Ju-Li Jiang - Cochemist

Acid/base-controllable fluorescent molecular switches based on cryptands and basic N-heteroaromatics

Co-reporter:Ming Cheng;Jing Zhang;Xintong Ren;Shuwen Guo;Tangxin Xiao;Xiao-Yu Hu;Juli Jiang;Leyong Wang

Chemical Communications 2017 vol. 53(Issue 86) pp:11838-11841

Publication Date(Web):2017/10/26

DOI:10.1039/C7CC07469G

Two kinds of fluorescent BMP32C10-based cryptands 1 and 2 have been developed. Cryptand 1 contains a binaphthol group, while cryptand 2 bears a coumarin group in their third arms. Based on this design, novel self-assemblies constructed from cryptand 1 or 2 and basic N-heteroaromatic guests 3–6 were successfully obtained. Moreover, the threading/dethreading processes of the host–guest complexes could be well switched by the alternate addition of acid/base, and accompanied by concurrent changes in fluorescence.

Supramolecular polymers based on a pillar[5]arene-fused cryptand: design, fabrication and degradation accompanied by a fluorescence change

Co-reporter:Qi Wang;Ming Cheng;Lu Tian;Quli Fan;Juli Jiang

Polymer Chemistry (2010-Present) 2017 vol. 8(Issue 39) pp:6058-6063

Publication Date(Web):2017/10/10

DOI:10.1039/C7PY01096F

Novel linear supramolecular polymers based on a pillar[5]arene-fused cryptand have been constructed easily and conveniently, in which three orthogonal interactions: quadruple hydrogen bonding, cryptand-based host–guest recognition, and pillar[5]arene-based host–guest interaction were combined together. Furthermore, the resulting linear supramolecular polymers can be effectively depolymerized accompanying a fluorescence change by the addition of another competitive cryptand host.

Modulating the properties of quadruple hydrogen bonded supramolecular polymers by photo-cross-linking between the coumarin moieties

Co-reporter:Qi Wang, Ming Cheng, Ju-Li Jiang, Le-Yong Wang

Chinese Chemical Letters 2017 Volume 28, Issue 4(Volume 28, Issue 4) pp:

Publication Date(Web):1 April 2017

DOI:10.1016/j.cclet.2017.02.008

Novel linear supramolecular polymers were successfully constructed by self-assemblies of coumarin-bridged bifunctional UPy derivative. Benefitting from the photodimerization ability of the coumarin moieties, the linear supramolecular polymers could form the large three-dimensional polymer networks upon UV light irradiation via photo-cross-linking, which provides a viable and alternative procedure to modulate the properties of supramolecular polymers.Download high-res image (103KB)Download full-size image

4-Methylcoumarin-bridged fluorescent responsive cryptand: from [2+2] photodimerization to supramolecular polymer

Co-reporter:Ming Cheng, Chenhao Yao, Yihan Cao, Qi Wang, Yi Pan, Juli Jiang and Leyong Wang

Chemical Communications 2016 vol. 52(Issue 56) pp:8715-8718

Publication Date(Web):06 Jun 2016

DOI:10.1039/C6CC03624D

A fluorescent responsive BMP32C10-based cryptand host was successfully synthesized by introducing a 4-methylcoumarin group to the third arm of the cryptand. The cryptand was able to undergo [2+2] photodimerization on UV irradiation (λ = 365 nm) and, based on the photodimerization and host–guest interaction, a new supramolecular polymer was constructed in a convenient manner.

A Phosphine Oxide Functional Group Based [2]Rotaxane That Operates as a Multistable Molecular Shuttle

Co-reporter:Ming Cheng;Dr. Li Liu;Yihan Cao; Juli Jiang; Leyong Wang

ChemPhysChem 2016 Volume 17( Issue 12) pp:1835-1839

Publication Date(Web):

DOI:10.1002/cphc.201501016

Abstract

A switchable [2]rotaxane based on a pyridinediamide crown ether macrocycle and a thread bearing phosphine oxide, urea, and dibenzylammonium functional groups was successfully developed and characterized by ¹H NMR and 2D NMR spectroscopy, mass spectrometry, and single-crystal analysis. The three recognition sites in the [2]rotaxane were sorted from strong to weak, according to their bonding abilities, so that the macrocycle could move along the thread from one side to the other in a directional way, operating as a multistable molecular shuttle.

