Zhao-yang Wang

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Organization: South China Normal University
Department: School of Chemistry and Environment
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Co-reporter:Jingpei Huo, Zhudong Hu, Dongchu Chen, Shihe Luo, Zhaoyang Wang, Yonghui Gao, Min Zhang, and Hong Chen
ACS Omega September 2017? Volume 2(Issue 9) pp:5557-5557
Publication Date(Web):September 7, 2017
DOI:10.1021/acsomega.7b00196
A series of novel heterocyclic polymers with fluorescent brightening properties are synthesized via Click polymerization. Fast synthesis of poly-1,2,3-triazoles (Mn ≥ 9.31 kDa) is described herein, with a high yield of up to 95%. The Click polymerization approach has a number of advantages, including facile operation and outstanding isolation yield. The resultant polymers have a high thermal stability, excellent UV resistance, as well as acid and light fastness. On embedding with optical brightening agents, the polymers display strong fluorescent brightening properties in the tetrahydrofuran solution. Moreover, these products have a strong solution emission intensity and extraordinary photostability under UV light.Topics: Fibers; Fluorescence; Optical materials; Optical properties; Physical and chemical processes; Polyesters; Solubility; Thermal properties;
Co-reporter:Liang Cao;Shi-He Luo;Han-Qing Wu;Liu-Qing Chen;Kai Jiang;Zhi-Feng Hao
Advanced Synthesis & Catalysis 2017 Volume 359(Issue 17) pp:2961-2971
Publication Date(Web):2017/09/04
DOI:10.1002/adsc.201700600
AbstractAn efficient copper(I)/proline sodium salt-catalyzed alkyl- and arylsulfenylation of C(sp2)–X 3,4-dihalo-2(5H)-furanone compounds with sulfoxides is described. For inexpensive C(sp2)–Cl compounds, there is also a satisfactory reactivity with the moderate yields. This transformation provides a novel approach for the utilization of sulfoxides (not only DMSO) as sulfur source at mild temperatures without the need for an anaerobic atmosphere. More importantly, both sulfoxide and proline sodium salt can play a dual role in this reaction.
Co-reporter:Yan-Cheng Wu, Shi-He Luo, Wen-Jie Mei, Liang Cao, Han-Qing Wu, Zhao-Yang Wang
European Journal of Medicinal Chemistry 2017 Volume 139(Volume 139) pp:
Publication Date(Web):20 October 2017
DOI:10.1016/j.ejmech.2017.08.005
•A simple method without metal catalyst for synthesis of 2(5H)-furanone derivatives.•Compound 3j exhibits significant inhibitory activity against MCF-7 cell.•Compound 3j can induce cell cycle arrest at G2/M phase in MCF-7 cells.•Compound 3j has stronger binding affinity to c-myc G4 DNA than compound 3e.An efficient route without metal catalyst has been developed for synthesis of 4-biphenylamino-5-halo-2(5H)-furanones. The antitumor activities against various tumor cells of all the compounds have been evaluated by MTT assay. Among them, the compound 3j exhibits significant inhibitory activity against MCF-7 human breast cancer cells with an IC50 value of 11.8 μM and low toxicity toward HaCaT human normal cells. The mechanism studies confirm that 3j can induce cell cycle arrest at G2/M phase in MCF-7 cells. Compared with compound 3e, 3j has stronger binding affinity to c-myc G-quadruplex (G4) DNA via π-π stacking and H-bonding interactions. Western blot analysis also further confirms that compound 3j can down-regulate the expression of c-myc in MCF-7 cells.Download high-res image (281KB)Download full-size image
Co-reporter:Yan-Cheng Wu, Jia-Yi You, Kai Jiang, Jie-Chun Xie, Shu-Li Li, Derong Cao, Zhao-Yang Wang
Dyes and Pigments 2017 Volume 140(Volume 140) pp:
Publication Date(Web):1 May 2017
DOI:10.1016/j.dyepig.2017.01.025
•Simple metal-free synthesis of a novel benzimidazole-naphthalene conjugate molecule.•A ratiometric and colorimetric dual-channel fluorescent sensor for F− is developed.•Sensor 4 can be reversible and reusable for sensing F− in presence of H+.•Sensor 4 can be developed as an INHIBIT type logic gate at molecular level.•It is practically applied to detect F− from inorganic origin and in solid state.A novel benzimidazole-naphthalene conjugate molecule has been successfully designed and applied as a colorimetric and ratiometric fluorescent sensor for direct visual detection of F− with high selectivity over other anions. Addition of F− to the sensor resulted in an obvious color change from colorless to pale green under ambient light and blue to green under 365 nm UV light, respectively. 1H NMR and DFT calculations studies confirm that the recognition towards F− is due to the formation of an NH⋯F hydrogen bond and subsequent deprotonation. In addition, the sensor can be reversible and reusable for sensing fluoride ion in the presence of H+, thus it can be developed as an INHIBIT type logic gate at molecular level. Moreover, the sensor with high sensitivity and fast response has also been successfully applied to the detection of F− from inorganic origins and in the solid state.Download high-res image (414KB)Download full-size image
