- Supramolecular Metallacycles and Their Binding of Fullerenes
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The synthesis of a new triaminoguanidinium-based ligand with three tris-chelating [NNO]-binding pockets and C3 symmetry is described. The reaction of tris-(2-pyridinylene-N-oxide)triaminoguanidinium salts with zinc(II) formate leads to the formation of cyclic supramolecular coordination compounds which in solution bind fullerenes in their spherical cavities. The rapid encapsulation of C60 can be observed by NMR spectroscopy and single-crystal X-ray diffraction and is verified using computation.
- Ehnbom, Andreas,G?b, Christian R.,Oppel, Iris M.,Sturm, Lisa,Tobe, Yoshito
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- Dynamic and static excimer: A versatile platform for single component white-light emission and chelation-enhanced fluorescence
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The present study demonstrates the tuning of iconic optical features of pyrene through its judicious assembly with a C3-symmetric triaminoguanidinium ion, leading to the development of a unique multifunctional luminescent material PYTG. By fine tuning the concentration and the external stimuli, such as temperature, the addition of analytes led to a dramatic change in the fluorescence of PYTG, providing an excellent platform for the exploration of the dynamic and static excimer formation. Recently, white-light-emitting molecular probes have received considerable attention from the scientific community due to their great potentials in display devices. Tripodal PYTG was employed as a pure white-light emitter consisting of blue emission from monomers and orange emission from excimers both in solution and thin film with Commission Internationale de l'Eclairage (CIE) coordinates of (0.33, 0.34) and (0.33, 0.38), respectively. The formation of a dynamic excimer along with monomer fluorescence at higher concentrations of PYTG led to tunable emission. Additionally, the rich electronic properties of PYTG allowed efficient detection of trivalent metal ions by turn-on fluorescence and colorimetric sensing of fluoride ions. PYTG selectively detected Fe3+ and Al3+ with nanomolar sensitivity in a semi-aqueous solution via a chelation-enhanced fluorescence response in the orange-red region (λem = 588 nm) by static excimer formation. The 'on-off' fluorescence switching by the consecutive addition of trivalent cations and a chelating ligand EDTA makes PYTG a promising fluorescent molecular switch. A simple and cost-effective strategy, leading to the development of a versatile fluorescent probe and an in-depth exploration of the structure-property relationship as delineated in the present manuscript, will pave the way for the emergence of novel task-specific molecular optical materials.
- Kumar, Virendra,Sk, Bahadur,Kundu, Subhankar,Patra, Abhijit
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- A novel sensitive turn-on fluorescent Zn2+ chemosensor based on an easy to prepare C 3-symmetric schiff-base derivative in 100% aqueous solution
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A C3-symmetric Schiff-base example of the new simple, low cost, highly water soluble, and sensitive turn-on fluorescent Zn2+ chemosensor is described. The sensor was successfully applied to the detection of intracellular Zn2+. Moreover, the sensor could also serve as a potential recyclable component in sensing materials. Notably, the color change is so obvious that all of the recycling process can be seen clearly by the naked eye.
- Zhou, Ying,Li, Zhan-Xian,Zang, Shuang-Quan,Zhu, Yan-Yan,Zhang, Hong-Yan,Hou, Hong-Wei,Mak, Thomas C. W.
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- Preparation and characterization of bis(guanidinium) and bis(aminotetrazolium)dodecahydroborate salts: Green high energy nitrogen and boron rich compounds
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This paper describes the syntheses, crystallization, characterization and energetic properties (calorimetry) of closo-dodecahydroborate salts with guanidinium and aminotetrazolium based cations. The salts were readily produced in good yields by metathesis (ion exchange) reactions depending on the water solubility of the dodecahydroborate salts. Water insoluble salts can be synthesized from the potassium or sodium salts by a simple metathesis reaction with the corresponding halide of the desired organic cation. Water soluble salts can be prepared via two consecutive metathesis reactions: the halide is first converted to the corresponding sulfate, which is reacted in turn with barium dodecahydroborate, yielding the water soluble organic closo(B12H12)2? salt and the insoluble BaSO4. The product salt is conveniently isolated by water evaporation. The aminotetrazolium salt 12d gives nice crystals when recrystallized from DMF and NMP but incorporate solvent. Guanidinium salt 15a recrystallizes from nicely from water as a monohydrate. Thermogravimetric analyses established the thermal stabilities of these compounds. The enthalpies of combustion of representative salts were determined using a constant volume bomb calorimetry. The data shows that these salts possess relatively high heats of combustion (ΔUc, ca. 35 kJ·g?1), and have the potential to serve as green high-energy materials.
- Sharon, Pessia,Afri, Michal,Mitlin, Sergey,Gottlieb, Levi,Schmerling, Bruria,Grinstein, Dan,Welner, Shmuel,Frimer, Aryeh A.
