- Atomic-scale visualization of stepwise growth mechanism of metal-alkynyl networks on surfaces
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One of the most appealing topics in the study of metal?organic networks is the growth mechanism. However, its study is still considered a significant challenge. Herein, using scanning tunneling microscopy, the growth mechanisms of metal? alkynyl networks
- Chen, Jian-Le,He, Yan,Liu, Pei-Nian,Shu, Chen-Hui,Wang, An,Zhang, Ruo-Xi
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Read Online
- The potential of a graphene-supported porous-organic polymer (POP) for CO2 electrocatalytic reduction
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A one-pot, bottom-up assembly of a pyrimidine-containing porous-organic polymer (PyPOP) was conducted to homogenously deposit the PyPOP atop unmodified graphene sheets, affording a composite material PyPOP@G. The PyPOP demonstrated an appreciable affinity toward CO2 capture but was found to be largely insulating, hindering its usage in potential electrochemical conversion of CO2. However, its composite with graphene was found to be microporous, with maintained affinity toward CO2 and furthermore demonstrated significant electrochemical activity toward CO2 reduction (5 mA cm-2 at -1.6 V), not observed in either of its two components separately.
- Soliman, Ahmed B.,Haikal, Rana R.,Hassan, Youssef S.,Alkordi, Mohamed H.
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Read Online
- Synthesis and luminescence properties of Ru2/Cu, Ru2/Ni, and Ru2/Os mixed metal polypyridine complexes bound by 1,3,5-triethynylenebenzene
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Novel polypyridine metal complexes have been prepared, wherein two (terpy)2Ru units and one (bipy)3M (M=Cu, Os) or (bipy)Ni(H2O)4 unit (terpy= 2,2':6,6'-terpyridine, bipy= 2,2'-bipyridine) are bonded to 1,3,5-po
- Osawa, Masahisa,Sonoki, Hirotaka,Hoshino, Mikio,Wakatsuki, Yasuo
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Read Online
- Toward the synthesis, fluorination and application of N-graphyne
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The discovery of properties and applications of unknown materials is one of the hottest research areas in materials science. In this work, we navigate a route towards these goals by the development of a new type of graphyne nanostructure. It is synthesise
- Abdi, Gisya,Cichowicz, Grzegorz,Fija?kowski, Karol J.,Filip, Anna,Hamankiewicz, Bartosz,Kazimierczuk, Krzysztof,Krajewski, Micha?,Leszczyński, Piotr J.,Mazej, Zoran,Strawski, Marcin,Szarek, Pawe?,Szczurek, Andrzej
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Read Online
- Metal-Free Catalysis: A Redox-Active Donor-Acceptor Conjugated Microporous Polymer for Selective Visible-Light-Driven CO2Reduction to CH4
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Achieving more than a two-electron photochemical CO2reduction process using a metal-free system is quite exciting and challenging, as it needs proper channeling of electrons. In the present study, we report the rational design and synthesis of
- Barman, Soumitra,Maji, Tapas Kumar,Rahimi, Faruk Ahamed,Singh, Ashish
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supporting information
p. 16284 - 16292
(2021/10/12)
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- Layered supramolecular network of cyclodextrin triplets with azobenzene-grafting polyoxometalate for dye degradation and partner-enhancement
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A tri-β-cyclodextrin-armed host compound is synthesized to construct layered supramolecular network co-assembly with a doubly azobenzene-decorated polyoxometalate cluster through host-guest interaction. The porous hybrid assembly displays automatic degrad
- Gao, Bo,Li, Bao,Wu, Lixin
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supporting information
p. 10512 - 10515
(2021/10/19)
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- Synthesis of Rigid Rod, Trigonal, and Tetrahedral Nucleobase-Terminated Molecules
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An efficient fragment splicing method for the construction of multiple nucleobase-terminated monomers has been developed. Conformationally fixed rod, trigonal planar and tetrahedral thymine and adenine structures were generated in moderate to good yields,
- Cheng, Liang,Jin, Xiao-Yang,Liu, An-Di,Liu, Li,Wu, Chuan-Shuo
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- PHOSPHINE OXIDE COMPOUND, RARE EARTH COMPLEX, AND LIGHT-EMITTING MATERIAL
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A phosphine oxide compound represented by the following formula (I) and a rare earth complex containing the same are disclosed: wherein n represents an integer of 3 or more, Ar1 represents an n-valent aromatic group, L represents a divalent linker group, and Ar2 and Ar3 each independently represent a monovalent aromatic groups.
