Publications by authors named "Haizhen Jiang"

20 Publications

  • Page 1 of 1

Glyphosate exposure attenuates testosterone synthesis via NR1D1 inhibition of StAR expression in mouse Leydig cells.

Sci Total Environ 2021 Sep 25;785:147323. Epub 2021 Apr 25.

Northwest A&F University, Yangling 712100, Shaanxi, China; Department of Clinical Veterinary Medicine, College of Veterinary Medicine, Northwest A&F University, Yangling 712100, Shaanxi, China; Key Laboratory of Animal Biotechnology of the Ministry of Agriculture, Northwest A&F University, Yangling 712100, Shaanxi, China. Electronic address:

Glyphosate is a broad-spectrum herbicide that impairs testosterone synthesis in mammals. Leydig cells (LCs), the primary producers of testosterone, demonstrate rhythmic expression of circadian clock genes both in vivo and in vitro. The nuclear receptor NR1D1 is an important clock component that constitutes the subsidiary transcriptional/translational loop in the circadian clock system. Nr1d1 deficiency resulted in diminished fertility in both male and female mice. However, whether NR1D1 is involved in the glyphosate-mediated inhibition of testosterone synthesis in LCs remains unclear. Here, the involvement of NR1D1 in glyphosate-mediated inhibition of testosterone synthesis was investigated both in vitro and in vivo. Glyphosate exposure of TM3 cells significantly increased Nr1d1 mRNA levels, but decreased Bmal1, Per2, StAR, Cyp11a1, and Cyp17a1 mRNA levels. Western blotting confirmed elevated NR1D1 and reduced StAR protein levels following glyphosate exposure. Glyphosate exposure also reduced testosterone production in TM3 cells. In primary LCs, glyphosate exposure also upregulated Nr1d1 mRNA levels and downregulated the mRNA levels of other clock genes (Bmal1 and Per2) and steroidogenic genes (StAR, Cyp17a1, Cyp11a1, and Hsd3b2), and inhibited testosterone synthesis. Moreover, glyphosate exposure significantly reduced the amplitude and shortened the period of PER2::LUCIFERASE oscillations in primary LCs isolated from mPer2 knock-in mice. Four weeks of oral glyphosate upregulated NR1D1 at both the mRNA and protein levels in mouse testes, and this was accompanied by a reduction in StAR expression. Notably, serum testosterone levels were also drastically reduced in mice treated with glyphosate. Moreover, dual-luciferase reporter and EMSA assays revealed that in TM3 cells NR1D1 inhibits the expression of StAR by binding to a canonical RORE element present within its promoter. Together, these data demonstrate that glyphosate perturbs testosterone synthesis via NR1D1 mediated inhibition of StAR expression in mouse LCs. These findings extend our understanding of how glyphosate impairs male fertility.
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http://dx.doi.org/10.1016/j.scitotenv.2021.147323DOI Listing
September 2021

Circadian clock gene BMAL1 controls testosterone production by regulating steroidogenesis-related gene transcription in goat Leydig cells.

J Cell Physiol 2021 Sep 17;236(9):6706-6725. Epub 2021 Feb 17.

Department of Clinical Veterinary Medicine, College of Veterinary Medicine, Northwest A&F University, Yangling, Shaanxi, China.

