- Synthesis and geometric structure of N, N, N'-tris(Benzoyl)trimesinic acid dihydrazide
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N, N, N'-Tris(benzoyl) trimesinic acid dihydrazide was synthesized from benzoyl hydrazine and trischloride and the structures of N,N,N'- tris(benzoyl) trimesinic acid dihydrazide had been characterized by Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance techniques. The reaction condition was investigated by orthogonal experiment and the optimized reaction condition by orthogonal experiment is molar ratio of benzoyl hydrazine: trischloride 5:1, reaction time 4 h, reaction temperature 70°C, the yield is 65.7 %. SEM showed the particles of N,N,N'-tris(benzoyl)trimesinic acid dihydrazide were not completely regular and the average size of the particles was 3-4 μm. At the same time, the optimized geometric structure of N,N,N'-tris(benzoyl)trimesinic acid dihydrazide was carried out by theoretical calculations using the semiempirical method PM3.
- Cai, Yan-Hua,Zhao, Li-Sha,Ren, Li-Ping,Wang, Feng
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Read Online
- Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms
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Star-shaped conjugated molecules, consisting of a benzene central unit symmetrically trisubstituted with either oxa- or thiadiazole bithiophene groups, were synthesized as promising molecules and building blocks for application in (opto)electronics and electrochromic devices. Their optical (Eg(opt)) as well as electrochemical (Eg(electro)) band gaps depended on the type of the side arm and the number of solubilizing alkyl substituents. Oxadiazole derivatives showed Eg(opt) slightly below 3 eV and by 0.2 eV larger than those determined for thiadiazole-based compounds. The presence of alkyl substituents in the arms additionally lowered the band gap. The obtained compounds were efficient electroluminophores in guest/host-type light-emitting diodes. They also showed a strong tendency to self-organize in monolayers deposited on graphite, as evidenced by scanning tunneling microscopy. The structural studies by X-ray scattering revealed the formation of supramolecular columnar stacks in which the molecules were organized. Differences in macroscopic alignment in the specimen indicated variations in the self-assembly mechanism between the molecules. The compounds as trifunctional monomers were electrochemically polymerized to yield the corresponding polymer network. As shown by UV/Vis-NIR spectroelectrochemical studies, these networks exhibited reversible electrochromic behavior both in the oxidation and in the reduction modes.
- Kotwica, Kamil,Kostyuchenko, Anastasia S.,Data, Przemyslaw,Marszalek, Tomasz,Skorka, Lukasz,Jaroch, Tomasz,Kacka, Sylwia,Zagorska, Malgorzata,Nowakowski, Robert,Monkman, Andrew P.,Fisyuk, Alexander S.,Pisula, Wojciech,Pron, Adam
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Read Online
- Uncommon hexagonal microtubule based gel from a simple trimesic amide
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A small molecule of N,N′,N″-tris(3-methylpyridyl)-trimesic amide was assembled into a novel hexagonal microtube through intermolecular hydrogen bonds, and simultaneously formed a gel system in H2O-THF mixed solvent. Tuning gelator concentration or the preparation method can effectively control the size of the hexagonal tubes. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2008.
- Shi, Naien,Yin, Gui,Li, Hongbian,Han, Min,Xu, Zheng
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- Cobalt Metallogel Interface for Selectively Sensing l -Tryptophan among Essential Amino Acids
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The development of metallogels widens the span of sensing activity as it opens new opportunities to develop chemosensors through metal-ligand interactions. Herein, a new nitrile-substituted 1,3,5-tricarboxamide-based gelator G4 has been fabricated and shows aggregate-induced enhanced emission (AIEE) after gelation in the presence of water. A dimethylformamide (DMF) solution of the gelator shows rapid crystallization, but addition of water to a DMF solution of gelator G4 leads to gelation at room temperature. In addition, gelator G4 was used for the formation of metallogels, and among them, the cobalt metallogel has been found to be effective for sensing l-tryptophan in the gel state through the quenching of AIEE. Interestingly, the gel is also effective in sensing bovine serum albumin protein at the nanomolar level, which contains an l-tryptophan residue. The limit of detection of Co(II)G4 for selective sensing of tryptophan has been found to be 2.4 × 10-8 M. To the best of our knowledge, there have been no reports to date of a metallogel being utilized to discriminate and selectively sense an amino acid and a protein. The gelation properties of the organic gelator molecule and metallogels have been explored through various spectroscopic tools and physicochemical experiments.
- Malviya, Novina,Sonkar, Chanchal,Ganguly, Rakesh,Mukhopadhyay, Suman
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Read Online
- Tuning of Bistability, Thermal Stability of the Metastable States, and Application Prospects in the C3-Symmetric Designs of Multiple Azo(hetero)arenes Systems
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Light-responsive molecular systems with multiple photoswitches in C3-symmetric designs have enormous application potential. The design part of such molecular systems is critical due to its influence in several properties associated with the photoswitches. In order to tune, and in the evaluation of the design–property relationship, we synthesized 18 tripodal systems with variations in the core, linkers, connectivity, and azo(hetero)arene photoswitches. Through extensive spectroscopic and computational studies, we envisaged the factors controlling near-quantitative photoisomerization in both the directions (bistability) and the thermal stability of the metastable states. Furthermore, we also evaluated the impact of designs in obtaining reversible photo-responsive sol-gel phase transitions, solvatochromism, photo- and thermochromism.