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Paragraph 0038-0039; 0042-0044
(2021/05/07)
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- Thermogravimetric Analysis and Mass Spectrometry Allow for Determination of Chemisorbed Reaction Products on Metal Organic Frameworks
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Thermogravimetric analysis (TGA) is a technique which can probe chemisorption of substrates onto metal organic frameworks. A TGA method was developed to examine the catalytic oxidation of S-nitrosoglutathione (GSNO) by the MOF H3[(Cu4Cl)3(BTTri)8] (abbr. Cu-BTTri; H3BTTri = 1,3,5-tris(1H-1,2,3-triazol-5-yl)benzene), yielding glutathione disulfide (GSSG) and nitric oxide (NO). Thermal analysis of reduced glutathione (GSH), GSSG, GSNO, and Cu-BTTri revealed thermal resolution of all four analytes through different thermal onset temperatures and weight percent changes. Two reaction systems were probed: an aerobic column flow reaction and an anaerobic solution batch reaction with gas agitation. In both systems, Cu-BTTri was reacted with a 1 mM GSH, GSSG, or GSNO solution, copiously rinsed with distilled-deionized water (dd-H2O), dried (25 °C, 1 Torr), and assessed by TGA. Additionally, stock, effluent or supernatant, and rinse solutions for each glutathione derivative within each reaction system were assessed by mass spectrometry (MS) to inform on chemical transformations promoted by Cu-BTTri as well as relative analyte concentrations. Both reaction systems exhibited chemisorption of glutathione derivatives to the MOF by TGA. Mass spectrometry analyses revealed that in both systems, GSH was oxidized to GSSG, which chemisorbed to the MOF whereas GSSG remained unchanged during chemisorption. For GSNO, chemisorption to the MOF without reaction was observed in the aerobic column setup, whereas conversion to GSSG and subsequent chemisorption was observed in the anaerobic batch setup. These findings suggest that within this reaction system, GSSG is the primary adsorbent of concern with regards to strong binding to Cu-BTTri. Development of similar thermal methods could allow for the probing of MOF reactivity for a wide range of systems, informing on important considerations such as reduced catalytic efficiency from poisoning, recyclability, and loading capacities of contaminants or toxins with MOFs.
- Jones, W. Matthew,Reynolds, Melissa M.,Tapia, Jesus B.,Tuttle, Robert R.
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p. 3903 - 3911
(2020/05/04)
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- Polysubstituted chloroethynyl benzene compound as well as preparation method and application thereof
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The invention provides a polysubstituted chloroethynyl benzene compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The polysubstituted chloroethynyl benzene compound provided by the in
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Paragraph 0078-0080
(2020/10/20)
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- Ultrafine silver nanoparticles supported on a covalent carbazole framework as high-efficiency nanocatalysts for nitrophenol reduction
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A novel conjugated microporous polymer (CMP) material CZ-TEB was synthesized with a carbazole analogue and 1,3,5-triethynylbenzene. It possessed a high specific surface area, excellent thermal stability and layered-sheet morphology. Furthermore, ultrafine silver nanoparticles were successfully immobilized on CZ-TEB, thus preparing a nanocatalyst Ag0@CZ-TEB. To evaluate its catalytic performance, Ag0@CZ-TEB was exploited in the reduction reaction of nitrophenols, a family of priority pollutants. Ag0@CZ-TEB exhibited high catalytic ability, convenient recovery and excellent reusability. Strikingly, the normalized rate constant (knor) of the reduction reaction of 4-NP to 4-AP is as high as 21.49 mmol-1 s-1. This result shows a significant improvement over all previously reported work. We purposed to use a "capture-release" model to explain the high catalytic ability of Ag0@CZ-TEB. This explanation is supported by further experimental results that agree well with the "capture-release" model.
- Gong, Wei,Wu, Qianqian,Jiang, Guoxing,Li, Guangji
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supporting information
p. 13449 - 13454
(2019/06/13)
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- Gfp chromophore integrated conjugated microporous polymers: Topological and ESPT effects on emission properties
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A metal free topological approach is demonstrated to mimic the photophysical properties of natural gfp by synthesizing two gfp chromophore integrated conjugated microporous polymers (o-HBDI-TEB-CMP and o-MBDI-TEB-CMP). Interestingly, owing to the structur
- Singh, Ashish,Samanta, Debabrata,Boro, Mrinal,Maji, Tapas Kumar
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supporting information
p. 2837 - 2840
(2019/03/06)
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- Sonogashira Couplings Catalyzed by Fe Nanoparticles Containing ppm Levels of Reusable Pd, under Mild Aqueous Micellar Conditions
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Nanoparticles derived from FeCl3 containing the ligand XPhos and only 500 ppm Pd effect Sonogashira couplings in water between rt and 45 °C. The entire aqueous reaction medium can be easily recycled using an "in-flask" extraction. Several tande
- Handa, Sachin,Jin, Bo,Bora, Pranjal P.,Wang, Ye,Zhang, Xiaohua,Gallou, Fabrice,Reilly, John,Lipshutz, Bruce H.