Testosterone is produced by Leydig cells (LCs) and undergoes diurnal changes in serum levels in rats, mice, and humans, but little is known in goats. The present study revealed that goat serum testosterone levels displayed diurnal rhythmic changes (peak time at ZT11.2). Immunohistochemical staining showed that BMAL1, a circadian clock protein, is highly expressed in goat LCs. ELISA revealed that both hCG (0-5 IU/ml) and 22R-OH-cholesterol (0-30 μM) addition stimulated testosterone synthesis in primary goat LCs in a dose-dependent manner. Treating goat LCs with hCG (5 IU/ml) significantly increased intracellular cAMP levels. Additionally, real-time quantitative polymerase chain reaction (PCR) analysis revealed that the circadian clock (BMAL1, PER1, PER2, DBP, and NR1D1) and steroidogenesis-related genes (SF1, NUR77, StAR, HSD3B2, CYP17A1, CYP11A1, and HSD17B3) showed rhythmic expression patterns in goat LCs following dexamethasone synchronization. Several Bmal1-Luc circadian oscillations were clearly observed in dexamethasone-treated goat LCs transfected with the pLV6-Bmal1-Luc plasmid. BMAL1 knockdown significantly downregulated mRNA levels of PER2, NR1D1, DBP, StAR, HSD3B2, SF1, NUR77, and GATA4, and dramatically decreased StAR and HSD3B2 protein levels and testosterone production. In contrast, BMAL1 overexpression significantly increased the mRNA and protein expression levels of StAR and HSD17B3 and enhanced testosterone production. Reporter assays revealed that goat BMAL1, or in combination with mouse CLOCK, activated goat HSD17B3 transcription in vitro. These data indicate that BMAL1 contributes to testosterone production by regulating transcription of steroidogenesis-related genes in goat LCs, providing a basis for further exploring the underlying mechanism by which the circadian clock regulates ruminant reproductive capability.
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http://dx.doi.org/10.1002/jcp.30334DOI Listing
September 2021

Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF-allyl bonds.

Org Biomol Chem 2021 03;19(9):2023-2029

Department of Chemistry, Shanghai University, Shanghai, 200444, PR China. and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, PR China.

An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.
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http://dx.doi.org/10.1039/d0ob02546aDOI Listing
March 2021

promotes prostaglandin E synthesis by upregulating transcription in response to increasing estradiol levels in pregnant mice.

Am J Physiol Endocrinol Metab 2021 04 8;320(4):E747-E759. Epub 2021 Feb 8.

Department of Clinical Veterinary Medicine, College of Veterinary Medicine, Northwest A&F University, Yangling, China.

Prostaglandin G/H synthase 2 (PTGS2) is a rate-limiting enzyme in prostaglandin synthesis. The present study assessed the role of the uterine circadian clock on transcription in response to steroid hormones during early pregnancy. We demonstrated that the core clock genes (, , , and ), , and and their encoded proteins, have rhythmic expression in the mouse uterus from to () of pregnancy. Progesterone (P) treatment of cultured uterus endometrial stromal cells (UESCs) isolated from reporter gene knock-in mice on D4 induced a phase shift in oscillations. This P-induced phase shift of oscillations was significantly attenuated by the P antagonist RU486. Additionally, the amplitude of oscillations was increased by estradiol (E) treatment in the presence of P. Consistently, the mRNA levels of clock genes ( and ), , and were markedly increased by E treatment of UESCs in the presence of P. Treatment with E also promoted prostaglandin E (PGE) synthesis by UESCs. Depletion of in UESCs by small-interfering RNA (siRNA) decreased the transcript levels of clock genes ( and ), , and compared with nonsilencing siRNA treatment. knockdown also inhibited PGE synthesis. Moreover, the mRNA expression levels of clock genes ( and ), , and , and their respective proteins were significantly decreased in the uterus of mice. Thus, these data suggest that in mice promotes PGE synthesis by upregulating in response to increases in E on D4 of pregnancy. Rhythmic expression of Bmal1 and Ptgs2 was observed in the uterus isolated from of pregnant mice. E increased the expression of Bmal1 and Ptg2 in UESCs isolated from mice on D4. The expression of Ptgs2 was significantly decreased in Bmal1-siRNA treated UESCs. knockdown also inhibited PGE synthesis. Thus, these data suggest that Bmal1 in mice promotes PGE synthesis by upregulating Ptgs2 in response to increases in E on D4 of pregnancy.
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http://dx.doi.org/10.1152/ajpendo.00466.2020DOI Listing
April 2021

Zearalenone perturbs the circadian clock and inhibits testosterone synthesis in mouse Leydig cells.