A pillar[5]arene-fused cryptand: from orthogonal self-assembly to supramolecular polymer

Co-reporter:Qi Wang, Ming Cheng, Yue Zhao, Lin Wu, Juli Jiang, Leyong Wang and Yi Pan

Chemical Communications 2015 vol. 51(Issue 17) pp:3623-3626

Publication Date(Web):23 Jan 2015

DOI:10.1039/C5CC00130G

A pillar[5]arene-fused cryptand with two different cavities was synthesized successfully. It was found that the novel tricyclic host could associate with two different guest species in an orthogonal manner. And based on this orthogonal self-assembly of two host–guest interactions, a novel type of supramolecular polymer was constructed easily and conveniently.

PO functional group-containing cryptands: from supramolecular complexes to poly[2]pseudorotaxanes

Co-reporter:Qi Wang, Ming Cheng, Shuhan Xiong, Xiao-Yu Hu, Juli Jiang, Leyong Wang and Yi Pan

Chemical Communications 2015 vol. 51(Issue 13) pp:2667-2670

Publication Date(Web):22 Dec 2014

DOI:10.1039/C4CC09487E

Two types of cryptand-based host–guest complexes were constructed successfully, in which PO functional groups were located at the different positions of the third arms. Consequently, supramolecular poly[2]pseudorotaxanes with almost linear and zigzag shapes were formed in the solid state.

A Ferrocene-Functionalized Bistable [2]Rotaxane with Switchable Fluorescence

Co-reporter:Li Liu;Qi Wang;Ming Cheng;Dr. Xiao-Yu Hu;Dr. Juli Jiang;Dr. Leyong Wang

Asian Journal of Organic Chemistry 2015 Volume 4( Issue 3) pp:221-225

Publication Date(Web):

DOI:10.1002/ajoc.201402155

Abstract

A switchable, bistable molecular shuttle based on dialkylammonium ion and urea functional recognition sites, and a macrocycle bearing a ferrocenyl unit has been constructed, in which the ferrocenyl macrocycle can be easily switched along the thread by addition of acid/base or by addition/removal of acetate anions. The shuttling motion of the macrocycle is accompanied with different fluorescence responses via the adjustment of the photoinduced electron transfer (PET) effect between the ferrocene electron donor and the fluorophores.

A switchable bistable [2]rotaxane based on phosphine oxide functional group

Co-reporter:Shuang-Jin Zhang, Qi Wang, Ming Cheng, Xiao-Hong Qian, Yang Yang, Ju-Li Jiang, Le-Yong Wang

Chinese Chemical Letters 2015 Volume 26(Issue 7) pp:885-888

Publication Date(Web):July 2015

DOI:10.1016/j.cclet.2015.05.015

A switchable bistable rotaxane based phosphine oxide functional group-containing macrocycle has been constructed successfully, in which the macrocycle can be easily switched between dibenzylammonium and triazole recognition sites by using the simple base/acid stimuli.A switchable bistable rotaxane based phosphine oxide functional group-containing macrocycle has been constructed successfully, in which the macrocycle can be easily switched between dibenzylammonium and triazole recognition sites by using the simple base/acid stimuli.

Redox-switchable host–guest systems based on a bisthiotetrathiafulvalene-bridged cryptand

Co-reporter:Qi Wang, Ming Cheng, Yue Zhao, Zhen Yang, Juli Jiang, Leyong Wang and Yi Pan

Chemical Communications 2014 vol. 50(Issue 98) pp:15585-15588

Publication Date(Web):27 Oct 2014

DOI:10.1039/C4CC07770A

By attaching a bisthiotetrathiafulvalene (STTFS) unit to the third arm of the cryptand, a redox-switchable bis(m-phenylene)-32-crown-10-based cryptand was synthesized successfully. It was found that the dethreading–rethreading processes between this cryptand and the guests could be well-controlled in different redox states owing to the specific redox-active properties of the STTFS unit.

The self-complexation of mono-urea-functionalized pillar[5]arenes with abnormal urea behaviors

Co-reporter:Mengfei Ni, Xiao-Yu Hu, Juli Jiang and Leyong Wang

Chemical Communications 2014 vol. 50(Issue 11) pp:1317-1319

Publication Date(Web):08 Nov 2013

DOI:10.1039/C3CC47823H

Mono-urea-functionalized pillar[5]arenes were prepared which exhibited abnormal urea behaviors. They were shown to form pseudo[1]rotaxanes with poor anion binding abilities in solution and [c2]daisy chains with an abnormal urea motif in the solid state.