- Gupta, Debapriya,Gaur, Ankit Kumar,Kumar, Pravesh,Kumar, Himanshu,Mahadevan, Anjali,Devi, Sudha,Roy, Saonli,Venkataramani, Sugumar
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supporting information
p. 3463 - 3472
(2021/01/21)
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- Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids
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The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.
- Yu, Zhiqun,Yao, Hongmiao,Xu, Qilin,Liu, Jiming,Le, Xingmao,Ren, Minna
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supporting information
p. 685 - 689
(2021/04/09)
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- Instant Photochromism Caused by Radical Formation in Photocatalytic Decarboxylation of Dihydrothiazole Derivative?
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A pair of new enantiomeric compounds, (R)/(S)-1,3,5-benzene-triyl-2,2',2”-tris(4,5-dihydrothiazole-4-carboxylic acid) (H3LRRR and H3LSSS) are synthesized in one step synthetic route with high yield. Instant photochromism has been investigated to elaborate the photocatalytic decarboxylation of the dihydrothiazole derivative by electron paramagnetic resonance spectroscopy (EPR), photoluminescence (PL), FT-IR, high resolution mass spectra, X-ray photoelectron spectroscopy and UV-Vis spectroscopic techniques. The results indicate that the photochromic transformation is originated from the formation of the radical during the photocatalytic decarboxylation of the 4,5-dihydrothiazole-4-carboxylic acid units.
- Xu, Zhen,Malik, Abaid Ullah,Shu, Mouhai,Cui, Yong
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p. 2774 - 2780
(2021/08/09)
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- Citrate plasticizer
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The invention discloses a citrate plasticizer and a preparation method thereof, and the preparation method of citrate comprises the following steps: firstly, citric acid and alcohol react to prepare citric acid triester, and then dianhydride acylation is carried out to prepare carboxyl-containing citric acid triester. After chlorination, the carboxyl-containing citric acid triester and the tris(2-ethoxyl) isocyanurate are subjected to esterification reaction to prepare triester citrate containing the isocyanurate. According to the present invention, the preparation method has characteristics of simple operation, wide raw material source and mild reaction condition, and meets the industrial production, the prepared triester citrate containing isocyanurate has a good plasticizing effect and excellent thermal stability, low-temperature flexibility, solvent extraction resistance, migration resistance and flame retardance, and can be widely applied to plastic rubber plasticizers.
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Paragraph 0061; 0064; 0066; 0069
(2021/05/15)
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- C3 The symmetry contains a chiral ligand H3L of an amide bond. Preparation method and application
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The invention discloses C. 3 Chiral ligand H with symmetric amide bond3 L Relates to the technical field of material chemistry and chiral chemistry. The invention further provides the chiral ligand H. 3 L Preparation method and application thereof. The present invention has the advantage that the chiral ligand H of the present invention is a chiral ligand. 3 The L has a higher C. 3 The symmetric and flexible amide group enables coordination of the lanthanide metal ions with high coordination number and high oxygen affinity to be assembled into a novel structure-structure lanthanide metal chiral porous coordination cage. Moreover, the abundant chiral amide groups and amino acid residues on the ligand framework can be directly introduced into the synthesized lanthanide metal chiral porous coordination cage, thereby being beneficial to generating multiple chiral recognition sites and unique chiral microenvironments which mimic the biological enzyme binding pocket and further realize the purpose of high enantioselectivity separation of a series of chiral small molecule compounds.
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Paragraph 0071-0074
(2021/09/08)
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- Homochiral Dodecanuclear Lanthanide "cage in Cage" for Enantioselective Separation
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It is extremely difficult to anticipate the structure and the stereochemistry of a complex, particularly when the ligand is flexible and the metal node adopts diverse coordination numbers. When trivalent lanthanides (LnIII) and enantiopure amino acid ligands are utilized as building blocks, self-assembly sometimes yields rare chiral polynuclear structures. In this study, an enantiopure carboxyl-functionalized amino acid-based ligand with C3 symmetry reacts with lanthanum cations to give a homochiral porous coordination cage, (Δ/λ)12-PCC-57. The dodecanuclear lanthanide cage has an unprecedented octahedral "cage-in-cage"framework. During the self-assembly, the chirality is transferred from the enantiopure ligand and fixed by the binuclear lanthanide cluster to give 12 metal centers that have either Δor λ homochiral stereochemistry. The cage exhibits excellent enantioselective separation of racemic alcohols, 2,3-dihydroquinazolinones, and multiple commercially available drugs. This finding exhibits a rare example of a multinuclear lanthanide complex with a dual-walled topology and homochirality. The highly ordered self-assembly and self-sorting of flexible amino acids and lanthanides shed light on the chiral transformation between different complicated artificial systems that mimic natural enzymes.
- Zhu, Chengfeng,Tang, Haitong,Yang, Keke,Fang, Yu,Wang, Kun-Yu,Xiao, Zhifeng,Wu, Xiang,Li, Yougui,Powell, Joshua A.,Zhou, Hong-Cai
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supporting information
p. 12560 - 12566
(2021/08/23)
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- Amide pyrazole compound and preparation method and application thereof
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The invention provides an amide pyrazole compound and a preparation method and application thereof. The amide pyrazole compound has a structure as shown in a formula I or II, and R is 5-pyrazolyl or 4-pyrazolyl. An amide structure is combined with pyrazole ligands, a series of amide pyrazole compounds are obtained by designing different coordination angles, coordination numbers and the like, and the amide pyrazole compound has the advantages of rich coordination forms, diversified functions, outstanding performance and the like, and can be applied to the fields of coordination chemistry, organic chemistry, inorganic chemistry, biochemistry, biopharmacy and the like. The preparation method has the advantages of few synthesis steps, simple operation and low production cost, and the yield is75% or above so that the preparation method is suitable for industrial production.