J Toxicol Environ Health A 2021 Feb 4;84(3):112-124. Epub 2020 Nov 4.

Department of Clinical Veterinary Medicine, College of Veterinary Medicine, Northwest A&F University , Yangling, China.

Zearalenone (ZEA), a mycotoxin, is known to impair reproductive capability by disrupting the synthesis and secretion of testosterone by Leydig cells (LCs), although the mechanism is unknown. Robust rhythmicity of circadian clock and steroidogenic genes were identified in LCs. The aim of this study was to examine whether ZEA significantly attenuated the transcription of core clock genes (, and ) as well as steroidogenic genes (, and ) in mouse testis Leydig cell line (TM3). Western blotting confirmed declines in BMAL1, NR1D1, and StAR protein levels. ZEA also suppressed secreted testosterone levels. In primary LCs, isolated from PER2::LUCIFERASE reporter gene knock in mice, ZEA diminished the amplitude of expression, and induced a phase shift and period extension. In primary LCs, ZEA also suppressed the expression levels of core clock and steroidogenic genes, reduced protein levels of BMAL1, and decreased testosterone secretion. expression of core clock and steroidogenic genes were reduced in testes of mice exposed to ZEA for 1 week leading to decreased serum testosterone levels. In summary, data suggest that ZEA may impair testosterone synthesis through attenuation of the circadian clock in LCs culminating in reproductive dysfunction in male mammals .
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http://dx.doi.org/10.1080/15287394.2020.1841699DOI Listing
February 2021

Degradation of Perfluorooctane Sulfonamide by Acinetobacter Sp. M and Its Extracellular Enzymes.

Chem Asian J 2019 Aug 16;14(16):2780-2784. Epub 2019 Jul 16.

Department of Biology, University of Waterloo, 200 University Avenue West, Waterloo, Ontario, N2L 3G1, Canada.

The Acinetobacter sp. strain M isolated from a contaminated soil sample in Jiangsu Province of China was found to be able to degrade perfluorooctane sulfonamide (PFOSA) effectively. Fluoride anion (F ) released from PFOSA degradation was detected by ion chromatography, and showed positive correlation to the growth curve of Acinetobacter sp. strain M. The PFOSA degradation efficiency of strain M was approximately 27 %, as assessed by GC analysis. It was shown that enzymes localized outside of cells of Acinetobacter sp. strain M catalyzed the degradation of PFOSA. This further indicates a possibly new (multi-step/pathway) mechanism for PFOSA degradation. It revealed that the extracellular enzyme of the Acinetobacter strain M preferentially cleaves carbon-carbon and carbon-fluorine bonds instead of destroying the carbon-sulfur bond. The growth condition for Acinetobacter sp. strain M was optimized at 30 °C and pH 7.0 in the presence of 2000 mg L of PFOSA and 0.5 % (v/v) of Tween-20. The optimal PFOSA degradation time was found to be 12 h, with a degradation efficiency of 76 % by extracellular enzymes in strain M as determined by GC analysis. The result may provide potential applications for biodegradition of perfluoro organic compounds, such as derivatives of perfluorooctane (C8).
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http://dx.doi.org/10.1002/asia.201900638DOI Listing
August 2019

Cholesteryl Liquid Crystals as Oil-Based Lubricant Additives: Effect of Mesogenic Phases and Structures on Tribological Characteristics.

Langmuir 2019 May 15;35(21):6981-6992. Epub 2019 May 15.

Laboratory for Advanced Lubricating Materials , Shanghai Advanced Research Institute, Chinese Academy of Sciences , Shanghai 201210 , China.