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p. 2423 - 2431
(2019/03/08)
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- Interplay between H-Bonding and Preorganization in the Evolution of Self-Assembled Systems
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Cooperative π–π interactions and H-bonding are frequently exploited in supramolecular polymerization; however, close scrutiny of their mutual interplay has been largely unexplored. Herein, we compare the self-assembly behavior of a series of C2
- Philips, Divya S.,Kartha, Kalathil K.,Politi, Antiope T.,Krüger, Timo,Albuquerque, Rodrigo Q.,Fernández, Gustavo
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supporting information
p. 4732 - 4736
(2019/03/08)
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- Copper ion vs copper metal–organic framework catalyzed NO release from bioavailable S-Nitrosoglutathione en route to biomedical applications: Direct 1H NMR monitoring in water allowing identification of the distinct, true reaction stoichiometries and thiol dependencies
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Copper containing compounds catalyze decomposition of S-Nitrosoglutathione (GSNO) in the presence of glutathione (GSH) yielding glutathione disulfide (GSSG) and nitric oxide (NO). Extended NO generation from an endogenous source is medically desirable to achieve vasodilation, reduction in biofilms on medical devices, and antibacterial activity. Homogeneous and heterogeneous copper species catalyze release of NO from endogenous GSNO. One heterogeneous catalyst used for GSNO decomposition in blood plasma is the metal-organic framework (MOF), H3[(Cu4Cl)3-(BTTri)8, H3BTTri = 1,3,5-tris(1H-1,2,3-triazol-5-yl) benzene] (CuBTTri). Fundamental questions about these systems remain unanswered, despite their use in biomedical applications, in part because no method previously existed for simultaneous tracking of [GSNO], [GSH], and [GSSG] in water. Tracking these reactions in water is a necessary step towards study in biological media (blood is approximately 80% water) where NO release systems must operate. Even the balanced stoichiometry remains unknown for copper-ion and CuBTTri catalyzed GSNO decomposition. Herein, we report a direct 1H NMR method which: simultaneously monitors [GSNO], [GSH], and [GSSG] in water; provides the experimentally determined stoichiometry for copper-ion vs CuBTTri catalyzed GSNO decomposition; reveals that the CuBTTri-catalyzed reaction reaches 10% GSNO decomposition (16 h) without added GSH, yet the copper-ion catalyzed reaction reaches 100% GSNO decomposition (16 h) without added GSH; and shows 100% GSNO decomposition upon addition of stoichiometric GSH to the CuBTTri catalyzed reaction. These observations provide evidence that copper-ion and CuBTTri catalyzed GSNO decomposition in water operate through different reaction mechanisms, the details of which can now be probed by 1H NMR kinetics and other needed studies.
- Tuttle, Robert R.,Rubin, Heather N.,Rithner, Christopher D.,Finke, Richard G.,Reynolds, Melissa M.
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- Coordination-driven self-assembly of discrete Ru6–Pt6 prismatic cages
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The coordination-driven self-assembly of two new Ru6–Pt6 hexanuclear trigonal prismatic cages comprising arene–ruthenium(II) clips (1a(NO3)2 and 1b(NO3)2) and a tritopic platinum(II) metall
- Adeyemo, Aderonke Ajibola,Mukherjee, Partha Sarathi
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supporting information
p. 2242 - 2249
(2018/09/04)
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- Tridentate Lewis Acids: Silicon-Functionalised 1,3,5-Triethynylbenzene and 1,3,5-Trivinylbenzene
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Planar tridentate Lewis acids were synthesised by hydrosilylation reactions of triethynylbenzene with chlorosilanes. Hydrogenation of the rigid triethynylbenzene using hydrogen in the presence of Lindlar's catalyst resulted in the formation of trivinylben
- Schwartzen, Anna,Siebe, Lena,Schwabedissen, Jan,Neumann, Beate,Stammler, Hans-Georg,Mitzel, Norbert W.
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p. 2533 - 2540
(2018/06/04)
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- Sustainable HandaPhos-ppm Palladium Technology for Copper-Free Sonogashira Couplings in Water under Mild Conditions
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Complexation of ca. 1000 ppm Pd(OAc)2 with the ligand HandaPhos (1-1.5:1) leads to a precatalyst that efficiently mediates Sonogashira couplings in aqueous nanomicelles under very mild conditions. Neither copper nor organic solvent is required
- Handa, Sachin,Smith, Justin D.,Zhang, Yitao,Takale, Balaram S.,Gallou, Fabrice,Lipshutz, Bruce H.
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supporting information
p. 542 - 545
(2018/02/10)
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- Stronger host-guest binding does not necessarily give brighter particles: a case study on polymeric AIEE-tunable and size-tunable supraspheres
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Supraspheres were prepared from a pillar[5]arene-based linear polymer (the host) and several multitopic guests. According to host-guest binding studies in nanosystems, the optical and structural properties (fluorescence capability, density, and particle s
- Xu, Linxian,Wang, Rongrong,Cui, Wei,Wang, Lingyun,Meier, Herbert,Tang, Hao,Cao, Derong
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supporting information
p. 9274 - 9277
(2018/08/31)
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- Direct Enzymatic Branch-End Extension of Glycocluster-Presented Glycans: An Effective Strategy for Programming Glycan Bioactivity
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The sequence of a glycan and its topology of presentation team up to determine the specificity and selectivity of recognition by saccharide receptors (lectins). Structure–activity analysis would be furthered if the glycan part of a glycocluster could be efficiently elaborated in situ while keeping all other parameters constant. By using a bacterial α2,6-sialyltransferase and a small library of bi- to tetravalent glycoclusters, we illustrate the complete conversion of scaffold-presented lactoside units into two different sialylated ligands based on N-acetyl/glycolyl-neuraminic acid incorporation. We assess the ensuing effect on their bioactivity for a plant toxin, and present an analysis of the noncovalent substrate binding contacts that the added sialic acid moiety makes to the lectin. Enzymatic diversification of a scaffold-presented glycan can thus be brought to completion in situ, offering a versatile perspective for rational glycocluster engineering.