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- A knot-linker planarity control strategy for constructing highly crystalline cationic covalent organic frameworks: Decoding the effect of crystallinity on adsorption performance
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Ionic covalent organic frameworks (iCOFs), a subclass of COFs, offer a functional platform for diverse applications. However, strong charge repulsion between adjacent layers often leads to low-crystalline iCOFs. Herein, we report a knot-linker planarity control strategy to synthesize a highly crystalline iCOF with C3-symmetric cationic units. More planarity of building blocks gives higher crystallinity of iCOFs, leading to a larger surface area and more exposed binding sites of iCOFs. The highly crystalline iCOF in turn gives larger uptake capacity and faster kinetics than the low-crystalline iCOF and the non-crystalline iCOF, uncovering the significance of crystallinity for the removal of pollutants. The prepared highly crystalline TFPT-TGCl-iCOF exhibits larger saturation sorption capacity (893 mg g-1) than previous adsorbents for 2,4-dichlorophenol. The developed strategy provides a new way to construct highly crystalline iCOFs with C3 symmetric-type cationic sites for various applications. This journal is
- Da, Hong-Ju,Qian, Hai-Long,Yan, Xiu-Ping,Yang, Cheng-Xiong
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- Prostate cancer biomarker citrate detection using triaminoguanidinium carbon dots, its applications in live cells and human urine samples
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Citrate is a tricarboxylate, plays vital role in prostate cancer (PC) and the level of citrate is an indicator for PC identification. Herein, triaminoguanidine carbon dots (TAG-CDs) prepared by one step hydrothermal method and used as a citrate receptor. Notably the TAG-CDs without alkaline treatment were highly fluorescent at pH 7 with high quantum yield (11.3%). TAG-CDs were characterized through TEM, XRD, FT-IR, UV–vis and spectrofluorimetry. It is noted that the average size was of 2.8 nm, the presence of highly disordered carbon, retain the functionality of TAG. The absorbance maxima obtained at 294 nm and good emitting response observed at 396 nm. The Y-aromaticity of receptor guanidinium moiety acts as Lewis acid and have peculiar interaction with Lewis base citrate via electrostatic interaction and also protons in the TAG participate hydrogen bonds with citrate, which causes quenching of TAG-CDs. From the obtained linear quenching equation the LOD was found to be 4 nM. The probe expressed high selectivity, high interference tolerance (500 – fold), fast response in 15 mins and good biocompatible. Finally, TAG-CDs utilized for the intracellular imaging of citrate in live MCF-7 cells, it showed good cytotoxicity and delivered contrast images in presence, absence of citrate. TAG-CDs detected the citrate level in human urine samples, the obtained results are validated with HPLC method.
- Rajalakshmi, Kanagaraj,Deng, Tongtong,Muthusamy, Selvaraj,Xie, Meng,Xie, Jimin,Lee, Kang-Bong,Xu, Yuanguo
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- A: C 3-symmetric twisted organic salt as an efficient mechano-/thermo-responsive molecule: A reusable and sensitive fluorescent thermometer
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C3-Symmetric triaminoguanidinium chloride is condensed with N-pentylphenothiazine carboxaldehyde to realise a thermally stable twisted organic salt on a gram scale. It appears as a nonmetallic economic salt having an integrated propeller shape with three tub-like cores and displays efficient reversible mechano- and thermo-fluorochromic behaviour. Unlike previous reports, the designed fluorescent, colorimetric thermometer works over a higher temperature range of 130-170 °C with five distinct colour variations.
- Prusti, Banchhanidhi,Samanta, Pralok K.,English, Niall J.,Chakravarty, Manab
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supporting information
p. 12321 - 12324
(2021/11/30)
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- Alkaline earth metal salts of 3,6-bis-nitroguanyl-1,2,4,5-tetrazine: Promising perchlorate-free environmentally friendly pyrotechnic components
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Alkaline earth metal salts (magnesium, 2; calcium, 3; strontium, 4; barium, 5) with nitrogen-rich 3,6-bis-nitroguanyl-1,2,4,5-tetrazine anion (DNGTz2?) were prepared and characterized by elemental analysis, infrared, and multinuclear NMR spectroscopy. All new compounds were further characterized by single-crystal X-ray diffraction measurements. Full analysis of the crystal structures and graph sets of hydrogen bonds were conducted out. The results revealed a large-scale conjugation effect of DNGTz anion in all four salts and a middle to high densities ranging from 1.751 (2) to 2.296 (5)?g·cm?3. Both 3 and 4 were one-dimensional coordination polymers and show zig-zag chain, whereas 5 crystalized in a two-dimensional sql topological network. Differential scanning calorimetry (DSC) and thermogravimetric (TG) analysis revealed the good thermal stability of all the new salts. Meanwhile, their specific heat capacities are in inverse proportion to atomic number of the metal cations. The constant-volume combustion energy of 2–5 was determined experimentally, and the standard molar enthalpy of formation was backcalculated to evaluate their energetic performance. Impact sensitivity test disclosed that all the four metal salts were insensitive towards impact with a value higher than 40 J. Flame burning test supports their potential application as the environmentally friendly perchlorate-free pyrotechnic components.