Mechanical operation could be seriously affected by friction and controlling it by oil lubrication has been considered as an effective way. Good lubricant additives are very necessary to avoid the friction damages, and to find or design new additives is always a challenge. In this study, a systematic investigation of using cholesteryl liquid crystals (LCs) as lubricant additives to obtain exceptional tribological behaviors was performed. In total, four cholesteryl LC compounds were synthesized targetedly and their thermal and mesogenic properties were studied to see the inherent relationship between the mesogenic phases and antifriction and antiwear performance. Through a series of tribological and related tests, including the UMT TriboLab test, three-dimensional optical microscopy, oil film thickness and viscosity tests, etc., the effect of the mesogenic phases and structures of the synthesized cholesteryl LCs on their tribological properties as lubricant additives was investigated and a related mechanism was analyzed. The result showed that within and close to the mesogenic phase temperature ranges, which we called as effective temperature ranges of LC additives ( T), the LCs presented better tribological behaviors, meaning they could be used in special lubrication applications that need to be confined in certain temperature scopes; however, the ester groups with long alky tails could help dissolve in base oils and adsorb onto the friction pairs. Among the four LCs, LC-D with a long perfluoroalkyl tail brought widest mesogenic phase with considerably enhanced lubrication performance and increased oil film thickness, viscosity, and thermal stability, indicating that the perfluoroalkyl group could be well used in the structural modification of LC additives to give unexpected tribological performance. This study, in conjunction with our experimental data, suggested that the liquid crystals may be evaluated as potential friction modifiers for temperature-controllable lubrication and also shed a fresh light on the development of novel liquid crystal lubrication materials.
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http://dx.doi.org/10.1021/acs.langmuir.9b00459DOI Listing
May 2019

MRI reveals slow clearance of dead cell transplants in mouse forelimb muscles.

Mol Med Rep 2017 Oct 27;16(4):4068-4074. Epub 2017 Jul 27.

CAS Key Laboratory of Nano‑Bio Interface and Division of Nanobionics Research, Suzhou Institute of Nano‑Tech and Nano‑Bionics, Chinese Academy of Sciences, Suzhou, Jiangsu 215123, P.R. China.

A small molecule tetraazacyclododecane-1,4,7,10-tetraacetic acid (Gd‑DOTA)4‑TPP agent is used to label human mesenchymal stem cells (hMSCs) via electroporation (EP). The present study assessed the cytotoxicity of cell labeling, in addition to its effect on cell differentiation potential. There were no significant adverse effects on cell viability or differentiation induced by either EP or cellular uptake of (Gd‑DOTA)4‑TPP. Labeled live and dead hMSCs were transplanted into mouse forelimb muscles. T2‑weighted magnetic resonance imaging (MRI) was used to track the in vivo fate of the cell transplants. The labeling and imaging strategy allowed long term tracking of the cell transplants and unambiguous distinguishing of the cell transplants from their surrounding tissues. Cell migration was observed for live hMSCs injected into subcutaneous tissues, however not for either live or dead hMSCS injected into limb muscles. A slow clearance process occurred of the dead cell transplants in the limb muscular tissue. The MRI results therefore reveal that the fate and physiological activities of cell transplants depend on the nature of their host tissue.
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http://dx.doi.org/10.3892/mmr.2017.7100DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5646989PMC
October 2017

Ag(i)-Catalyzed oxidative decarboxylation of difluoroacetates with activated alkenes to form difluorooxindoles.

Org Biomol Chem 2017 Jun;15(25):5308-5317

Department of Chemistry, Innovative Drug Research Center, Shanghai University, China.

A silver-catalyzed oxidative decarboxylative gem-difluoromethylenation of difluoroacetates with activated alkenes under mild reaction conditions has been developed. This radical cascade reaction provides a new method for the construction of a variety of gem-difluoromethylenated oxindoles.
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http://dx.doi.org/10.1039/c7ob00955kDOI Listing
June 2017

Ag-Initiated gem-Difluoromethylenation of the Nitrogen Center of Arenediazonium Salts to gem-Difluoromethylene Azo Compounds.