- Bayón, Carlos,He, Ning,Deir-Kaspar, Mario,Blasco, Pilar,André, Sabine,Gabius, Hans-Joachim,Rumbero, ángel,Jiménez-Barbero, Jesús,Fessner, Wolf-Dieter,Hernáiz, María J.
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supporting information
p. 1623 - 1633
(2017/02/10)
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- Chiral induction, transfer and modulation in C 3-symmetric columnar liquid crystalline assemblies
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Circularly polarized light (CPL), regarded as a true chiral entity, has been suggested as one possible origin of homochirality in nature. It still remains difficult to understand the exact mechanism of chiral induction, transfer and amplification in supramolecular assemblies. Herein, we designed and synthesized three discotic diacetylene LC monomers, in which the peripheral diacetylene flexible chains linked to the triazole derivative cores through H-bonding or covalent bonds. We established links between the primary chemical structures of discotic diacetylene monomers, liquid crystal phase structures and optically active properties in the final supramolecular assemblies. Moreover, the type of junction bonding interaction exhibited a significant influence on the chiral transfer in a supramolecular columnar LC system.
- Hu, Jingang,Zhu, Tianyi,He, Chenlu,Zhang, Yan,Zhang, Qijin,Zou, Gang
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supporting information
p. 5135 - 5142
(2017/07/10)
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- Heterometallic Cu(I)/Ru(II) halide and pseudohalide hybrid complexes composed of coordination and organometallic sites: Synthesis, spectroscopic characterization, electrochemical and luminescence properties
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A new series of heterometallic halide/pseudohalide hybrid complexes of the type [Cu(L1)NC5H4–C[tbnd]C–C6H3–1,3-{C[tbnd]C-trans-RuCl(dppe)2}2X] (1a–d) and [Cu(L2)NCsub
- Pawal,Lolage,Chavan
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p. 112 - 120
(2017/03/27)
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- Efficient and straightforward click synthesis of structurally related dendritic triazoles
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A simple, rapid and efficient copper-catalyzed 1,3-dipolar cycloaddition reaction is described for the synthesis of a novel family of twelve triazolic dendrimers structurally related. The products were the result of the click reaction of three cores and four different azides in tetrahydrofuran applying a homogeneous copper catalysis. The reaction intermediates and products were obtained in very good to excellent yields using straightforward and simple work-up procedures. This new family of compounds contain electroactive moieties such as carbazole and triphenylamine which may turn them into excellent candidates for the development of optoelectronic organic materials.
- Mangione,Spanevello,Anzardi
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p. 47681 - 47688
(2017/10/23)
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- Electrochemically active porous organic polymers based on corannulene
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For the first time, porous organic polymers (POPs) based on the smallest buckybowl, corannulene (BB-POPs) have been synthesized. Three POPs were synthesised via Sonogashira co-polymerization of 1,2,5,6-tetrabromocorannulene and alkyne linkers. BB-POP-3 exhibits the highest surface area (SABET = 560 m2 g-1) and CO2 adsorption of 11.7 wt%, while they retain the redox properties of corannulene.
- Karunathilake, Arosha A.K.,Thompson, Christina M.,Perananthan, Sahila,Ferraris, John P.,Smaldone, Ronald A.
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supporting information
p. 12881 - 12884
(2016/11/06)
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- Two-Dimensional Core-Shelled Porous Hybrids as Highly Efficient Catalysts for the Oxygen Reduction Reaction
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Two-dimensional (2D) transition-metal dichalcogenides (TMDs) have drawn much attention due to their unique physical and chemical properties. Using TMDs as templates for the generation of 2D sandwich-like materials with remarkable properties still remains
- Yuan, Kai,Zhuang, Xiaodong,Fu, Haiyan,Brunklaus, Gunther,Forster, Michael,Chen, Yiwang,Feng, Xinliang,Scherf, Ullrich
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supporting information
p. 6858 - 6863
(2016/06/13)
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- Conjugated porous polymers as precursors for electrocatalysts and storage electrode materials
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Conjugated porous polymers were used as precursors to prepare nitrogen and sulphur doped carbon atoms, which were then used for oxygen reduction and energy storage.