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Paragraph 0048-0054
(2020/09/09)
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- Synthesis of Dendritic Glycoclusters and Their Applications for Supramolecular Gelation and Catalysis
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Glycoclusters with three, four, and six arms of glycosyl triazoles were designed, synthesized, and characterized. The self-assembling properties of these molecules and their catalytic activity as ligands in copper-catalyzed azide and alkyne cycloaddition (CuAAC) reactions were studied. The compounds with a lower number of branches exhibit excellent gelation properties and can function as supramolecular gelators. The resulting gels were characterized using optical microcopy and atomic force microscopy. The glycoconjugates containing six branches showed significant catalytic activity for copper sulfate mediated cycloaddition reactions. In aqueous solutions, 1 mol % of glycoclusters to substrates was efficient at accelerating these reactions. Several trimeric compounds were found to be capable of forming co-gels with the catalytically active hexameric compounds. Using the organogels formed by the glycoconjugates as supramolecular catalysts, efficient catalysis was demonstrated for several CuAAC reactions. The metallogels with CuSO4 were also prepared as gel columns, which can be reused for the cycloaddition reactions several times. These include the preparation of a few glycosyl triazoles and aryl triazoles and isoxazoles. We expect that these sugar-based soft biomaterials will have applications beyond supramolecular catalysis for copper-catalyzed cycloaddition reactions. They may also be useful as ligands or gel matrixes for other metal-ion catalyzed organic reactions.
- Wang, Guijun,Wang, Dan,Bietsch, Jonathan,Chen, Anji,Sharma, Pooja
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p. 16136 - 16156
(2021/01/09)
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- Process for preparing trimesoyl chloride
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The invention belongs to the field of organic synthesis, and particularly relates to a process for preparing trimesoyl chloride. The process comprises the following steps: using trimesic acid and thionyl chloride as raw materials, adding a mixed catalyst, and performing a reflux reaction in a solvent, wherein the mixed catalyst is a mixture of N,N-dimethylformamide, octadecyl trimethyl ammonium bromide and (methoxymethyl)triphenylphosphonium chloride; and after the reaction is completed, performing reduced-pressure distillation to remove the solvent and the thionyl chloride, and performing vacuum distillation to obtain the trimesoyl chloride. The process provided by the invention adopts the mixed catalyst, the mixed catalyst has a good catalytic effect and a high yield, and the synthesizedtrimesoyl chloride has a content of 99.5% or more and a reaction yield of 98% or more; and the solvent and the thionyl chloride can be recycled, so that the costs are saved, and the industrialized production is easy to realize.
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Paragraph 0024-0033
(2019/07/04)
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- Synthetic method for trimesoyl chloride
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The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method for trimesoyl chloride. The method comprises the following steps: performing a reaction on trimesic acid and thionyl chloride under the action of a mixed catalyst, wherein the mixed catalyst is a mixture of N,N-dimethylformamide and octadecyl trimethyl ammonium bromide; and after the reaction iscompleted, performing cooling, and performing recrystallization by using ethyl ether to obtain the trimesoyl chloride. The method provided by the invention has a simple process, adopts the compositecatalyst, avoids addition of a solvent, has simple post-treatment, avoids distillation and other treatment, has low costs and is easy to operate; and the obtained product has a content of 98% or moreand a yield of 92% or more, the economic benefits are good, and the industrialized production is easy to realize.
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Paragraph 0017-0026
(2019/07/04)
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- Double Addition of Alkynyllithium Reagents to Amides/Lactams: A Direct and Flexible Synthesis of 3-Amino-1,4-diynes Bearing an Aza-Quaternary Carbon Center
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An efficient and mild protocol for the direct and flexible synthesis of 3-amino-1,4-diynes bearing an aza-quaternary carbon from tertiary amides and lactams has been established. The one-pot method consists of in situ activation of amides with trifluoromethanesulfonic anhydride, followed by double addition of alkynyllithium reagents at a concentration of 0.5 mol·L-1 in dichloromethane. This constitutes an extension of the method of direct reductive bisalkylation of amides that allows both employing alkynyllithium reagents as the first-addition nucleophiles and incorporating an alkynyl group as the first-introduced group.
- Chen, Hang,Huang, Ying-Hong,Ye, Jian-Liang,Huang, Pei-Qiang
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p. 9270 - 9281
(2019/08/12)
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- Reversibly photoswitchable alkoxy azobenzenes connected benzenetricarboxamide discotic liquid crystals with perpetual long range columnar assembly
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Liquid crystals (LCs) with photoswitchable groups are very interesting owing to their dual applications. In this regard, we report the synthesis of long chain alkoxy azobenzene incorporated benzenetricarboxamides 7a-c based room temperature columnar LCs. Apart from the light induced isomerization in the solution phase, the salient feature of these systems is the reversible photoisomerization even in the bulk state with perpetual columnar self-assembly at room temperature. Based on the observation of mesomorphic textures under polarised optical microscopy (POM) and grazing incidence small/wide angle X-ray scattering (GISAXS/GIWAXS) studies, the columnar assembly was found to be stable upon photoisomerization. However, subtle changes in height profile have been observed in AFM measurements after photoswitching. Interestingly, a temperature dependent change between rectangular and hexagonal mesophases in 7a has been observed. Upon extending the alkoxy chain length, only the hexagonal mesophase was observed. For comparison, the corresponding N-methylated derivative of 7a has also been synthesized. Despite the better photoswitching behaviour, due to the lack of planarity and H-bonding, 8a did not show any columnar mesophase.
