yongjia Shen
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    ABSTRACT: Three bis-1,2-dithiolene nickel complexes with unsaturated substituted groups in the terminals, bis[4,5-di(4'-t-butylbenzyl)thio-1,3-dithion]nickel (2a), bis[4,5-dially-thio-1,3-dithion]nickel (2b) and bis[4,5-di(3'-phenyl-ally)thio-1,3-di-thion]nickel (2c) together with a bis-1,2-dithiolene nickel complexes with saturated substituted groups in the terminals, bis[4,5-didecylthio-1,3-dithion]nickel (2d), as a reference, were synthesized and characterized by 1H NMR and MS. They were easily soluble in toluene with the maximum absorption wavelengths (λmax) around 1000 nm, the effects of substituent groups in the terminals on λmax were not so significant. Their λmax in solid polymethyl methacrylate (PMMA) were around 1000 nm as well, and no broadening absorption bands could be observed in lower concentration. The solid cyclic voltammetry (CV) curves showed that the oxidation potentials would be increased by introduction of phenyl group in the terminals, thus their electrochemical stability could be improved. The results of thermal gravimetric analysis (TGA) indicated that the temperature of 5% weight-loss was higher than 200℃ for these compounds. Irradiated by xenon lamp (300 W) for 100 min, their absorbance was decreased less than 100% in toluene and 2% in solid polymethyl methacrylate (PMMA), respectively. The introduction of phenyl group in the terminals could improve the photo-stability for these molecules both in solution and solid PMMA.
    Preview · Article · Sep 2015 · Chinese Journal of Organic Chemistry
  • Yuwen Ma · Guoqiao Lai · Zhifang Li · Wenbin Tan · Yongjia Shen · Chengyun Wang
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    ABSTRACT: Two novel donor-π-acceptor chemosensors, exTTF-DPA and exTTF-ADPA, based on π-extended tetrathiafulvalene (exTTF) and di(pyridine-2-ylmethyl)amine (DPA) were synthesized and used as optical and electrochemical chemosensors for copper(II). The results showed that they possess specific selectivity for copper(II) in the presence of other competing metal ions (Zn2+, Sn2+, Pb2+, Pd2+, Hg2+, Al3+, Fe3+, Ag+, Co2+, Ni2+) in acetonitrile. Upon the addition of Cu2+, the solution color changed from yellow to orange, the cyclic voltammograms changed dramatically and the fluorescence quenched completely.
    No preview · Article · Sep 2015 · Tetrahedron
  • Rui Huang · Hujin Zuo · Lei Zhang · Chengyun Wang · Yongjia Shen
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    ABSTRACT: Two copolymers (P1 and P2), bearing 3,4-ethylenedioxythiophene and fluorene moieties, were synthesized via Sonogashira coupling reaction successfully and P2 contains additional tetrathiafulvalene derivatives (TTFs) as pendants. The structures and properties of copolymer P1 and P2 were investigated by Infrared spectra, UV–visible spectra, and fluorescence spectra. Spectra analyses revealed that the fluorescent intensity of P2 was only 2 % compared to that of P1 in solution. The quenched fluorescent intensity of P2 could be recovered after adding defined moles of Fe(ClO4)3 as an oxidant. The phenomenon was discussed with aid of computational stimulation in Gaussian 03. Herein, it is believed that intramolecular charge transfer occurs between TTF pendants and polymeric backbone in P2. P2 could be treated as a reporting group in fluorescent testing/switching system. Graphical abstract
    No preview · Article · Jun 2015 · Polymer Bulletin
  • Yingyi Wang · Guoqiao Lai · Zhifang Li · Yuwen Ma · Yongjia Shen · Chengyun Wang
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    ABSTRACT: A series of new A–π–D–π–A molecules including diphenylamine and carbazole had been synthesized and characterized (T1–T3). T1 and T2 displayed aggregation-induced emission enhancement (AIEE): exhibiting weak fluorescence in pure THF, which a signification AIEE effect was observed in mixture with a water fraction (fw) of 90% with a sharp increase in fluorescence intensity. T3 displayed aggregation-caused quenching (ACQ): exhibiting strong fluorescence in pure THF, which a signification ACQ effect was observed in mixture with a water fraction (fw) of 90% with a sharp decrease in fluorescence intensity. Their two-photon absorption (2PA) had been investigated using the open-aperture Z-scan technique, and the values of the 2PA cross section at 800 nm for T1–T3 were 1115, 681, in chloroform, respectively.