- Bhosale, Manik E.,Illathvalappil, Rajith,Kurungot, Sreekumar,Krishnamoorthy, Kothandam
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supporting information
p. 316 - 318
(2016/01/09)
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- Star-shaped triphenylene discotic liquid crystalline oligomers and their hydrogen-bonded supramolecular complexes with simple acids
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The synthesis and self-assembly properties of four novel star-shaped oligomers containing triphenylene discotic mesogens are reported. These materials have been synthesized in good yields by the Cu-catalyzed coupling cycloaddition reaction (CuAAC) between
- Zhao, Ke-Qing,Bai, Xiao-Yan,Xiao, Bo,Gao, Yue,Hu, Ping,Wang, Bi-Qin,Zeng, Qing-Dao,Wang, Chen,Heinrich, Beno?t,Donnio, Bertrand
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p. 11735 - 11746
(2015/11/17)
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- Bestowing structure upon the pores of a supramolecular network
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Trigonal molecules compartmentalise the pores of a honeycomb network of 3,4:9,10-tetracarboxylic diimide (PTCDI) and 1,3,5-triazine-2,4,6-triamine (melamine). Extending the 1,3,5-tri(phenylene-ethynylene)benzene core by a phenyl group allows for a well-defined accommodation of the molecule into two symmetry equivalent positions in the pore. The corresponding styryl or phenylene-ethynylene derivatives exceed the pore size and, thus, impede pore modification. This journal is
- Karamzadeh, Baharan,Eaton, Thomas,Cebula, Izabela,Torres, David Muoz,Neuburger, Markus,Mayor, Marcel,Buck, Manfred
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supporting information
p. 14175 - 14178
(2015/01/09)
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- Efficient fixation of CO2 by a zinc-coordinated conjugated microporous polymer
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Zinc-coordinated conjugated microporous polymers (Zn-CMPs), prepared by linking salen zinc and 1,3,5-triethynylbenzene, exhibit extraordinary activities (turnover frequencies of up to 11600 h-1), broad substrate scope, and group tolerance for the synthesis of functional organic carbonates by coupling epoxides with CO2 at 120 °C and 3.0 MPa without the use of additional solvents. The catalytic activity of Zn-CMP is comparable to those of homogeneous catalysts and superior to those of other heterogeneous catalysts. This catalyst could be reused more than ten times without a significant decrease in performance.
- Xie, Yong,Wang, Ting-Ting,Yang, Rui-Xia,Huang, Nian-Yu,Zou, Kun,Deng, Wei-Qiao
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p. 2110 - 2114
(2014/10/15)
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- Novel planar and star-shaped molecules: Synthesis, electrochemical and photophysical properties
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Three novel planar and star-shaped molecules containing thiophene-functionalized group and acetylenic spacers, 4-((5″-iodo-[2, 2′:5′,2″-terthiophen]-5-yl)ethynyl)aniline (I3TEA), 4,4′-([2,2′:5′,2″-terthiophene]-5,5″- diylbis(ethyne-2,1-diyl))dianiline (3T
- Niu, Qingfen,Lu, Yunqiang,Sun, Hongjian,Li, Xiaoyan
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p. 377 - 385
(2013/05/08)
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- Synthesis, spectroscopic characterization and structural investigation of a new symmetrically trisubstituted benzene derivative: 3,3′, 3′′-(Benzene-1,3,5-triyl)tripropiolic acid
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The new 1,3,5-trisubstituted benzene derivative 1 featuring three propiolic acid side arms symmetrically attached to a benzene core has been synthesized. Spectroscopic studies including 1H and 13C NMR as well as FTIR measurements wer
- Münch, Alexander S.,Katzsch, Felix,Weber, Edwin,Mertens, Florian O.R.L.
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p. 103 - 108
(2013/06/27)
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- Electrogenerated conductive polymers from triphenylamine end-capped dendrimers
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Electroactive end-capped dendritic macromolecules were designed and synthesized. Their structures contain triphenylamine moieties as part of the core or dendrons. The electrogenerated films produced with these monomers behaved as conductive dendritic poly
- Mangione, Maria I.,Spanevello, Rolando A.,Rumbero, Angel,Heredia, Daniel,Marzari, Gabriela,Fernandez, Luciana,Otero, Luis,Fungo, Fernando
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p. 4754 - 4763
(2013/07/26)
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- Conjugated poly(aryleneethynylenesiloles) and their application in detecting explosives
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Hyperbranched and linear conjugated polysiloles incorporating arylene ethynylene subunits (6 and 7) were synthesized by the Sonogashira reaction. The two polymers possess unusual phenomena of PL, with gradual addition of water in their THF solution, the intensity of PL firstly increased and then decreased, this may be due to the aggregate-enhanced emission (AEE) effect and aggregation-caused quenching (ACQ) effect. The polymers function as sensitive fluorescent chemosensors for the detection of explosives, such as picric acid (PA) and TNT. The quenching constants of 6 for PA and TNT were 4.7 × 10-2 ppm-1 and 4.6 × 10-3 ppm -1, respectively. The quenching constants of 7 for PA and TNT were 8.6 × 10-2 ppm-1 and 6.5 × 10-3 ppm-1 respectively. The polymer 7 has more detective efficiency for PA and TNT than that of polymer 6, this may be due to the less steric hindrance.