Org Lett 2017 05 21;19(9):2406-2409. Epub 2017 Apr 21.

Department of Chemistry, Innovative Drug Research Center, Shanghai University , Shanghai, 200444, P. R. China.

An efficient method for the synthesis of the thermally stable and pharmaceutically important gem-difluoromethylene azo compounds is developed. This protocol achieved gem-difluoromethylenation of the nitrogen center of arenediazonium salts through in situ generated benzo-1,3-diazolic difluoromethylene radical addition to arenediazonium salts under mild Ag-initiated conditions.
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http://dx.doi.org/10.1021/acs.orglett.7b00936DOI Listing
May 2017

Silver-catalyzed oxidative decarboxylation of difluoroacetates: efficient access to C-CF2 bond formation.

Chem Commun (Camb) 2016 Jan 11;52(8):1598-601. Epub 2015 Dec 11.

Department of Chemistry, School of Material Science and Engineering, Innovative Drug Research Center, Shanghai University, China.

A mild, versatile and efficient method for the silver(I)-catalyzed oxidative decarboxylative gem-difluoromethylenation has been developed. The radical cascade reaction comprises the addition of an oxidatively generated difluoromethylene radical to the isonitrile functionality and subsequent homolytic aromatic substitution. It provides a novel and efficient access to the C-CF2 bond formation.
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http://dx.doi.org/10.1039/c5cc09179aDOI Listing
January 2016

Direct gem-difluoromethylenation of sp(3)-hybridized carbon center through copper-mediated radical/radical cross-coupling for the construction of a CH2-CF2 linkage.

Chem Commun (Camb) 2015 Nov;51(87):15756-9

Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. China. and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China.

Efficient direct gem-difluoromethylenation of an sp(3)-hybridized carbon center in benzyl bromides using benzo-1,3-azolic (oxa-, thia- or aza-) difluoromethyl bromides for construction of a CH2-CF2 linkage has been developed through radical/radical C-C cross-coupling via two separate single electron transfer processes (SET) under the promotion of different copper sources.
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http://dx.doi.org/10.1039/c5cc05677bDOI Listing
November 2015

An efficient regioselective hydrodifluoromethylation of unactivated alkenes with TMSCF₂CO₂Et at ambient temperature.

Chem Commun (Camb) 2014 Sep;50(68):9749-52

Department of Chemistry, School of Materials Science and Engineering, Shanghai University, Shanghai 200444, China.

A mild, versatile and efficient method for the regioselective hydrodifluoromethylation of unactivated alkenes has been developed. This Ag-mediated Csp(3)-CF2 bond forming reaction provides easy access to a variety of vicinal α-difluoroacetate-containing alkanes.
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http://dx.doi.org/10.1039/c4cc04591bDOI Listing
September 2014

Enhancement of neighbouring-group participation in Cu0-promoted cross-coupling gem-difluoromethylenation of aryl/alkenyl halides with 1,3-azolic difluoromethyl bromides.

Chemistry 2014 Aug 2;20(32):10084-92. Epub 2014 Jul 2.

Department of Chemistry, Shanghai University, Shanghai, 200444 (P.R. China); Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 (P.R. China).

A copper(0)-promoted direct reductive gem-difluoromethylenation of unactivated aryl or alkenyl halides with benzo-1,3-azolic (oxa-, thia- or aza-) difluoromethyl bromides or 2-bromodifluoromethyl-1,3-oxazoline has been developed for the construction of pharmaceutically important gem-difluoromethylene-linked twin molecules. The unique π-conjugated aryl-fused 1,3-azolic moiety in difluoromethyl bromide substrates could stabilise the reaction intermediates, which promotes the reactivities, providing facile access to the cross-coupling products in good to excellent yields, and allowing significant functional group tolerance. The reaction exhibits an enhanced neighbouring-group-participation effect. This method could provide a new strategy for the construction of gem-difluoromethylene-linked identical or nonidentical twin drugs through further functionalisation of 1,3-azolic skeletons.
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http://dx.doi.org/10.1002/chem.201402205DOI Listing
August 2014

Highly effective copper-mediated gem-difluoromethylenation of arylboronic acids.