    No preview · Article · May 2015 · Tetrahedron
  • Zhenhua He · Guoqiao Lai · Zhifang Li · Xiao Yuan · Yongjia Shen · Chengyun Wang
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    ABSTRACT: Two copolymers, poly(1,1-dimethyl-3,4-diphenylsilole-alt-N-hexyl-3,6-diethynylcarbazole) (PS-DyCz) and poly(1,1-dimethyl-3,4-diphenylsilole-alt-2,7-diethynyl-9,9′-dihexylfluorene) (PS-DyF), were synthesized by Sonogashira coupling reaction of 2,5-dibromo-1,1-dimethyl-3,4-diphenylsilole and N-hexyl-3,6-diethynylcarbazole or 2,7-diethynyl-9,9′-dihexylfluorene, respectively. The chemical structures of the copolymers were characterized by NMR, FT-IR techniques. Their thermal and photophysical properties were evaluated by TGA, DSC, UV-Vis and fluorescence spectroscopy, respectively. The weight-averaged molecular weights (Mw) of PS-DyCz and PS-DyF are 1.20×104 and 3.83×104 Da, respectively. The degree of polymerization is 8 and 22 units. These π-conjugated polymers exhibited lower band-gap of 2.25 and 2.70 eV due to the presence of silole rings and CC triple bonds in their backbone, the results were consistent with the density functional (DFT) calculations at the B3LYP/6-31G* level.
    No preview · Article · Mar 2015 · Chinese Journal of Chemistry
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    ABSTRACT: New donor-linker-acceptor pattern organic dye containing a dithienosilole unit as a pi-conjugated system, a carbazole moiety as an electron donor, and a cyanoacrylic acid unit as an electron acceptor was synthesized for application in dye-sensitized solar cell (DSSC). Its photophysical and electrochemical properties were investigated, the dithienosilole unit could dramatically lower the lowest unoccupied molecular orbital (LUMO) level and energy gap. Its performances as sensitizers in solar cells were measured, and possessed a power conversion efficiency of 4.80%.
    No preview · Article · Nov 2014 · Journal of Photochemistry and Photobiology A Chemistry
  • Lei Zhang · Changzhi Wu · Chengyun Wang · Hujin Zuo · Yongjia Shen
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    ABSTRACT: 3,4-(Hydroxymethyl-ethylenedioxy)thiophene (4) and 3,4-(2-hydroxypropylenedioxy)thiophene (4') were synthesized from dimethyl 3,4-dihydroxythiophene-2,5-dicarboxylate (1), which were isomers and difficult to separate. When they were esterified with tetrathiafulvalene carried carboxylic acid group, only 3,4-(hydroxymethyl-ethylenedioxy)thiophene (4) could be esterified. No such selectivity was observed when the isomers were esterified by lauric acid and benzoic acid, respectively.
    No preview · Article · Sep 2014 · Journal of Heterocyclic Chemistry
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    ABSTRACT: Reaction between 3,3′-dibromothiophene and sodium methylate/methanol in the presence of KI/CuO afforded 3-bromo-4-methoxythiophene as a major product. It was transformed into 4,4′-dimethoxy-3,3′-bithiophene by using Pd(OAc)2 as a catalyst and agarose as a ligand. The conditions of the reaction were mild with an acceptable yield of 20 %. The product was characterized by MS, 1H NMR, and its spectra of UV–Vis and cyclic voltammetry were given. Graphical Abstract 4,4′-dimethoxy-3,3′-bithiophene was synthesized from 3-bromo-4-methyloxy thiophene in the homogeneous system formed by water and agarose.