- Shu, Weifu,Guan, Changwei,Guo, Wenhao,Wang, Chengyun,Shen, Yongjia
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experimental part
p. 3075 - 3081
(2012/06/01)
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- Synthesis of conjugated aryleneethynylenesiloles dendron
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Three routes were designed to synthesize a π-conjugated aryleneethynylenesiloles dendron. With the desilylation of the disilole mono(silylethynyl) derivative in the presence of potassium carbonate (K 2CO3), the silole-containing oligomer has been successfully synthesized without impact on the Si-(CH3)2 group. The disilole mono(silylethynyl) derivative was prepared by means of the Sonogashira heterocoupling reaction between the diacetylene compound and asymmetrical silole, catalyzed by the dichloro bis(triphenylphosphine)palladium, in a divergent synthesis. Due to their steric effect and triethynylbenzene self-coupling Glaser reaction, the endeavour to prepare the dendron by controlling the molar ratio of asymmetrical silole and 1,3,5-triethynylbenzene was failed. The another attempt to prepare the dendron by different desilylation condition of triisopropylsilyl group and trimethylsilyl group was also failed, the desilylation of Si-(CH3)2 group in silacyclopentadiene unit was also easily accomplished in the presence of tetrabutylammonium fluoride(Bu4NF), whereas no reaction occurred when K 2CO3 was used instead of Bu4NF. Copyright
- Liu, Jie,Yan, Chenxu,Li, Shanshan,Wang, Chengyun,Shen, Yongjia
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p. 2861 - 2868
(2013/08/23)
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- Supramolecular tetrahedra of phosphines and coinage metals
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Treasure chests: The Group 11 metals CuI, AgI, and AuI form tetrahedral supramolecular clusters with a rigid threefold-symmetric phosphine ligand. These supramolecular clusters, which assemble by metal-phosphine interactio
- Lim, Sang Ho,Su, Yongxuan,Cohen, Seth M.
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supporting information; experimental part
p. 5106 - 5109
(2012/07/16)
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- Designed synthesis of a metal cluster-pillared coordination cage
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An unprecedented polynuclear metal cluster-pillared triangular prism was built by a macrocycle-directing strategy. Discrete architectures of three silver cluster-involved metallosupramolecules were characterized by single crystal X-ray crystallography and
- He, Xin,Gao, Cai-Yan,Wang, Mei-Xiang,Zhao, Liang
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supporting information
p. 10877 - 10879,3
(2012/12/12)
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- Designed synthesis of a metal cluster-pillared coordination cage
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An unprecedented polynuclear metal cluster-pillared triangular prism was built by a macrocycle-directing strategy. Discrete architectures of three silver cluster-involved metallosupramolecules were characterized by single crystal X-ray crystallography and
- He, Xin,Gao, Cai-Yan,Wang, Mei-Xiang,Zhao, Liang
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supporting information
p. 10877 - 10879
(2013/01/15)
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- Structural rules for the chiral supramolecular organization of OPE-based discotics: Induction of helicity and amplification of chirality
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A systematic study on the structural rules that regulate the chiral supramolecular organization of oligo(phenylene ethynylene) (OPE)-based discotics is presented. This study is based on the chirooptical properties of two different series of triangular sha
- Garcia, Fatima,Sanchez, Luis
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supporting information; scheme or table
p. 734 - 742
(2012/03/08)
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- A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols
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Tetrabutylammonium hydroxide with methanol as an additive was found to be a highly active catalyst for the cleavage of 4-aryl-2-methyl-3-butyn-2-ols. The reaction was performed at 55-75 °C and gave terminal arylacetylenes in good to excellent yields within several minutes. Compared with the usual reaction conditions (normally >110 °C, several hours), this novel catalyst system can dramatically decrease the reaction time under much milder conditions.
