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Dive into the research topics where Lijuan Jiao is active.

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Featured researches published by Lijuan Jiao.


Journal of Organic Chemistry | 2011

Regioselective stepwise bromination of boron dipyrromethene (BODIPY) dyes.

Lijuan Jiao; Weidong Pang; Jinyuan Zhou; Yun Wei; Xiaolong Mu; Guifeng Bai; Erhong Hao

Halogenated BODIPYs are important synthetic precursors and potential sensitizers for photodynamic therapy (PDT). Electrophilic bromination of pyrrolic-unsubstituted BODIPYs using bromine regioselectively generated mono- to heptabromoBODIPYs in a stepwise fashion in good to excellent yields. These resultant bromoBODIPYs were applied for regioselective substitution and Suzuki coupling reaction to generate BODIPYs 4, 5, 6, and 7 in good to excellent yields. According to NMR and X-ray analysis results, the stepwise bromination first takes place at 2,6-, then at 3,5-, and eventually at 1,7-positions, whereas the regioselective substitution occurs first at 3,5- then at 1,7-positions of the chromophore. The spectroscopic properties of these resultant BODIPYs were studied, which shows the potential application of these bromoBODIPYs as sensitizers for PDT.


Journal of Organic Chemistry | 2009

β-Formyl-BODIPYs from the Vilsmeier−Haack Reaction

Lijuan Jiao; Changjiang Yu; Jilong Li; Zhaoyun Wang; Min Wu; Erhong Hao

A series of beta-formyl-BODIPYs 2 were synthesized in high yields from tetramethyl-BODIPYs 1 via the Vilsmeier-Haack reaction and were further functionalized using a Knoevenagel condensation to generate novel BODIPYs 3 and 4.


Journal of Organic Chemistry | 2010

Synthesis and Functionalization of Asymmetrical Benzo-Fused BODIPY Dyes

Lijuan Jiao; Changjiang Yu; Mingming Liu; Yangchun Wu; Kebing Cong; Ting Meng; Yuqing Wang; Erhong Hao

A series of asymmetrical benzo-fused BODIPY dyes were synthesized from the Sonogashira coupling and nucleophilic substitution reactions on the 3-halogenated benzo-fused BODIPY, generated from readily available 3-halogeno-1-formylisoindoles in a two-step synthetic procedure. This novel BODIPY platform provides an easy path for the linking of BODIPY fluorophore to various desired functionalities as demonstrated in this work. Most of the resulting BODIPY dyes show long-wavelength absorption and fluorescence emission, with good fluorescence quantum yields and long fluorescence lifetimes.


New Journal of Chemistry | 2009

A selective fluorescent sensor for imaging Cu2+ in living cells

Lijuan Jiao; Jilong Li; Shengzhou Zhang; Chao Wei; Erhong Hao; M. Graça H. Vicente

Copper ion is a biochemically essential yet toxic metal ion, connected to serious neurodegenerative diseases, and also has been identified as an environmental pollutant. For the effective detection of Cu2+ in biological and environmental systems, we have developed a new membrane-permeable Cu2+-selective water-soluble BODIPY 1, which was synthesized by nucleophilic disubstitution of novel 3,5-diiodo-BODIPY 4 with N,N-bis(2-hydroxyethyl)amines. BODIPY 1 shows a highly sensitive and selective fluorescence response to Cu2+ in aqueous solution. Fluorescence image experiments establish that 1 can be used to monitor intracellular Cu2+ within living cells.


Organic and Biomolecular Chemistry | 2010

Long wavelength red fluorescent dyes from 3,5-diiodo-BODIPYs

Lijuan Jiao; Changjiang Yu; Timsy Uppal; Mingming Liu; Yan Li; Yunyou Zhou; Erhong Hao; Xiaoke Hu; M. Graça H. Vicente

Amphiphilic and long wavelength red fluorescent dyes (4 and 7) were prepared from the Sonogashira coupling reactions of 3,5-diiodo-BODIPYs (1 and 6). One of these compounds, BODIPY 7, readily accumulated within human carcinoma HEp2 cells and was found to localize mainly within the endoplasmic reticulum (ER).