- Devi, Sudha,Bala, Indu,Gupta, Santosh Prasad,Kumar, Pravesh,Pal, Santanu Kumar,Venkataramani, Sugumar
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supporting information
p. 1947 - 1954
(2019/02/20)
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- COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE
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Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.
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Paragraph 0095; 00110
(2019/04/09)
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- Protection strategies for directionally-controlled synthesis of previously inaccessible metal-organic polyhedra (MOPs): The cases of carboxylate: The amino-functionalised Rh(ii)-MOPs
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Herein we report that strategic use of protecting groups in coordination reactions enables directional inhibition that leads to synthesis of highly functionalised metal-organic polyhedra (MOPs), rather than of the extended coordination networks. Using this approach, we functionalised two new porous cuboctahedral Rh(ii)-based MOPs with 24 peripheral carboxylic acid groups or 24 peripheral amino groups.
- Albalad, Jorge,Carné-Sánchez, Arnau,Grancha, Thais,Hernández-López, Laura,Maspoch, Daniel
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supporting information
p. 12785 - 12788
(2019/11/05)
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- Exploiting Peptidomimetics to Synthesize Compounds That Activate Ryanodine Receptor Calcium Release Channels
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Ryanodine receptor (RyR) Ca2+-release channels are essential for contraction in skeletal and cardiac muscle and are prime targets for modification of contraction in disorders that affect either the skeletal or heart musculature. We designed and synthesized a number of compounds with structures based on a naturally occurring peptide (A peptides) that modifies the activity of RyRs. In total, 34 compounds belonging to eight different classes were prepared. The compounds were screened for their ability to enhance Ca2+ release from isolated cardiac sarcoplasmic reticulum (SR) vesicles, with 25 displaying enhanced Ca2+ release. Competition studies with the parent peptides indicated that the synthetic compounds act at a competing site. The activity of the most effective of the compounds, BIT 180, was further explored using Ca2+ release from skeletal SR vesicles and contraction in intact skeletal muscle fibers. The compounds did not alter tension in intact fibers, indicating that (as expected) they are not membrane permeable, but importantly, that they are not toxic to the intact cells. Proof in principal that the compounds would be effective in intact muscle fibers if rendered membrane permeable was obtained with a structurally related membrane-permeable scorpion toxin (imperatoxin A), which was found to enhance contraction.
- Robinson, Ken,Easton, Christopher J.,Dulhunty, Angela F.,Casarotto, Marco G.
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p. 1957 - 1971
(2018/09/11)
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- Aromatic Esters, Carbinols, and Derivatives Thereof with Perfluorohexyl Residues as Alternatives to Perfluoroalkanecarboxylic and -sulfonic Acids
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Four perfluorohexyl carbinols have been prepared from the corresponding Grignard reagent and benzaldehyde, terephthalaldehyde, isophthalaldehyde, and trimesaldehyde. The corresponding secondary alcohols were then transformed by alkylation and acylation reactions to form a total of 14 ethers (methyl, ethyl, propyl, and n-hexyl ethers) and esters (acetyl and 2-ethylhexanoyl), respectively. Furthermore, 11 perfluoroalkyl carboxylates were prepared from aromatic, heteroaromatic, and aliphatic mono-, di-, tri-, and tetracarboxylic acids and tridecafluorooctanol. The wettability of all 29 materials was investigated by the water contact angle measurements of thin films on glass surfaces. In up to six cases, contact angles greater than 130° were observed, which indicates that the products might be suitable candidates for the impregnation of surfaces. With their relatively short perfluoroalkyl side-chains and therefore low bioaccumulativity, the target compounds might be beneficial alternatives to established products.
- Alpers, Torben,Muesmann, Thomas W. T.,Temme, Oliver,Christoffers, Jens
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p. 609 - 617
(2017/02/05)
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- A smart organic gel template as metal cation and inorganic anion sensor
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A carboxamide based molecule has shown unique gelation property in an aqueous mixture of DMF or DMSO. The gel itself has shown aggregation-induced fluorescence enhanced emission (AIEE), which can be utilized effectively in sensing ferrous and ferric ions as both of them switch off the fluorescence completely. An investigation by IR spectroscopy reveals an enhanced π interaction of nitrile group with the iron center and this could be the possible reason behind the complete quenching of AIEE. This molecule was further investigated for the formation of metallogels for a wide array of cations, which in turn can act in tandem to behave as a dynamic array to detect several anions by either switching off or switching on the emission property of the metallogels.
- Malviya, Novina,Das, Mriganka,Mandal, Poulami,Mukhopadhyay, Suman
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p. 6243 - 6249
(2017/10/03)
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- CLEAN PROCESS FOR PREPARING CHLOROFORMYL-SUBSTITUTED BENZENE
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Clean process for preparing a chloroformyl-substituted benzene by oxidation of a tail gas hydrogen chloride from a chlorination reaction and a chloroacylation reaction and recycling of the resulting oxidation product chlorine gas into the chlorination reaction. The present invention provides a clean process for preparing a polymer-grade chloroformyl-substituted benzene.