Squaramide-based tripodal receptors for selective recognition of sulfate anion

Co-reporter:Can Jin, Man Zhang, Lin Wu, Yangfan Guan, Yi Pan, Juli Jiang, Chen Lin and Leyong Wang

Chemical Communications 2013 vol. 49(Issue 20) pp:2025-2027

Publication Date(Web):24 Jan 2013

DOI:10.1039/C3CC00196B

Squaramide-based tripodal anion receptors 1–3 have been prepared and their anion binding properties with various inorganic anions were investigated. Receptor 1 formed a dimeric complex in solid state and a 1:1 complex in solution with SO42−. All receptors 1–3 could selectively encapsulate SO42−via hydrogen bonds over other examined anions.

Cu-Catalyzed Cross-Dehydrogenative Coupling Reactions of (Benzo)thiazoles with Cyclic Ethers

Co-reporter:Zengyang Xie, Yuping Cai, Hongwen Hu, Chen Lin, Juli Jiang, Zhaoxu Chen, Leyong Wang, and Yi Pan

Organic Letters 2013 Volume 15(Issue 17) pp:4600-4603

Publication Date(Web):August 22, 2013

DOI:10.1021/ol4022113

Copper-catalyzed cross-dehydrogenative coupling (CDC) reactions of (benzo)thiazoles with cyclic ethers were developed under mild conditions. In particular, the formation of C–C bonds via the CDC reactions between non-benzo-fused azoles and ethers are reported for the first time. In addition, the acetals, known as the masked 2-thiazolecarboxaldehydes, could be successfully obtained by this CDC reaction. The preliminary mechanism and supportive DFT calculations are discussed as well.

Cu-catalyzed direct C–H bond functionalization: a regioselective protocol to 5-aryl thiazolo[3,2-b]-1,2,4-triazoles

Co-reporter:Zengyang Xie, Xiaojun Zhu, Yangfan Guan, Dunru Zhu, Hongwen Hu, Chen Lin, Yi Pan, Juli Jiang and Leyong Wang

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 8) pp:1390-1398

Publication Date(Web):12 Dec 2012

DOI:10.1039/C2OB27326H

An efficient, regioselective C-5 arylation of thiazolo[3,2-b]-1,2,4-triazoles catalyzed by a simple copper catalyst was developed. This arylation proceeded smoothly and tolerated a variety of functional groups (44 examples). A wide range of functionalized thiazolo[3,2-b]-1,2,4-triazole derivatives were obtained in high yields (up to 99% yield). Possible catalytic cycles of the arylation were also discussed.

Synthesis, chemo-selective properties of substituted 9-aryl-9H-fluorenes from triarylcarbinols and enantiomerical kinetics of chiral 9-methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene

Co-reporter:Ming-yu Teng, Ying Liu, Shao-lu Li, Guoli Huang, Juli Jiang and Leyong Wang

RSC Advances 2013 vol. 3(Issue 23) pp:9016-9022

Publication Date(Web):08 Apr 2013

DOI:10.1039/C3RA41273C

9-Aryl-fluorenes were synthesized conveniently from triarylcarbinols in the presence of TsOH. Notably, the orientation of the intramolecular aromatic substitution reaction was dictated by the nature of the substituents on the aryl rings of triarylcarbinols, owing to electronic and conjugated effects. In particular, triarylcarbinols with (3-methoxy)phenyl and naphthalenyl groups formed benzo[a]fluorenes selectively. Moreover, 9-methoxy-11-(naphthalen-1-yl)-11H-benzo[a] fluorene (2g), with a center of chirality, exists as a mixture of diastereoisomers, due to the restricted rotation of a C–C single bond. First-order rate constants for the enantiomerization of 2g in DMSO were obtained over the temperature from 297 K to 393 K, and thermodynamic parameters were determined as ΔH‡ = 99.7 kJ mol−1, ΔS‡373 K = 37.7 J mol−1 K−1, and ΔG‡373 K = 85.6 kJ mol−1 by Eyring plot analysis.

Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes

Co-reporter:Can Jin, Man Zhang, Chao Deng, Yangfan Guan, Jun Gong, Dunru Zhu, Yi Pan, Juli Jiang, Leyong Wang

Tetrahedron Letters 2013 Volume 54(Issue 8) pp:796-801

Publication Date(Web):20 February 2013

DOI:10.1016/j.tetlet.2012.11.117

Novel calix[4]arene-based anion receptors 1–3 with bis-squaramide moieties were designed and synthesized. Their sensing properties with various anions were investigated by UV–vis, ESI-MS, and 1H NMR spectra. The experimental results revealed that there were two types of interaction modes where receptor 1 bound biologically important H2PO4−, F−, and AcO− ions selectively over other anions in the hydrogen bonding interaction mode, while receptors 2 and 3 displayed deprotonation behavior with basic anions (F−, AcO−, and H2PO4−) via acid–base interaction mode. Receptors 2 and 3 were proved to be efficient ‘naked-eye’ sensors for F− and AcO− with marked color changes.