Co-reporter:Yan-Cheng Wu, Shi-He Luo, Liang Cao, Kai Jiang, Ling-Yun Wang, Jie-Chun Xie, Zhao-Yang Wang
Analytica Chimica Acta 2017 Volume 976(Volume 976) pp:
Publication Date(Web):11 July 2017
DOI:10.1016/j.aca.2017.04.022
•A novel sensor for ultrasensitive detection of PA in aqueous media by dual mechanism.•The limit of detection of sensor 4 is as low as 0.57 ppb PA in aqueous media.•Sensor 4 can detect PA as highly sensitive as 11.46 ag cm−2 by contact mode.•It is practically applicable for sensing PA in real samples and vapor phase.A 2,6-dibenzimidazole-appended naphthalene derivative flanking with two N-alkyl chains (sensor 4) was designed and applied for highly sensitive detection of picric acid (PA) in aqueous media. Driven by the hydrophobicity of alkyl chain and π-π stacking effect of aryl, sensor 4 can undergo self-assembly to form an orderly rod-like structure in H2O/THF (v/v, 90/10) solution, as shown by the dynamic light scattering (DLS) and scanning electron microscopy (SEM) studies. Sensor 4 shows high selectivity and sensitivity toward PA over other nitroaromatic explosives. DFT calculations and 1H NMR, the time-correlated single photon counting (TCSPC) experiments confirm that the quenching mechanism is due to both electron and energy transfer from the electron-rich sensor 4 to the electron-deficient PA. Sensor 4 can detect as low as 0.57 ppb PA in aqueous media and 11.46 ag cm−2 PA by contact mode. Importantly, sensor 4 exhibits low interference against common solvents, metal ions and anions. Thus, it is practically applicable for sensing PA in real environmental samples and vapor phase.Download high-res image (238KB)Download full-size image
Co-reporter:Shi-He Luo;Yan-Cheng Wu;Liang Cao;Qun-Fang Wang;Shui-Xia Chen;Zhi-Feng Hao;Le Jing
Polymer Chemistry (2010-Present) 2017 vol. 8(Issue 45) pp:7009-7016
Publication Date(Web):2017/11/21
DOI:10.1039/C7PY01213F
A series of polylactic acid-ibuprofen (PLA-IBU) conjugates was directly synthesized via melt polycondensation of lactic acid (LA) with ibuprofen (IBU) in the presence of 0.3 wt% SnO at 160 °C for 6 h. The structures of the PLA-IBU conjugates were confirmed by FTIR and 1H NMR. According to the GPC and DSC results, the molecular weight and Tg of the PLA-IBUs with different feed ratios increase as the feed amount of LA increases. The drug content of these IBU-conjugated biodegradable polymers can also be simply controlled by adjusting the monomer feed ratio to reach the expected levels. The preliminary biological tests show that the PLA-IBU conjugates have the anticipated pharmaceutical activity, which is beneficial for these PLA-based IBU prodrugs prepared by this convenient one-pot method to be efficiently used in the biochemical and pharmaceutical industry.
Co-reporter:Jingpei Huo;Qianjun Deng;Ting Fan;Guozhang He;Xiaohong Hu;Xiaxiao Hong;Hong Chen;Shihe Luo;Zhaoyang Wang;Dongchu Chen
Polymer Chemistry (2010-Present) 2017 vol. 8(Issue 48) pp:7438-7445
Publication Date(Web):2017/12/12
DOI:10.1039/C7PY01396E
As a kind of smart material, polydiacetylene (PDA) has a unique conjugated structure, providing a powerful tool for building the diversity of the chemical structure, applying for different sensors. This review focuses on various side chain groups based on PDAs published over the last 3 years, covering urea, melamine, ferriferous oxide and coumarin. Perspectives on the remaining challenges and future developments are also proposed.
Co-reporter:Jie Shi, Xiao-Dong Tang, Yan-Cheng Wu, Jie-Fang Fang, Liang Cao, Xiao-Yun Chen and Zhao-Yang Wang  
RSC Advances 2016 vol. 6(Issue 31) pp:25651-25655
Publication Date(Web):02 Mar 2016
DOI:10.1039/C6RA01393G
A radical coupling reaction of DMSO with sodium arylsulfinates under air atmosphere to afford arylsulfonyl dibromomethane is described. This transformation provides a novel approach for the utilization of DMSO as a C1 resource with mild temperature without the need for an anaerobic atmosphere.
Co-reporter:Jie Shi;Xiao-Dong Tang;Yan-Cheng Wu;Hua-Nv Li;Liu-Juan Song
European Journal of Organic Chemistry 2015 Volume 2015( Issue 6) pp:1193-1197
Publication Date(Web):
DOI:10.1002/ejoc.201403404