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Paragraph 0126; 0152; 0163
(2017/12/17)
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- Aromatic polycarboxylic acid method of manufacturing multi-acyl chloride
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The invention provides a making method for aromatic polycarboxylic acid polyacylchloride, and the method comprises the following procedures: using acylchloride catalyst of chloride or oxide containing Fe or Zn, reacting aromatic polycarboxylic containing sodium under 150 ppm with (trichloromethyl) benzol compound, and obtaining reaction product; and distilling and purifying the reaction product.
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Paragraph 0111; 0112
(2017/03/17)
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- Synthesis and Application of C2 and C3 Symmetric (R)-Phenylglycinol-Derived Chiral Stationary Phases
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A C3 symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral stationary phase (CSP) and three C2 symmetric (R)-phenylglycinol CSPs were newly synthesized using o-, m-, and p-phthaloyl dichlorides.
- Yu, Jeongjae,Ryoo, Dong Hyun,Lee, Jung Mi,Ryoo, Jae Jeong
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p. 186 - 191
(2016/02/26)
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- A organic adsorption the benzene is special poroid material and its preparation method
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The invention relates to the technical field of porous materials and preparation thereof, and in particular relates to a pure organic porous material for especially absorbing benzene and a preparation method of the porous material. The pure organic porous material for especially absorbing benzene and the preparation method begin with acyl chloride, furthermore amide containing pyridine groups are synthesized, and finally the pure organic porous material for especially absorbing benzene is prepared; the synthesis route is simple, the operation is convenient, and the yield is high.
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Paragraph 0026; 0027
(2017/03/22)
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- Insights into the formation of chiral second sphere coordination complexes with aromatic tris amines: combined single crystal X-ray crystallography and molecular modeling analyses
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A family of isostructural, chiral supramolecular networks have been obtained in the solid state by exploiting second sphere coordination interactions in the self-assembly of achiral tris amines L1 and L2 with tetrahalometallate and halide ions. Quantum-Mechanical (QM) calculations specific for solid phases provided additional insights into the intramolecular and packing interactions which determine chirality, pointing to a direct effect of the methyl groups of the central benzene ring.
- Yu, Hong-Cui,Li, Lei,Gao, Ji,Tong, Jian,Zheng, Wenxu,Cametti, Massimo,Famulari, Antonino,Meille, Stefano Valdo,Guo, Fang,Martí-Rujas, Javier
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supporting information
p. 15960 - 15965
(2015/09/15)
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- Luminescent columnar liquid crystals based on 1,3,4-oxadiazole
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In this study five new compounds, derivatives of 1,3,4-oxadiazole, were synthesized in order to achieve mesomorphic behavior and luminescence. Different types of aliphatic chains were used in order to investigate the influence of alkoxide groups in mesomorphic behavior. All of the compounds showed high thermal stability and strong blue photoluminescence in solution and in solid films. Furthermore, compounds 10a-d presented hexagonal columnar mesomorphism, which was characterized by polarizing optical microscopy and X-ray diffraction, and strong π-stacking was observed. Notably, for two compounds (10c,d), the liquid crystal properties were preserved on cooling from the isotropic state to room temperature. These characteristics make these materials good candidates for application in organic electronics.
- Girotto, Edivandro,Eccher, Juliana,Vieira, André A.,Bechtold, Ivan H.,Gallardo, Hugo
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supporting information
p. 3355 - 3360
(2014/05/06)
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- New core-pyrene π structure organophotocatalysts usable as highly efficient photoinitiators
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Eleven di- and trifunctional compounds based on a core-pyrene π structure (Co-Py) were synthesized and investigated for the formation of free radicals. The application of two- and three-component photoinitiating systems (different Co-Pys with the addition of iodonium or sulfonium salts, alkyl halide or amine) was investigated in detail for cationic and radical photopolymerization reactions under near-UV-vis light. The proposed compounds can behave as new photocatalysts. Successful results in terms of rates of polymerization and final conversions were obtained. The strong MO coupling between the six different cores and the pyrene moiety was studied by DFT calculations. The different chemical intermediates are characterized by ESR and laser flash photolysis experiments. The mechanisms involved in the initiation step are discussed, and relationships between the core structure, the Co-Py absorption property, and the polymerization ability are tentatively proposed.
- Telitel, Sofia,Dumur, Frederic,Faury, Thomas,Graff, Bernadette,Tehfe, Mohamad-Ali,Gigmes, Didier,Fouassier, Jean-Pierre,Lalevee, Jacques
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supporting information
p. 877 - 890
(2013/07/05)
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- A microporous hydrogen-bonded organic framework: Exceptional stability and highly selective adsorption of gas and liquid
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An extremely stable hydrogen-bonded organic framework, HOF-8, was fabricated. HOF-8 is not only thermally stable but also stable in water and common organic solvents. More interestingly, desolvated HOF-8 exhibits high CO2 adsorption as well as highly selective CO2 and C 6H6 adsorption at ambient temperature.
- Luo, Xu-Zhong,Jia, Xin-Jian,Deng, Ji-Hua,Zhong, Jin-Lian,Liu, Hui-Jin,Wang, Ke-Jun,Zhong, Di-Chang
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supporting information
p. 11684 - 11687
(2013/09/02)
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- Single-walled polytetrazolate metal-organic channels with high density of open nitrogen-donor sites and gas uptake
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The self-assembly between zinc dimer and 1,3,5-tris(2H-tetrazol-5-yl) benzene (H3BTT), promoted by a urea derivative, leads to a highly porous 3D framework with a large percentage (67%) of N-donor sites unused for bonding with metals. The material exhibits high gas storage capacity (ca. 1.89 wt % H2 at 77 K and 1 atm; 98 cm3/g CO2 at 273 K and 1 atm), even in the absence of open metal sites. The high percentage of open N-donor sites, coupled with the low framework density resulting from single-walled channels, is believed to contribute to the high uptake capacity.