Ligand-Free Copper-Catalyzed Regioselective C-2 Arylation of Imidazo[2,1-b]thiazoles

Co-reporter:Guoli Huang, Hongsheng Sun, Xiaojie Qiu, Can Jin, Chen Lin, Yingzhong Shen, Juli Jiang, and Leyong Wang

Organic Letters 2011 Volume 13(Issue 19) pp:5224-5227

Publication Date(Web):September 13, 2011

DOI:10.1021/ol2021109

An effective, regioselective C-2 arylation of imidazo[2,1-b]thiazoles catalyzed by Cu(I) has been developed. This arylation proceeded smoothly without promotion of the ligands, and various functional (22 samples) groups were well tolerated. Preliminary mechanistic studies of this arylation are also reported.

Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction

Co-reporter:Hui Wu;Can Jin;GuoLi Huang;LianJun Wang;JuLi Jiang

Science China Chemistry 2011 Volume 54( Issue 6) pp:951-956

Publication Date(Web):2011 June

DOI:10.1007/s11426-011-4272-4

Two new bis-imidazolinium salts (4a, 4b) have been synthesized as precursors of N-heterocyclic carbenes (NHCs) from the commercially available (R)-2,2′-dihydroxy-1,1′-binaphthalene. The two bis-imidazolinium salts were used as efficient precursor of NHC ancillary ligands in the palladium-catalyzed Heck reaction. Good to excellent yields and high stereoselectivities were obtained with ethyl acrylate, acrylonitrile, and acrylamide as starting materials. The structure of bis-imidazolinium salt 4b was further characterized by single crystal X-ray diffraction analysis.

Novel supramolecular organocatalysts of hydroxyprolinamide based on calix[4]arene scaffold for the enantioselective Biginelli reaction

Co-reporter:ZhengYi Li;HuaiJie Xing;GuoLi Huang;XiaoQiang Sun;JuLi Jiang

Science China Chemistry 2011 Volume 54( Issue 11) pp:1726-1734

Publication Date(Web):2011/11/01

DOI:10.1007/s11426-011-4374-z

A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supramolecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.

Synthesis, structural characterization of benzimidazole-functionalized Ni(II) and Hg(II) N-heterocyclic carbene complexes and their applications as efficient catalysts for Friedel–Crafts alkylations

Co-reporter:Guoli Huang, Hongsheng Sun, Xiaojie Qiu, Yingzhong Shen, Juli Jiang, Leyong Wang

Journal of Organometallic Chemistry 2011 696(18) pp: 2949-2957

Publication Date(Web):

DOI:10.1016/j.jorganchem.2011.04.039

High-performance Liquid Chromatography Study of the Nitration Course of Tetrabutoxycalix[4]arene at the Upper Rim: Determination of the Optimum Conditions for the Preparation of 5,11,17-Trinitro-25,26,27,28-tetrabutoxycalix[4]arene

Co-reporter:Zhengyi Li;Jiejie Ma;Jiawen Chen;Yi Pan;Juli Qiang;Leyong Wang

Chinese Journal of Chemistry 2009 Volume 27( Issue 10) pp:2031-2036

Publication Date(Web):

DOI:10.1002/cjoc.200990341

Abstract

A selective nitration of calix[4]arene at the upper rim in one pot process was described by monitoring the time dependence of the distribution of products by high-performance liquid chromatography (HPLC). The discrimination of five nitrated products was accomplished by molecular symmetry considerations and ¹H NMR analysis. As a result, unusual 5,11,17-trinitrocalix[4]arene (2d) was obtained in 57% isolated yield. 5,11-Dinitro-calix[4]arene (2b) and 5,11,17-trinitrocalix[4]arene (2d) with tetranitrocalix[4]arene 2e were further characterized by crystal X-ray diffraction analysis. Furthermore, as an example of potential application, trinitrocalix[4]arene 2d could be converted to triaminocalix[4]arene 3d conveniently.

The self-complexation of mono-urea-functionalized pillar[5]arenes with abnormal urea behaviors

Co-reporter:Mengfei Ni, Xiao-Yu Hu, Juli Jiang and Leyong Wang

Chemical Communications 2014 - vol. 50(Issue 11) pp:NaN1319-1319

Publication Date(Web):2013/11/08

DOI:10.1039/C3CC47823H

Mono-urea-functionalized pillar[5]arenes were prepared which exhibited abnormal urea behaviors. They were shown to form pseudo[1]rotaxanes with poor anion binding abilities in solution and [c2]daisy chains with an abnormal urea motif in the solid state.