- Li, Jie,Huang, Pengcheng
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experimental part
p. 426 - 431
(2011/06/11)
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- Complementary hydrogen bonding between a clicked C3-symmetric triazole derivative and carboxylic acids for columnar liquid-crystalline assemblies
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Two's complement: A series of discotic hydrogen-bonded complexes was prepared from a "clicked" triazole derivative with C3 symmetry and carboxylic acids (see picture; R1, R2=alkyl groups). Owing to the extended rigid core
- Ryu, Mi-Hee,Choi, Jin-Woo,Kim, Ho-Joong,Park, Noejung,Cho, Byoung-Ki
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supporting information; experimental part
p. 5737 - 5740
(2011/08/06)
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- From molecular to macroscopic engineering: Shaping hydrogen-bonded organic nanomaterials
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The self-assembly and self-organization behavior of chromophoric acetylenic scaffolds bearing 2,6-bis(acetylamino)pyridine (1, 2) or uracyl-type (3-9) terminal groups has been investigated by photophysical and microscopic methods. Systematic absorption and luminescence studies show that 1 and 2, thanks to a combination of solvophilic/solvophobic forces and π-π stacking interactions, undergo self-organization in apolar solvents (i.e., cyclohexane) and form spherical nanoparticles, as evidenced by wide-field optical microscopy, TEM, and AFM analysis. For the longer molecular module, 2, a more uniform size distribution is found (80-200nm) compared to 1 (20-1000nm). Temperature scans in the range 283-353K show that the self-organized nanoparticles are reversibly formed and destroyed, being stable at lower temperatures. Molecular modules 1 and 2 were then thoroughly mixed with the complementary triply hydrogen-bonding units 3-9. Depending on the specific geometrical structure of 3-9, different nanostructures are evidenced by microscopic investigations. Combination of modules 1 or 2 with 3, which bears only one terminal uracyl unit, leads to the formation of vesicular structures; instead, when 1 is combined with bis-uracyl derivative 4 or 5, a structural evolution from nanoparticles to nanowires is observed. The length of the wires obtained by mixing 1 and 4 or 1 and 5 can be controlled by addition of 3, which prompts transformation of the wires into shorter rods. The replacement of linear system 5 with the related angular modules 6 and 7 enables formation of helical nanostructures, unambiguously evidenced by AFM. Finally, thermally induced self-assembly was studied in parallel with modules 8 and 9, in which the uracyl recognition sites are protected with tert-butyloxycarbonyl (BOC) groups. This strategy allows further control of the self-assembly/self-organization process by temperature, since the BOC group is completely removed on heating. Microscopy studies show that the BOC-protected ditopic modules 8 self-assemble and self-organize with 1 into ordered linear nanostructures, whereas BOC-protected tritopic system 9 gives rise to extended domains of circular nano-objects in combination with 1.
- Yoosaf,Llanes-Pallas, Anna,Marangoni, Tomas,Belbakra, Abdelhalim,Marega, Riccardo,Botek, Edith,Champagne, Beno?t,Bonifazi, Davide,Armaroli, Nicola
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supporting information; experimental part
p. 3262 - 3273
(2011/04/24)
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- Calix[4]bis(spirodienone) as a versatile synthon for upper rim alkoxylation of calixarenes and synthesis of novel triazole-based biscalixarene by 'CuAAC' chemistry
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The spiro rings of calix[4]bis(spirodienone) have been opened up using various bromofunctionalised alcohols employing a novel ipso nucleophilic substitution of tert-butyl groups by alkoxy groups. Additionally, a route has been paved towards the preparation of triazole-linked biscalixarene via the copper(I)-catalysed modern version of classical Huisgen 1,3-dipolar cycloaddition of alkynyl calixarene and azidocalixarene, derived from the above-mentioned bromo-substituted calixarene.
- Thulasi, Sreeja,Savithri, Anupriya,Varma, Ramavarma Luxmi
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experimental part
p. 501 - 508
(2012/06/18)
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- Design, synthesis, and self-assembly behavior of C3-symmetry discotic molecules via click chemistry
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We prepared a series of C3-symmetry discogens with three 1,2,3-triazoles and a central benzene ring by a copper-catalyzed "click reaction" between 1,3,5-triethynylbenzene and 3,4,5-trialkoxybenzyl azides. According to the differential scanning
- Ryu, Mi-Hee,Choi, Jin-Woo,Cho, Byoung-Ki
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scheme or table
p. 1806 - 1810
(2010/07/08)
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- Microporous polyphenylenes with tunable pore size for hydrogen storage
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A series of highly porous polymers with similar BET surface areas of higher than 1000 m2 g-1 but tunable pore ranging from 0.7 nm to 0.9 nm were synthesized through facile ethynyl trimerization reaction to demonstrate the surface pro
- Yuan, Shengwen,Dorney, Brian,White, Desiree,Kirklin, Scott,Zapol, Peter,Yu, Luping,Liu, Di-Jia
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supporting information; experimental part
p. 4547 - 4549
(2010/10/21)
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- Conformational Control of benzyl-o-carboranylbenzene derivatives and molecular encapsulation of acetone in the dynamically formed space of 1,3,5-Tris(2-benzyl-o-carboran-1-yl)benzene
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A 1,3,5-substituted benzene platform has been widely used in the fields of supramolecular chemistry and molecular recognition. Here, we show that 1,3,5-tris(2-benzyl-o-carboran-1-yl)benzene 6 exhibits solvent-dependent conformation in the crystalline stat
- Songkram, Chalermkiat,Ohta, Kiminori,Yamaguchi, Kentaro,Pichierri, Fabio,Endo, Yasuyuki
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scheme or table
p. 11174 - 11183
(2011/02/16)
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- Star-shaped oligothiophenes with unique photophysical properties and nanostructured polymorphs
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Shining star: Star-shaped hexakis(oligothienylethynyl)benzene with C 6 symmetry shows solvatochromic fluorescence with a marked redshift in emission. Furthermore, the star-shaped molecule shows a fairly large two-photon absorption property. Int
- Narita, Tomoyuki,Takase, Masayoshi,Nishinaga, Tohru,Iyoda, Masahiko,Kamada, Kenji,Ohta, Koji
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supporting information; experimental part
p. 12108 - 12113
(2011/02/23)
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- Solvophobic effects in the self-assembly of triangular-shape amphiphilic oligo(phenylene ethynylenes)
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Triangular-shape OPEs, decorated In their periphery with a variable number of hydrophilic and hydrophobic substituants, have been synthesized to evaluate the Influence of the solvent-solute and solute-solute Interactions Involved In their self-association
- Garcia, Fatima,Aparicio, Fatima,Fernandez, Gustavo,Sanchez, Luis
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scheme or table
p. 2748 - 2751
(2009/11/30)
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- Synthesis of a nanocar with organometallic wheels
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A new class of nanovehicles incorporating trans-alkynyl(dppe)2ruthenium-based wheels is reported. A four-wheeled nanocar and a three-wheeled trimer were synthesized for future studies at the single molecule level.