- Lin, Qipu,Wu, Tao,Zheng, Shou-Tian,Bu, Xianhui,Feng, Pingyun
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supporting information; experimental part
p. 784 - 787
(2012/03/07)
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- Metal-organic polyhedra containing 36 and 24 folds of amide groups for selective luminescent recognition of natural disaccharides
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An octa-nuclear bicoronal Ce-based triangular prism and tetra-nuclear molecular tetrahedron containing 36 and 24 folds amides within their main backbones were achieved and structurally characterized for the selective luminescent recognition of lactose and sucrose, respectively, over other related natural mono- and disaccharides.
- Jiao, Yang,Zhang, Jing,Zhang, Lejie,Lin, Zhihua,He, Cheng,Duan, Chunying
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supporting information; experimental part
p. 6022 - 6024
(2012/07/01)
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- Hetero bi-paddle-wheel coordination networks: A new synthetic route to Rh-containing metal - Organic frameworks
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We have successfully synthesized rhodium-containing MOFs with 1:1 abundance ratios of paddle-wheel units of Rh2 and Cu2/Zn 2, i.e., [Rh2M2(1,4-bdc)2] ·nSolvent (M = Cu: RhCu-DMF, RhCu-EtOH; M = Zn: RhZn-DMF; 1,4- bdc: 1,4-benzenedicarboxylate) by a novel synthetic method involving assembly of discrete paddle-wheel dirhodium(II) tetra(1,4-benzenedicarboxylate) with Cu 2+ or Zn2+ ions. The diffraction patterns of these complexes were very similar to the predicted and experimental XRPD patterns reported for [Cu2(1,4-bdc)2]. This result indicates that this method enables the incorporation of coordinatively unsaturated noble-metal sites for the many reported MOFs with multi-carboxy ligands and paddle-wheel nodes.
- Matsunaga, Satoshi,Hasada, Ken-Ichi,Sugiura, Kenji,Kitamura, Naoki,Kudo, Yuri,Endo, Nanako,Mori, Wasuke
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supporting information; scheme or table
p. 433 - 438
(2012/06/16)
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- Holographic investigations of azobenzene-containing low-molecular-weight compounds in pure materials and binary blends with polystyrene
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This paper reports on the synthesis and the thermal and optical properties of photochromic low-molecular-weight compounds, especially with respect to the formation of holographic volume gratings in the pure materials and in binary blends with polystyrene. Its aim is to provide a basic understanding of the holographic response with regard to the molecular structure, and thus to show a way to obtain suitable rewritable materials with high sensitivity for holographic data storage. The photoactive low-molecular-weight compounds consist of a central core with three or four azobenzene-based arms attached through esterification. Four different cores were investigated that influence the glass transition temperature and the glass-forming properties. Additional structural variations were introduced by the polar terminal substituent at the azobenzene chromophore to fine-tune the optical properties and the holographic response. Films of the neat compounds were investigated in holographic experiments, especially with regard to the material sensitivity. In binary blends of the low-molecular-weight compounds with polystyrene, the influence of a polymer matrix on the behavior in holographic experiments was studied. The most promising material combination was also investigated at elevated temperatures, at which the holographic recording sensitivity is even higher. Fast holographic response: The formation of volume gratings in photochromic low-molecular-weight compounds is investigated. The compounds consist of a central core with azobenzene-based arms attached through esterification (see image). Films of the neat compounds and binary blends of the low-molecular-weight compounds with polystyrene are investigated in holographic experiments.
- Audorff, Hubert,Walker, Roland,Kador, Lothar,Schmidt, Hans-Werner
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experimental part
p. 12722 - 12728
(2011/12/04)
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- Synthesis and structure of a bowl-like molecule by threefold metathesis reactions
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A bowl-like molecule was designed and efficiently synthesized by threefold metathesis reactions, and its structure was determined by NMR, MALDI-TOF MS spectrum, and X-ray crystallographic analysis.
- Cao, Jing,Song, Zhi-Ping,Zhu, Xiao-Zhang,Chen, Chuan-Feng
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experimental part
p. 3112 - 3115
(2010/07/18)
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- A convenient one-pot synthesis of arene-centered tris(thiazoline) compounds
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A simple and practical one-pot synthesis of novel enantiopure tris(thiazoline) compounds was documented. The desired products were obtained in moderate to good yields through three steps from commercially available 1,3, 5-benzenetricarboxylic acid or 2, 4, 6-pyridinetricarboxylic acid, and chiral amino alcohols. Only one column chromatographic purification was needed for the three steps.
- Lu, Xuhong,Qi, Qingqing,Xiao, Yumei,Li, Nan,Fu, Bin
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experimental part
p. 1031 - 1039
(2009/10/04)
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- SOLUBLE DIAZOALKANE PRECURSORS
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The present invention relates to compounds useful in the preparation of diazoalkanes in general (such as diazomethane, diazoethane, diazopropane, diazobutane and homologues) and to diazomethane (CH2=N=N) in particular. The compounds chosen as the diazomethane source according to the invention also have the advantage of being water soluble. They are capable of being decomposed to diazomethane or another diazoalkane (which is allowed to bubble out of the vessel to another vessel containing a solution of reactant) and are converted to by-products that are also water-soluble.