4-Methylcoumarin-bridged fluorescent responsive cryptand: from [2+2] photodimerization to supramolecular polymer

Co-reporter:Ming Cheng, Chenhao Yao, Yihan Cao, Qi Wang, Yi Pan, Juli Jiang and Leyong Wang

Chemical Communications 2016 - vol. 52(Issue 56) pp:NaN8718-8718

Publication Date(Web):2016/06/06

DOI:10.1039/C6CC03624D

A fluorescent responsive BMP32C10-based cryptand host was successfully synthesized by introducing a 4-methylcoumarin group to the third arm of the cryptand. The cryptand was able to undergo [2+2] photodimerization on UV irradiation (λ = 365 nm) and, based on the photodimerization and host–guest interaction, a new supramolecular polymer was constructed in a convenient manner.

Redox-switchable host–guest systems based on a bisthiotetrathiafulvalene-bridged cryptand

Co-reporter:Qi Wang, Ming Cheng, Yue Zhao, Zhen Yang, Juli Jiang, Leyong Wang and Yi Pan

Chemical Communications 2014 - vol. 50(Issue 98) pp:NaN15588-15588

Publication Date(Web):2014/10/27

DOI:10.1039/C4CC07770A

By attaching a bisthiotetrathiafulvalene (STTFS) unit to the third arm of the cryptand, a redox-switchable bis(m-phenylene)-32-crown-10-based cryptand was synthesized successfully. It was found that the dethreading–rethreading processes between this cryptand and the guests could be well-controlled in different redox states owing to the specific redox-active properties of the STTFS unit.

Cu-catalyzed direct C–H bond functionalization: a regioselective protocol to 5-aryl thiazolo[3,2-b]-1,2,4-triazoles

Co-reporter:Zengyang Xie, Xiaojun Zhu, Yangfan Guan, Dunru Zhu, Hongwen Hu, Chen Lin, Yi Pan, Juli Jiang and Leyong Wang

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 8) pp:NaN1398-1398

Publication Date(Web):2012/12/12

DOI:10.1039/C2OB27326H

An efficient, regioselective C-5 arylation of thiazolo[3,2-b]-1,2,4-triazoles catalyzed by a simple copper catalyst was developed. This arylation proceeded smoothly and tolerated a variety of functional groups (44 examples). A wide range of functionalized thiazolo[3,2-b]-1,2,4-triazole derivatives were obtained in high yields (up to 99% yield). Possible catalytic cycles of the arylation were also discussed.

A pillar[5]arene-fused cryptand: from orthogonal self-assembly to supramolecular polymer

Co-reporter:Qi Wang, Ming Cheng, Yue Zhao, Lin Wu, Juli Jiang, Leyong Wang and Yi Pan

Chemical Communications 2015 - vol. 51(Issue 17) pp:NaN3626-3626

Publication Date(Web):2015/01/23

DOI:10.1039/C5CC00130G

A pillar[5]arene-fused cryptand with two different cavities was synthesized successfully. It was found that the novel tricyclic host could associate with two different guest species in an orthogonal manner. And based on this orthogonal self-assembly of two host–guest interactions, a novel type of supramolecular polymer was constructed easily and conveniently.

Squaramide-based tripodal receptors for selective recognition of sulfate anion

Co-reporter:Can Jin, Man Zhang, Lin Wu, Yangfan Guan, Yi Pan, Juli Jiang, Chen Lin and Leyong Wang

Chemical Communications 2013 - vol. 49(Issue 20) pp:NaN2027-2027

Publication Date(Web):2013/01/24

DOI:10.1039/C3CC00196B

Squaramide-based tripodal anion receptors 1–3 have been prepared and their anion binding properties with various inorganic anions were investigated. Receptor 1 formed a dimeric complex in solid state and a 1:1 complex in solution with SO42−. All receptors 1–3 could selectively encapsulate SO42−via hydrogen bonds over other examined anions.

PO functional group-containing cryptands: from supramolecular complexes to poly[2]pseudorotaxanes

Co-reporter:Qi Wang, Ming Cheng, Shuhan Xiong, Xiao-Yu Hu, Juli Jiang, Leyong Wang and Yi Pan

Chemical Communications 2015 - vol. 51(Issue 13) pp:NaN2670-2670

Publication Date(Web):2014/12/22

DOI:10.1039/C4CC09487E

Two types of cryptand-based host–guest complexes were constructed successfully, in which PO functional groups were located at the different positions of the third arms. Consequently, supramolecular poly[2]pseudorotaxanes with almost linear and zigzag shapes were formed in the solid state.