    No preview · Article · Jul 2014 · Research on Chemical Intermediates
  • Songyang Jiang · Yuwen Ma · Yingyi Wang · Chengyun Wang · Yongjia Shen
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    ABSTRACT: Two conjugated ethynyl-linked oligomers, oligo(benzodithiophene-ethynylene-benzothiadiazole) (O1) and oligo(benzodithiophene-ethynylene-carbazole) (O2), were synthesized by Sonogashira coupling reaction. Their degrees of polymerization were 7 and 10, respectively. Their photophysical and electrochemical properties were investigated. O1 exhibitd two strong absorption bands at 404 nm and 483 nm, and O2 at 401 nm and 429 nm. The results of UV-Vis, cyclic voltammetry (CV) and theoretical calculations showed that O1 has a narrower band gap than O2. The conductivities of O1 and O2 were 1.05×10−15 and 6.98×10−16 S/cm, respectively, and would increase to 1.23×10−10 and 1.05×10−10 S/cm after doping with iodine.
    No preview · Article · Apr 2014 · Chinese Journal of Chemistry
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    ABSTRACT: Two new dye sensitizers 5-(N,N-4-(diphenylamino)phenyl)-10-(4-(tert-butyl-2-cyanoacrylate)phenyl)porphyrin (TP) and 5-(N, N-4-(bis(4-butylphenyl) amino) phenyl)-10-(4-(tert-butyl-2-cyanoacrylate)phenyl)porphyrin (BUTP) with cyanoacrylic acid as electron acceptor were synthesized and researched. BUTP has strong absorption in a wide range of 300–726 nm. DSSCs sensitized by BUTP displayed a power conversion efficiency (η) 5.33%, JSC 12.21 mA cm−2, Voc 0.68 V, FF 0.65, under the illumination of AM 1.5 G. Spectral properties, electrochemical properties, photovoltaic and electrochemical impedance properties of TP and BUTP were also investigated. Considering its simple synthesis, both TP and BUTP were qualified sensitizers for DSSCs.
    No preview · Article · Nov 2013 · Journal of Photochemistry and Photobiology A Chemistry
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    ABSTRACT: A new conjugated copolymer (PTST-DyOXD) derived from 1,1-dimethyl-3,4-diphenyl-2,5-bis(5-bromo-2-thienyl)-silole (TST) and 2,5-bis(4-ethynylphenyl)-1,3,4-oxadiazole (DyOXD) was synthesized by Pd(0)-catalyzed Sonogashira coupling reaction. For comparison, another copolymer without acetenyl group (PTST-OXD) was also synthesized by Pd(0)-catalyzed Suzuki coupling reaction. Chemical structures and optoelectronic properties of the copolymers were characterized by 1H NMR, 13C NMR, IR, UV-vis absorption, photoluminescence and cyclic voltammetry. The number-average molecular weight (Mn) is 4010 Da for PTST-DyOXD and 3890 Da for PTST-OXD, respectively. The thermogravimetric analysis (TGA) measurements show that they have good thermal stability with decomposition temperature at 312 and 318°C, respectively. The optical band gap is 2.21 eV for PTST-DyOXD and 2.10 eV for PTST-OXD based on the absorption onset. CV analysis revealed the LUMO level of PTST-DyOXD is −3.04 eV, lower than that of PTST-OXD (about −2.89 eV), which is attributed to the introduction of acetylene group in PTST-DyOXD, increasing the system of the conjugate chain length.