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Page/Page column 16
(2008/06/13)
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- Tricarbamate of 1,3,5-triaminobenzene via Curtius rearrangement of trimesic acid and subsequent nitration
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The triethyl tricarbamate of 1,3,5-triaminobenzene was prepared from trimesic acid in five steps with 70% overall yield. The tricarbamate underwent nitration to give the mono-, di-, or trinitro analogs in excellent yield. Copyright Taylor & Francis Group, LLC.
- Davis, Matthew C.
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p. 1457 - 1462
(2008/02/02)
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- C3-Symmetric, amino acid based organogelators and thickeners: a systematic study of structure-property relations
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A class of C3-symmetric amino acid based organogelators and thickeners featuring a rigid core have been developed. Structural variation yielded a number of compounds, the aggregation behaviour and resulting aggregates and gels of which were studied by FTIR spectroscopy, dropping ball measurements, differential scanning calorimetry and transmission electron microscopy. These studies showed that the nature of the core unit, the type of hydrogen-bonding units and the applied amino acids have a strong influence on the interactions, resulting in large differences in aggregation properties, thermal stability and morphology between the various compounds. The results provide a basis for a better understanding of the relation between aggregate/gel properties and molecular structure. The structural variation available for these compounds allows fine-tuning of the gelators with respect to aggregation behaviour and gel properties.
- de Loos, Maaike,van Esch, Jan H.,Kellogg, Richard M.,Feringa, Ben L.
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p. 7285 - 7301
(2008/02/05)
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- Safer conditions for the Curtius rearrangement of 1,3,5- benzenetricarboxylic acid
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A rapid method to prepare 1,3,5-triaminobenzene and its derivatives is the tris-Curtius rearrangment of 1,3,5-benzenetricarboxylic acid. The hazards associated with the acyl azide route are minimized by using 1,2-dichloroethane as solvent. A second method that avoids acyl azide preparation uses diphenylphosphoryl azide to yield the tricarbamate in one step. Copyright Taylor & Francis Group, LLC.
- Davis, Matthew C.
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p. 3519 - 3528
(2008/03/13)
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- Highly enantioselective borane reduction of prochiral ketones catalyzed by C3-symmetric tripodal β-hydroxy amides
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The asymmetric borane reduction of prochiral ketones with a series of easily constructed chiral C3-symmetric tripodal tris(β- hydroxyamide) ligands was investigated. The borane complex of chiral ligand 1,1′,″,-(1,3,5-benzenetricarbonyl)-tris[(2S)-α, α-diphenyl-2-pyrrolidinemethanol] (1h) was found to be an efficient catalyst in asymmetric borane reduction of prochiral ketones and excellent enantioselectivities were obtained with both electron-deficient and electron-rich prochiral ketones (up to 97% ee). Georg Thieme Verlag Stuttgart.
- Fang, Tao,Xu, Jiaxi,Du, Da-Ming
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p. 1559 - 1563
(2007/10/03)
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- Molecular parameters and mesomorphism of discotic polysubstituted benzene derivatives
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The previously developed approach to prediction of columnar and nematic mesophases for compounds with disc-shaped molecules was applied to low-molecular-weight polysubstituted benzene derivatives. The molecular parameters were calculated for 39 new compounds: derivatives of 1,3,5-tri(4-hydroxybenzoyloxy)benzene, 1,3,5-tri(4-cyclohexylbenzoyloxy)benzene, 1,3,5-tri(4-hydroxyphenylcarboxy)benzene, 1,2,3-tri(4-cyclohexylbenzoyloxy) benzene, etc. The prediction results were checked by the synthesis of certain compounds from the test sample and examination of their mesomorphic behavior. The prediction of the mesomorphism is negative for only three of the 39 compounds considered. The majority of the molecules under consideration tend to form columnar supramolecular packings, and the capability to form a nematic phase is predicted for only eight compounds. For a number of structures, the capability and incapability to form a nematic phase are equally probable. Synthesis and examination of the mesomorphic behavior of seven repesentatives of the series considered showed good agreement with the prediction results. 1,3,5-Tri(4-heptyloxybenzoyloxy)benzene, 1,3,5-tri(4-cyclohexylbenzoyloxy) benzene, 1,3,5-tri(4-nonyloxyphenylcarboxy)-benzene, and 1,2,3-tri(4- cyclohexylbenzoyloxy)benzene pass into the liquid crystal state forming mainly columnar supramolecular packings. 1,3,5-Tri(4-octyloxybenzoyloxy)benzene and 1,3,5-tri(4-nonyloxybenzoyloxy)benzene melt at 55 and 48°C, respectively, without forming a mesophase, which is also well consistent with the prediction results. Pleiades Publishing, Inc., 2006.
- Akopova,Frolova,Kotovich
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p. 258 - 264
(2008/02/08)
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- Synthesis of C3-symmetric tris(β-hydroxy amide) ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aldehydes
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(Chemical Equation Presented) A series of new chiral C3- symmetric tris(β-hydroxy amide) ligands have been synthesized via the reaction of 1,3,5-benzenetricarboxylic chloride and optically pure amino alcohols (up to 96% yield). The asymmetric catalytic alkynylation of aldehydes with these new C3-symmetric chiral tris(β-hydroxy amide) ligands and Ti (OiPr)4 was investigated. Ligand 4c synthesized from (1R,2S)-(-)-2-amino-1,2-diphenylethanol is effective for the enantioselective alkynylation of various aldehydes, and high enantioselectivity was obtained with aromatic aldehydes and α,β-unsaturated aldehyde (up to 92% ee).