Organic Letters | 2014

Highly Fluorescent BF2 Complexes of Hydrazine–Schiff Base Linked Bispyrrole

Changjiang Yu; Lijuan Jiao; Ping Zhang; Zeya Feng; Chi Cheng; Yun Wei; Xiaolong Mu; Erhong Hao

A series of BF2 complexes of hydrazine-Schiff base linked bispyrrole have been prepared from a simple two-step reaction from commercially available substances and are highly fluorescent in solution, film, and solid states with larger Stokes shift and excellent photostabilities comparable or even super to those of their BODIPY analogues. These resultant fluorescent dyes are highly susceptible to the postfunctionalization, as demonstrated in this work via the Knoevenagel condensation to introducing functionalities or tether groups to the chromophore.


Organic Letters | 2014

β-Thiophene-Fused BF2-Azadipyrromethenes as Near-Infrared Dyes

Yayang Wu; Chi Cheng; Lijuan Jiao; Changjiang Yu; Sufan Wang; Yun Wei; Xiaolong Mu; Erhong Hao

A facile synthetic route to a new class of near-IR β-thiophene-fused BF2-azadipyrromethenes (aza-BDTPs) is presented. Sharp absorption and fluorescence emission bands at around 800 nm were observed for these highly photostable aza-BDTPs, with a large absorption coefficient and very low absorptions in the visible range from 700 to 380 nm.


Journal of Organic Chemistry | 2014

Accessing near-infrared-absorbing BF2-azadipyrromethenes via a push-pull effect.

Lijuan Jiao; Yayang Wu; Sufan Wang; Xiaoke Hu; Ping Zhang; Changjiang Yu; Kebing Cong; Qianli Meng; Erhong Hao; M. Graça H. Vicente

Novel aza-BODIPYs with significant bathochromic shifts were designed and synthesized by installation of strong electron-withdrawing groups on the para-positions of 1,7-phenyls and electron-donating groups on the para-positions of 3,4-phenyls. These dyes show strong NIR fluorescence emissions up to 756 nm, and absorptions up to 720 nm.


Organic Letters | 2015

Diversity-Oriented Facile Access to Highly Fluorescent Membrane-Permeable Benz[c,d]indole N-Heteroarene BF2 Dyes

Chi Cheng; Naixun Gao; Changjiang Yu; Zhaoyun Wang; Jun Wang; Erhong Hao; Yun Wei; Xiaolong Mu; Yanli Tian; Chongzhao Ran; Lijuan Jiao

A diversity-oriented one-pot synthesis of a series of membrane-permeable BF2-rigidified benz[c,d]indole N-heteroarene BBN and BBC dyes has been achieved from the condensation of two commercial components (benz[c,d]indol-2-one and a set of N-heteroarene derivatives that can be selected from thousands of commercially available sources) and the subsequent in situ BF2 complexation reaction. These dyes enjoy a set of excellent photophysical properties including the large Stokes shift, high solution and solid-state fluorescence, and excellent photostabilities.


Organic and Biomolecular Chemistry | 2012

Synthesis of pyrrolyldipyrrinato BF2 complexes by oxidative nucleophilic substitution of boron dipyrromethene with pyrrole

Min Zhang; Erhong Hao; Jinyuan Zhou; Changjiang Yu; Guifeng Bai; Fengyun Wang; Lijuan Jiao

Direct oxidative nucleophilic substitution of the 3-hydrogen of BODIPY dyes by pyrrole has been developed under reflux condition under oxygen, from which a series of pyrrolyldipyrrinato BF(2) complexes 1a-h, as extended BODIPYs, have been synthesized. Most of these BODIPYs show strong fluorescence emissions at wavelengths over 600 nm in six solvents of different polarity. Removal of the BF(2) group from BODIPY 1e gave the corresponding free base pyrrolyldipyrrin 7 as an analog of the natural product prodigiosin, in high yield.

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Erhong Hao

Anhui Normal University

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Yun Wei

Anhui Normal University

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Xiaolong Mu

Anhui Normal University

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Qinghua Wu

Anhui Normal University

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Jun Wang

Anhui Normal University

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Wanle Sheng

Anhui Normal University

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Zhaoyun Wang

Anhui Normal University

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Yangchun Wu

Anhui Normal University

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Jinyuan Zhou

Anhui Normal University

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