Abstract

A palladium-catalyzed desulfitative arylation reaction of 5-alkoxy-3,4-dibromo-2(5H)-furanones to provide 5-alkoxy-4-aryl-3-bromo-2(5H)-furanones is reported. This reaction has a high reaction site selectivity, which can realize arylation at the C4-position. Various sodium arylsulfinates are well tolerated under the mild reaction conditions. The current study makes the arylation of general alkenyl halides possible by the use of cheap and easily available sodium arylsulfinates as aryl sources.

Co-reporter:Jin-Feng Xiong;Qun-Fang Wang;Pai Peng;Jie Shi;Chong-ling Yang
Journal of Applied Polymer Science 2014 Volume 131( Issue 10) pp:
Publication Date(Web):
DOI:10.1002/app.40275

ABSTRACT

Directly starting from d,l-lactic acid (LA) and pyrimidine-2,4,5,6-tetramine (PTA), the copolymer P(LA-co-PTA) as a novel potential solid compatible polymeric flame retardant is synthesized as designed via melt polycondensation. When the molar feed ratio LA/PTA is 60/1, the optimal synthetic conditions are discussed. After the prepolymerization at 140°C for 8 h, using 0.5 wt % stannous oxide as the catalyst, the melt copolymerization at 160°C for 4 h gives the copolymer with the biggest intrinsic viscosity 0.88 dL g−1. The structures and properties of P(LA-co-PTA)s at different molar feed ratios are characterized by FT-IR, 1H-NMR, 13C-NMR, GPC, XRD, DSC, and TGA. The decomposition temperatures of P(LA-co-PTA)s are higher than these of homopolymer poly(d,l-lactic acid) (PDLLA). All copolymers have higher char yield than PDLLA, and the more PTA in the feed content, the higher char yield. What's more, there are some residues at 700–800°C, indicating that P(LA-co-PTA)s have good charring ability. When the monomer PTA is introduced into polylactic acid by chemical bonding as purine (PU) unit formed during the condensation, both the PTA's relatively higher nitrogen content and the PU's similar structure with flame retardant benzimidazole are beneficial to improve the thermal stability and charring ability, especially the latter. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40275.