- Fang, Tao,Du, Da-Ming,Lu, Shao-Feng,Xu, Jiaxi
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p. 2081 - 2084
(2007/10/03)
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- Gelling agents
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The invention relates to a novel class of gelling agents, to a process of preparing said agents, to the use of said agents to prepare gels, and to the gels thus obtained. A gelling agent or thickener according to the invention comprises a rigid core which is functionalized with three amino acid ester or amide groups by means of an amide or urea linkage. It may be used to gelate or thicken numerous solvents.
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Page/Page column 8
(2008/06/13)
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- Synthesis of novel discotic mesogen containing electron-transportable oxadiazole moiety
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We synthesized and characterized a novel discotic liquid crystalline material (THOB) composed of 1,3,5-tri-substituted benzene core and 2-(4-hexyloxyphenyl)-oxadiazol-5-yl arms. Chemical structure of THOB was characterized using 1H-NMR and mass spectroscopy and its thermal behavior was determined using DSC and polarized optical microscopy. THOB showed narrow mesophase region at around 128°C and exhibited nematic-like texture.
- Kim, Bong Gi,Kim, Sehoon,Park, Soo Young
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p. 391 - 394
(2007/10/03)
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- A new prearranged tripodant ligand N,N′,N″-trimethyl-N,N′,N″-tris(3-pyridyl)-1,3, 5-benzene tricarboxamide is easily obtained via the N-methyl amide effect
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The N-methyl amide cis generating effect has been utilised to create a new prearranged tripodant ligand in two synthetic steps from benzene-1,3,5-tricarboxylic acid. Crystals of the ligand itself and of complexes with metal salts such as silver(I) triflate, copper(I) and copper(II) chloride and ruthenium(II) chloride have been prepared and the crystal structures solved by analysis of X-ray diffraction data.
- Jorgensen, Mikkel,Krebs, Frederik C.
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p. 4717 - 4720
(2007/10/03)
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- Sugar recognition by C3-symmetric oxazoline hosts
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C3-Symmetric tris(oxazoline) derivatives (2S,2R) were designed to complex sugars and alcohols in nonpolar organic solvent through complementary intermolecular hydrogen-bonding interactions. 1H NMR titration demonstrated that the C3-symmetric hosts were capable of anomer-selective recognition for n-octyl-D-glucopyranoside. 1H NMR data revealed intermolecular hydrogen bonds between 2S and glucopyranosides.
- Kim, Hae-Jo,Kim, Yeon-Hwan,Hong, Jong-In
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p. 5049 - 5052
(2007/10/03)
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- Benzocyclobutenones and polymers derived therefrom
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The invention disclosed relates to novel functionalized benzocyclobutenones of structural formula I STR1 wherein R is NH2, reactive NH2 derivatives including acids, acid chlorides, amides and diazonium salts, OH, CN, NO2, H, I, F Br, Cl, mercapto and deuterium. Also disclosed are polymer compositions comprising thermal reaction products of the benzocyclobutenones of formula I and either a polyol or a polyamine.
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- Branched non-covalent complexes between carboxylic acids and two tris(amidines)
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Carboxylic acids and two tris(amidine) bases formed branched 3:1 complexes with high solubility in chlorinated and aromatic solvents, particularly when aromatic carboxylic acids with suitable solubilising substituents were used. Whereas N,N′-diethylamidine complexes 10 proved to be difficult to isolate, the respective imidazoline complexes 14 were easily purified by crystallisation. Association constants were determined for model bis(imidazoline) complexes to be about 103 dm3 mol-1 in the competitive solvent mixture CDCl3-CD3OD (97:3).
- Kraft, Arno
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p. 705 - 714
(2007/10/03)
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- Synthesis of Azapolycyclic Systems Based on the Indolizino[3,4-b]quinoline Skeleton - A Diastereoselective Entry to Potential Oligodentate Artificial Receptors
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A convenient diastereoselective synthetic route to the molecular tweezer bis(indolizino[3,4-b]quinolyl)methane 9 and the rigid indolizino[7′,8′:2,3]quinolino[8,7-h]indolizino[8,7-b]quinolines 14, 15 as potential receptor molecules has been developed, involving double imine condensation followed by Lewis acid catalyzed biscyclization of prolinal-derived bis-(imines) 8 and 13, respectively. Whereas the use of SnCl4 leads to the formation of the planar polycycle 15, the corresponding concave product 14 is formed in the presence of EtAlCl2. Both compounds 14, 15, as well as tweezer 9 have been characterized by X-ray crystal-structure analysis. Although tris(imines) 20, 24 derived from 1,3,5-triaminobenzene (18) and tris(4-aminophenyl)amine (23) could be obtained similarly by molecular sieve-catalyzed condensation, the corresponding triscyclization could not be achieved. However, by attaching preformed indolizino[3,4-b]quinoline subunits 25 and 31 to an aromatic core, the bidentate receptors 30, 33 and the tentacle molecule 28 were accessible.
- Temme, Oliver,Dickner, Tim,Laschat, Sabine,Froehlich, Roland,Kotila, Sirpa,Bergander, Klaus
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p. 651 - 659
(2007/10/03)
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