ChemBridge Research Laboratories Inc.

San Diego, CA, United States

ChemBridge Research Laboratories Inc.

San Diego, CA, United States
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Xie C.,Southwest University of Science and Technology | Hu W.,CAS Shanghai Advanced Research Institute | Hu W.,University of Chinese Academy of Sciences | Liu Y.A.,ChemBridge Research Laboratories Inc. | And 6 more authors.
Chinese Journal of Chemistry | Year: 2015

An improved partial oxidation of 1,4-dimethoxypillar[5]arene (DMP[5]) was described, through which selected pillar[n]arene[5-n]quinones, such as pillar[4]arene[1]quinone, pillar[3]arene[2]quinone, pillar[2]arene[3]quinone and pillar[1]arene[4]quinone, were synthesized by manipulating the ratio of oxidative reagent (NH4)2[Ce(NO3)6] to DMP[5]. Pillar[5]arene has been selectively oxidized to pillar[n]arene[5-n]quinones in relatively high yields and short reaction time. Copyright © 2015 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Tang B.,East China Normal University | Yang H.-M.,East China Normal University | Hu W.-J.,CAS Shanghai Advanced Research Institute | Ma M.-L.,East China Normal University | And 6 more authors.
European Journal of Organic Chemistry | Year: 2014

1,8-Dioxyanthracene-based bisarylene crown ethers, composed of ethylene glycol chains and aromatic moieties, have been synthesized. Complexation studies revealed that these crown ethers could form 1:1 complexes with methyl viologen dication (N,N′-dimethyl-4,4′-bipyridinium dication; MV2+) in a mixed solvent of CDCl3 and CD3CN (1:1 v/v) with association constants in a range of (1.2 ± 0.1) × 103 M -1 to (1.6 ± 0.2) × 104 M -1. The structure of the complex and the strength of the π-donor/π-acceptor interactions between the 1,8-dioxyanthracene planes and the pyridinium rings of MV2+ are highly dependent on the length of the polyether chains of the ethers. Structural analysis showed that the tetraethylene glycol-derived bis-1,8-dioxyanthracene-based crown ether 9 forms a U-shaped host-guest complex with MV2+ by inserting the coplanar pyridinium rings of MV2+ between the two parallel oriented 1,8-dioxyanthracene units of 9, which is driven predominantly by π-donor/π-acceptor interactions. The pentaethylene glycol-derived bis-1,8-dioxyanthracene-based crown ether 10, however, adopts a crescent-shaped conformation in complex 10MV2+ with the MV2+ guest being encapsulated by the polyether chains, propelled mainly by the hydrogen-bonding interactions between the hydrogen atoms of MV2+ and the oxygen atoms of the polyether chains of 10. Similarly, the hexaethylene glycol-derived bis-1,8-dioxyanthracene-based crown ether 11 forms a complex with MV2+. However, only weak π-donor/π-acceptor interactions between the aromatic groups of the mixed bisarylene crown ethers 12 and 13, and MV2+ were observed, and construction of tetracationic cyclophane [CBPQT4+] and crown ether 13 based [2]catenane 15 was achieved through supramolecular interactions between the [CBPQT4+] ring and naphtho unit in the crown ether. Sandwich and crescent conformations were adopted by bis-1,8-dioxyanthracene-based crown ethers upon complexation with methyl viologen dication (see Scheme). The structure of the complexes are highly dependent on the length of polyether chains of the crown ether. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Liu H.,CAS Shanghai Advanced Research Institute | Li X.-Y.,CAS Shanghai Advanced Research Institute | Zhao X.-L.,East China Normal University | Liu Y.A.,ChemBridge Research Laboratories Inc. | And 4 more authors.
Organic Letters | Year: 2014

Oxacalix[2]arene[2]pyrazine and functional polyether derived oxacalixcrown-6, -7, and -8 were synthesized, and their host-guest complexation with paraquat to form [2]pseudorotaxanes was studied. The [2]pseudorotaxanes were then successfully used in the construction of two oxacalixcrown-tetracationic cyclophane [CBPQT4+] based [2]catenanes. © 2014 American Chemical Society.


Hu W.-B.,CAS Shanghai Advanced Research Institute | Hu W.-B.,University of Chinese Academy of Sciences | Hu W.-J.,CAS Shanghai Advanced Research Institute | Liu Y.A.,ChemBridge Research Laboratories Inc. | And 4 more authors.
Organic Letters | Year: 2015

A pillar[5]arene-crown ether fused bicyclic host 1 was found to be able to recognize an imidazolium ion G1 by its pillar[5]arene subunit and a viologen ion G2 by its crown ether receptor discriminatively. The simultaneous binding of G1 and G2 by 1 resulted in the formation of a three-component host-guest complex G1⊂1⊃G2. Negative heterotropic cooperative effects were displayed by G1 and G2 in their binding to 1 and were investigated by stepwise bindings of G1 and G2 to 1. © 2015 American Chemical Society.


Hu W.-B.,East China Normal University | Yang H.-M.,East China Normal University | Hu W.-J.,CAS Shanghai Advanced Research Institute | Ma M.-L.,East China Normal University | And 8 more authors.
Chemical Communications | Year: 2014

A bicyclic host molecule 1 consisting of a pillar[5]arene and a 1,5-dioxynaphthalene-based crown ether unit has been synthesized, and the two cyclic subunits in 1 were found to recognize two different guest molecules (1,4-dicyanobutane and paraquat) selectively or take up the two guest molecules simultaneously. This journal is © the Partner Organisations 2014.