Co-reporter:Jin-Feng Xiong, Shi-He Luo, Jing-Pei Huo, Jin-Yan Liu, Shui-Xia Chen, and Zhao-Yang Wang
The Journal of Organic Chemistry 2014 Volume 79(Issue 17) pp:8366-8373
Publication Date(Web):August 14, 2014
DOI:10.1021/jo5016954
A new kind of supramolecular columnar liquid crystal T–A with a broad mesomorphic range (up to 164.9 °C), good thermal stability, and strong fluorescence is designed and formed by the H-bonding between 1,3,5-tri(1H-benzo[d]imidazol-2-yl)benzene (T) and serial gallic acid derivatives (A). Two components are easily available because of simple routes, common reactions, high yields, commercial starting materials, and inexpensive catalysts. The introduction of the 1,2,3-triazole structure into component A makes the textures different and is slightly disadvantageous for the T–A complexes.
Co-reporter:Jin-Feng Xiong, Jian-Xiao Li, Guang-Zhen Mo, Jing-Pei Huo, Jin-Yan Liu, Xiao-Yun Chen, and Zhao-Yang Wang
The Journal of Organic Chemistry 2014 Volume 79(Issue 23) pp:11619-11630
Publication Date(Web):November 11, 2014
DOI:10.1021/jo502281b
1,3,5-Tri(1H-benzo[d]imidazol-2-yl)benzene derivatives, as a new kind of fluorescent chemosensor for the detection of nitroaromatic explosives, are designed and synthesized by simple N-hydrocarbylation. Among 16 obtained compounds, compound 4g has the best capability for detection of picric acid (PA), having good selectivity and high sensitivity. The detection of PA with 4g solution-coated paper strips at the picogram level is developed. A simple, portable, and low-cost method is provided for detecting PA in solution and contact mode.
Co-reporter:Jing Pei Huo;Guo Hua Deng;Wei Wu;Jin Feng Xiong;Ming Li Zhong;Zhao Yang Wang
Macromolecular Rapid Communications 2013 Volume 34( Issue 22) pp:1779-1784
Publication Date(Web):
DOI:10.1002/marc.201300637
Co-reporter:Ji Qi, Liangbin Huang, Zhaoyang Wang and Huanfeng Jiang  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 46) pp:8009-8013
Publication Date(Web):20 Aug 2013
DOI:10.1039/C3OB41590B
Ruthenium- and rhodium-catalyzed oxidative couplings between versatile directed aromatic C–H bonds and allylic alcohols have been achieved. This method provides efficient synthesis of functional β-aryl ketones and aldehydes in good to excellent yields, and the carbonyl group in the desired products was a significant synthon for organic synthesis.
Co-reporter:Jing-Pei Huo, Jian-Cheng Luo, Wei Wu, Jin-Feng Xiong, Guang-Zhen Mo, and Zhao-Yang Wang
Industrial & Engineering Chemistry Research 2013 Volume 52(Issue 34) pp:11850-11857
Publication Date(Web):July 29, 2013
DOI:10.1021/ie401149p
The multifunctional fluorescent brightening agents (FBAs) simultaneously possessing chiral 2(5H)-furanone and bis-1,2,3-triazole moieties are synthesized as designed via the Click reaction of N-[(5S)-5-menthoxy-2(5H)-furanonyl] amino acid propargyl esters with 4,4′-diazidostilbene-2,2′-disulfonate sodium salt tetrahydrate in high yields (over 90%). Their structures are systematically characterized. In addition, the testing results of their properties from fluorescence spectroscopy, photoisomerization, and ultraviolet (UV) protection factor (UPF) test show that the novel FBAs have excellent fastness to acid and light, as well as UV resistance. Especially, when a larger alkyl group in the side chain of amino acid moiety is introduced into the structure of the FBA, the designed compound has a better fluorescent brightening effect as anticipated. Moreover, in the experiments of its sorption on paper fibers, the scanning electron microscopy (SEM) images with it show a rough surface, while others without it show a relatively smooth surface.
Co-reporter:Jingpei Huo;Meixiang LÜ;Zhaoyang Wang;Yizhong Li
Chinese Journal of Chemistry 2012 Volume 30( Issue 10) pp:2411-2422
Publication Date(Web):
DOI:10.1002/cjoc.201200638

Abstract

A series of new chiral 2(5H)-furanone derivatives containing bis-1,2,3-triazole moiety were designed and synthesized from (5S)-5-alkoxy-3,4-dihalo-2(5H)-furanones 1, dicarboxyl amino acids 2, propargyl bromide, and organic azides 5 under mild conditions via the sequential three steps, including asymmetric Michael addition-elimination, substitution and no-ligand click reaction. Twelve new intermediates, including N-[5-alkoxy-2(5H)-furanonyl] dicarboxyl amino acids 3 and their corresponding propargyl esters 4, and twelve target molecules 6 were characterized by FTIR, 1H NMR, 13C NMR, MS and elemental analysis. The influences of different synthetic conditions and substrates in each step were investigated. The research provides a new method and idea for the synthesis of 2(5H)-furanone compounds with polyheterocyclic structure due to the diversities of four basic unit molecules.

Co-reporter:Ji Qi, Liangbin Huang, Zhaoyang Wang and Huanfeng Jiang
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 46) pp:NaN8013-8013
Publication Date(Web):2013/08/20
DOI:10.1039/C3OB41590B
Ruthenium- and rhodium-catalyzed oxidative couplings between versatile directed aromatic C–H bonds and allylic alcohols have been achieved. This method provides efficient synthesis of functional β-aryl ketones and aldehydes in good to excellent yields, and the carbonyl group in the desired products was a significant synthon for organic synthesis.
Cyanide
Tetradecane, 1-azido-
Benzoic acid, 3,4,5-tris(2-propyn-1-yloxy)-, methyl ester
3-Fluorobenzenesulfinic acid sodium salt
Benzoic acid, 3,4,5-tris(tetradecyloxy)-, methyl ester
Benzoic acid, 3,4,5-tris(octadecyloxy)-, methyl ester
1-(5-Methyl-1H-benzo[d]imidazol-2-yl)ethanamine
Benzoic acid, 3,4,5-tris(hexadecyloxy)-
Benzoic acid, 3,4,5-tris(tetradecyloxy)-