- Vives, Guillaume,Tour, James M.
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scheme or table
p. 1427 - 1430
(2009/06/18)
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- Strong CO2 binding in a water-stable, triazolate-bridged metal-organic framework functionalized with ethylenediamine
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(Figure Presented) Reaction of CuCl2·2H2O with 1,3,5-tris(1H-1,2,3-triazol-5-yl)benzene (H3BTTri) in DMF at 100°C generates the metal-organic framework H3[(Cu 4Cl)3(BTTri)8(DMF)
- Demessence, Aude,D'Alessandro, Deanna M.,Foo, Maw Lin,Long, Jeffrey R.
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supporting information; experimental part
p. 8784 - 8786
(2009/12/04)
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- Cyclopentadienyl ruthenium(II) complexes with bridging alkynylphosphine ligands: Synthesis and electrochemical studies
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The reaction of [CpRuCl-(PPh3)2] (Cp= cyclopentadienyl) and [CpRuCl(dppe)] (dppe=Ph2PCH2CH 2PPh2) with bis-and trisphosphine ligands 1,4-(Ph 2PC= C)2C6H4 (1) and 1,3,5-(Ph 2PC= C)3C6H3 (2), prepared by Ni-catalysed cross-coupling reactions between terminal alkynes and diphenylchlorophosphine, has been investigated. Using metal-directed self-assembly methodologies, two linear bimetallic complexes,[{CpRuCl(PPh 3)}2(μ-dppab)] (3) and[{CpRu(dppe)}2(μ- dppab)](PF6)2 (4), and the mononuclear complex [CpRuCl(PPh3)(η1-dppab)] (6), which contains a dangling arm ligand, were prepared (dppab=1,4-bis[(diphenylphosphino) ethynyl]benzene). Moreover, by using the triphosphine 1,3,5- tris[(diphenylphosphino)ethynyl]benzene (tppab), the trimetallic [{CpRuCl-(PPh3)}3(μ3-tppab)] (5) species was synthesised, which is the first example of a chiral-at-ruthenium complex containing three different stereogenic centres. Besides these open-chain complexes, the neutral cyclic species [{CpRuCl(μdppab)}2] (7) was also obtained under different experimental conditions. The coordination chemistry of such systems towards supramolecular assemblies was tested by reaction of the bimetallic precursor 3 with additional equivalents of ligand 2. Two rigid macrocycles based on cis coordination of dppab to [CpRu-(PPh 3)] were obtained, that is, the dinuclear complex [{CpRu(PPh 3)(mdppab)}2](PF6)2 (8) and the tetranuclear square [{CpRu(PPh3)(mdppab)}3](PF 3)3 (9). The solid-state structures of 7 and 8 have been determined by X-ray diffraction analysis and show a different arrangement of the two parallel dppab ligands. All compounds were characterised by various methods including ESIMS, electrochemistry and by X-band ESR spectroscopy in the case of the electrogenerated paramagnetic species.
- Di Credico, Barbara,De Biani, Fabrizia Fabrizi,Gonsalvi, Luca,Guerri, Annalisa,Ienco, Andrea,Laschi, Franco,Peruzzini, Maurizio,Reginato, Gianna,Rossin, Andrea,Zanello, Piero
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scheme or table
p. 11985 - 11998
(2010/04/28)
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- 1,3,5-Tris(functionalised-phenylethynyl)benzene-metal complexes: Synthetic survey of mesoporous coordination polymers and investigation of their carbonisation
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A series of multicoordinate 1,3,5-tris(functionalised-phenylethynyl) benzenes (1-9) was synthesised, and coordination polymers were constructed from these organic linkers and copper ions in high yields. The carbonisation of the linkers 1-9 afforded a micr
- Kobayashi, Norifumi,Kijima, Masashi
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supporting information; experimental part
p. 1037 - 1045
(2009/05/08)
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