Hu W.-J.,CAS Shanghai Advanced Research Institute | Liu L.-Q.,East China Normal University | Ma M.-L.,East China Normal University | Zhao X.-L.,East China Normal University | And 5 more authors.
Inorganic Chemistry | Year: 2013

A novel trispyrazine-pillared prismatic bicycooxacalixaromatic ligand L is synthesized, and its application in metal-mediated self-assembly is described. Under self-assembly conditions, single chain, double-stranded cross-linked coordination polymer and two-dimensional (2D) coordination polymeric networks were formed via M-L (Ag+, Cu2+, and Zn2+) coordinative interactions. Structural analyses revealed that the antiparallelly arranged one-dimensional coordination polymers (Cu2+ and Zn 2+) are arranged to generate well-defined voids to host aromatic guests (benzene) via C-H⋯π and π⋯π interactions, while the double-stranded cross-linked coordination polymer (Ag+) contains a rhomboidal [Ag2(L3)2] (L3: tridentate ligand) cage motif to include a benzene guest; the "thicker" (thickness: ac 5 Å) 2D coordination polymeric networks (Ag+, Cu2+, and Zn2+), however, are all formed by connection of one or two kinds of topologically different metallomacrocyclic cage units. These unique metallomacrocyclic cage units in the 2D coordination polymeric networks are capable of hosting different guest species. For instance, the rhomboidal [M2(L3)2] (M = Ag+, Cu2+) cage units were found to host a benzene or a nitrate anion; a hexahedral [M3(L3)3] (M = Ag+) cage was found to host a ligand L or a DMF molecule; the hexahedral [M 4(L3)4] (M = Cu2+) cage was found to host four solvent molecules of benzene; and the rectangular [M 3(L3)3] (M = Cu2+, Zn2+) cage units, however, were found to host two THF molecules. The results highlight the potential of ligand L for applications in the construction of "thicker" 2D coordination polymeric networks with well-defined metallomacrocyclic cage units capable of hosting various guest species. © 2013 American Chemical Society.


Hu W.-J.,CAS Shanghai Advanced Research Institute | Liu L.-Q.,East China Normal University | Ma M.-L.,East China Normal University | Zhao X.-L.,East China Normal University | And 5 more authors.
Tetrahedron | Year: 2013

The synthesis of oxacalix[2]terphenylene[2]aromatics with enlarged macrocyclic holes by cyclooligomerization reaction of 5′-tert-butyl-(1, 1′:3′,1″-terphenyl)-3,3″-diol 1 with electron-deficient dihalogenated benzene and azaheterocycles is described. The structures of the macrocycles were characterized by NMR, HRMS spectroscopic and X-ray diffraction techniques. Single crystal X-ray analysis revealed that the terphenyl-3, 3″-dioxo unit incorporated in the oxacalix[4]aromatics scaffold can adopt all three possible conformations (I, II, III). The cis-conformational terphenyl-3,3″-dioxo (I and II) derived oxacalix[4]aromatics were found to adopt both chair and boat conformations, resulted in creation of molecular cavities capable of hosting solvent molecules of chloroform. The trans-conformational terphenyl-3,3″-dioxo (III) derived oxacalix[4]aromatics, however, adopt a twisted chair conformation with a narrow void space incapable of hosting any guest molecules.© 2013 Elsevier Ltd. All rights reserved.


Li X.-Y.,East China Normal University | Hu C.,East China Normal University | Ma M.-L.,East China Normal University | Liu Y.A.,ChemBridge Research Laboratories Inc. | And 4 more authors.
Chinese Chemical Letters | Year: 2013

Oxacalixcrowns 1, 2 and 3 were synthesized via reactions of dihydroxyoxacalix[2]arene[2]pyrazine 5 with ortho-, meta- and para-bis(bromomethyl)benzenes in a 1:1 fashion. The structures and conformations of 1, 2 and 3 were established by a combination of NMR, mass spectroscopies and single crystal X-ray diffraction analysis. © 2013 Ming-Liang Ma.


PubMed | ChemBridge Research Laboratories Inc. and CAS Shanghai Advanced Research Institute
Type: Journal Article | Journal: Organic letters | Year: 2015

A pillar[5]arene-crown ether fused bicyclic host 1 was found to be able to recognize an imidazolium ion G1 by its pillar[5]arene subunit and a viologen ion G2 by its crown ether receptor discriminatively. The simultaneous binding of G1 and G2 by 1 resulted in the formation of a three-component host-guest complex G11G2. Negative heterotropic cooperative effects were displayed by G1 and G2 in their binding to 1 and were investigated by stepwise bindings of G1 and G2 to 1.


PubMed | East China Normal University, CAS Shanghai Advanced Research Institute, Southwest University of Science and Technology and ChemBridge Research Laboratories Inc.
Type: Journal Article | Journal: The Journal of organic chemistry | Year: 2015

A novel tricylic host molecule 1 that consists of two pillar[5]arene units and a crown ether ring was found to selectively bind two kinds of guest molecules with different shapes, sizes, and electronic constitutions, namely 1,4-dicyanobutane G1 and paraquat G2, with its two macrocyclic subunits, to form a four-component complex 2G11G2. An (1)H NMR study of stepwise bindings of G1 and G2 to host 1 in CDCl3/DMSO-d6 revealed that the strength of the association between complex 2G11 and guest G2 was only one-fourth of that between free 1 and G2, demonstrating a negative heterotropic cooperativity of G1 in the binding of G2 to host 1.

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