Chem Commun (Camb) 2014 Jul;50(56):7527-30

School of Materials Science and Engineering, Department of Chemistry, Shanghai University, Shanghai 200444, China.

A copper-mediated gem-difluoromethylenation of aryl, heteroaryl and vinyl boronic acids with bromodifluoromethylated oxazole or thiazole derivatives has been developed. This novel reaction showed an excellent functional group tolerance and wide substrate scope, providing facile access to practical application in drug discovery and development.
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http://dx.doi.org/10.1039/c4cc03321cDOI Listing
July 2014

Room-temperature Cu(II)-catalyzed aromatic C-H azidation for the synthesis of ortho-azido anilines with excellent regioselectivity.

Chem Commun (Camb) 2014 Jun 22;50(43):5733-6. Epub 2014 Apr 22.

Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai, China.

Cu(ii)-catalyzed aromatic C-H azidation with azido-benziodoxolone under mild conditions has been described. The primary amine exhibits an excellent ortho-directing effect, providing ortho-azidated anilines as the sole products.
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http://dx.doi.org/10.1039/c4cc01481bDOI Listing
June 2014

A facile total synthesis of drospirenone isomers containing 14β-hydrogen configuration.

Org Biomol Chem 2013 Oct 29;11(38):6597-603. Epub 2013 Aug 29.

Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China.

A facile strategy for the preparation of two isomeric drospirenones 13 and 16 possessing a 14β-hydrogen was developed, using 3β-hydroxyandrost-5-en-17-one as the starting material. The total synthetic route involves eight steps, giving 2% overall yield. The structures of the main compounds 11, 13, 14 and 16 were determined by single crystal XRD analysis.
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http://dx.doi.org/10.1039/c3ob41211cDOI Listing
October 2013

Nucleophile-dependent regioselective reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazolines.

J Org Chem 2013 May 19;78(9):4261-9. Epub 2013 Apr 19.

Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, People's Republic of China.

Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (S(RN)1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the C═N bond.
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http://dx.doi.org/10.1021/jo400073dDOI Listing
May 2013

C-9 fluorenyl substituted anthracenes: a promising new family of blue luminescent materials.

Org Lett 2010 Sep;12(17):3874-7

Department of Chemistry, Shanghai University, Shanghai, China.

Syntheses, optical, and electrochemical properties of novel C-9 fluorenyl substituted anthracenes linked by a tetrahedral sp(3)-hybridized carbon atom are reported for blue light emitting materials. Remarkably, an unoptimized organic light-emitting diode based on 1-fold fluorene-functionalized anthracene 3 exhibits a radiance of 4100 cd/m(2) at 12 V and a maximum EL efficiency of 1.36 cd/A with color purity CIE x, y (0.157, 0.082), which is very close to the National Television System Committee standard blue.
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http://dx.doi.org/10.1021/ol101553aDOI Listing
September 2010

One-pot cyclization of 2-aminophenethyl alcohols: a novel and direct approach to the synthesis of N-acyl indolines.

J Org Chem 2007 Nov 1;72(24):9364-7. Epub 2007 Nov 1.

Department of Chemistry, Shanghai University, Shanghai, China.

A unique one-pot cyclization of 2-aminophenethyl alcohols with carboxylic acids in the presence of PPh3, CCl4, and NEt3 furnished the formation of N-acyl indolines in good to excellent yields. This new approach provides an efficient, scalable, low-cost, and direct access to the biologically important indolines which are further oxidizable to indoles and oxindoles.
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http://dx.doi.org/10.1021/jo701566vDOI Listing
November 2007