    No preview · Article · Jun 2013 · Chinese Journal of Chemistry
  • Lei Zhang · Meijiang Li · Chengyun Wang · Yanhong Wang · Yongjia Shen
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    ABSTRACT: Three 3,4‐ethylenedioxythiophene (EDOT) derivatives, including an EDOT‐tetrathiafulvalene (TTF) derivative, were synthesized by Steglich esterification of carboxylic acids with hydroxymethyl EDOT (3,4‐ethylenedioxythiophene methanol). The UV spectra showed that there was no distinctive intramolecular interaction for the EDOT–TTF monomer between the EDOT and the TTF moieties in the ground state; however, the cyclic voltammetry responses implied that such intramolecular interaction occurred. Electropolymerization in excessive potential could bring in strong overoxidation effects and degradation in the polymer film. The polymers were simulated using density functional theory with Gaussian03 package and the optimized HOMO and LUMO state were figured out. The conductivity of TTF‐polymer was 6 S·cm−1 obtained by galvano station and 4.8 × 10−3 S·cm−1 obtained by potentiostatic electropolymerization after doping with 7,7,8,8‐tetracyanoquinodimethane. The results indicated that this polymer was a reasonable candidate for conducting materials and it was meaningful to increase the conductive dimensions of TTF polymers by chemical doping. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013
    No preview · Article · Mar 2013 · Journal of Applied Polymer Science
  • Jie Liu · Chenxu Yan · Shanshan Li · Chengyun Wang · Yongjia Shen
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    ABSTRACT: 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 (K2CO3), 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 K2CO3 was used instead of Bu4NF.
    No preview · Article · Dec 2012 · Chinese Journal of Chemistry
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    Qiuyan Chen · Yuwen Ma · Chengyun Wang · Yongjia Shen
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    ABSTRACT: Several synthetic routes were designed to prepare 1,3,5-tris[(4-ethynylphenyl)ethynyl]benzene. The synthetic routes and reaction conditions were contrasted and discussed, when multiple Sonogashira reactions were occurred between multifunctional alkyne-terminal compounds and aromatic bromine compounds, the different substitution degree compounds with similar polarity were obtained, and they were difficult to separate. Whereas the reactions between multifunctional alkyne-terminal compounds and aromatic iodine compounds can avoid this situation. 1,3,5-Tribromobenzene reacted with 3-methylbutynol to afford 1,3,5-tris(3'-hydroxy-3'-methyl-but-1'-ynyl)benzene, then 1,3,5-triethynylbenzene was obtained by the cleavage reaction of the compound in presence of potassium hydroxide and toluene. On the other hand, using 4-iodoaniline and trimethyl silyl acetylene as raw materials, 4-trimethylsiylethynyl iodobenzene was synthesized by diazo reaction and halogenation. Therefore, 1,3,5-tris[(4'-ethynylphenyl)ethynyl]benzene was prepared by the cleavage reaction of the 1,3,5-triethynylbenzene and 4-trimethylsiylethynyl iodobenzene. The structures of the target compound and intermediates were confirmed by H-1 NMR, C-13 NMR techniques and element analysis.
    Preview · Article · Aug 2012 · Chinese Journal of Organic Chemistry
  • Weifu Shu · Changwei Guan · Wenhao Guo · Chengyun Wang · Yongjia Shen
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    ABSTRACT: Hyperbranched and linear conjugated polysiloles incorporating arylene ethynylene subunits (6 and 7) were synthesized by the Sonogashira reaction. The two polymers possess unusual phenomena of PL, with gradual addition of water in their THF solution, the intensity of PL firstly increased and then decreased, this may be due to the aggregate-enhanced emission (AEE) effect and aggregation-caused quenching (ACQ) effect. The polymers function as sensitive fluorescent chemosensors for the detection of explosives, such as picric acid (PA) and TNT. The quenching constants of 6 for PA and TNT were 4.7 × 10−2 ppm−1 and 4.6 × 10−3 ppm−1, respectively. The quenching constants of 7 for PA and TNT were 8.6 × 10−2 ppm−1 and 6.5 × 10−3 ppm−1 respectively. The polymer7 has more detective efficiency for PA and TNT than that of polymer6, this may be due to the less steric hindrance.
    No preview · Article · Jan 2012 · Journal of Materials Chemistry