- Chen, Xiang,Chen, Yuankai,Guo, Zhaoqi,Hu, Yongpeng,Ma, Haixia,Wang, Shenghui,Zhang, Cong
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- Constructing a 3D-layered energetic metal-organic framework with the strong stacking interactions of hydrogen-bridged rings: The way to an insensitive high energy complex
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Energetic metal-organic frameworks (EMOFs) have drawn considerable attention due to their good energetic performances and acceptable sensitivity. Among these, 3D EMOFs show good thermal stability and mechanical insensitivity. Nevertheless, most of the 3D EMOFs have porous structures and relatively low crystal density, which is closely related to the energetic performances. This structural feature makes the preparation of 3D EMOFs with high density important and challenging. Herein, we present an efficient approach to construct 3D-layered EMOFs with strong stacking interactions, particularly the stacking of hydrogen-bridged rings, to solve the aforementioned contradiction. In this strategy, two EMOFs possessing layered structures with the same ligand and the metal center, named 1 and 2, were rationally designed and synthesized. EMOF 1 exhibits a 1D chain structure with a "head-to-tail"stacking mode, while EMOF 2 has a 3D architecture with a "head-to-head"stacking mode. The crystal structure and the molecular interaction analyses disclosed that the stacking of hydrogen-bridged rings in 2 are stronger than that in 1 and they play a more important role than π-stacking in the higher packing efficiency of 2. TG-DSC-MS-FTIR simultaneous tests showed that 2 has better thermal stability due to the improved structural reinforcement. As expected, 2 exhibits higher density, better energetic performance, and safety than 1 and possesses detonation velocity comparable to that of cyclo-1,3,5-trimethylene-2,4,6-trinitramine (RDX). Our approach highlights the importance of the crystal packing architecture and the stacking interactions on the energetic properties of EMOFs and offers a new approach for the design and synthesis of high-performance insensitive energetic complexes.
- Chen, Xiang,Gao, Rong,Guo, Zhaoqi,Ma, Haixia,Zhang, Cong,Zhang, Jianguo
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p. 5436 - 5446
(2020/09/03)
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- Green Energetic Nitrogen-Rich Salts of 1,1′-Dinitramino-5,5′-bistetrazolate
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A series of nitrogen-rich energetic salts of 1,1′-dinitramino-5,5′-bistetrazolate (DNABT) guanidinium (1), aminoguanidinium (2), diaminoguanidinium (3), triaminoguanidinium (4), diaminouronium (5), 3,4-diamino-1,2,4-triazolium (6), and ethylenediammonium (7) was synthesized by a metathesis strategy and characterized by elemental analysis, mass spectrometry, and IR spectroscopy as well as single-crystal X-ray diffraction and differential scanning calorimetry (DSC). The natural bond orbitals (NBOs) and electrostatic potentials (ESPs) were further computed for a better understanding of the structures of the DNABT molecule. The heats of formation were calculated based on the Born–Haber energy cycle. The detonation parameters were evaluated by using the EXPLO5 program, and the sensitivities were measured according to BAM standers. These new salts exhibit highly positive heats of formation (407.0–1377.9 kJ mol?1) and good thermal stabilities (180–211 °C). Most of these compounds possess detonation velocities comparable to RDX and acceptable detonation pressures. The high volumes of explosion gases of the salts 3 and 4 (921 and 933 L kg?1, respectively) further support their power as explosives. The enhancing performances, the fact of being free of metals, and the more moderate sensitivities than K2DNABT, suggest that the salts 4 (D=8851 m s?1, P=29.0 GPa), 5 (D=9053 m s?1, P=32.3 GPa), and 6 (D=8835 m s?1, P=30.2 GPa) might be potential environmentally friendly energetic materials.
- He, Piao,Wu, Le,Wu, Jinting,Wang, Qianyou,Li, Zhimin,Gozin, Michael,Zhang, Jianguo
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supporting information
p. 11159 - 11168
(2017/08/22)
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- Single-molecule magnet behaviour in a tetranuclear DyIII complex formed from a novel tetrazine-centered hydrazone Schiff base ligand
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Two analogous tetranuclear lanthanide complexes have been synthesized with the general formula [Ln4(vht)4(MeOH)8](NO3)4·aMeOH·bH2O, where H2vht = (3,6-bis(vanillidenehydrazinyl)-1,2,4,5-tetrazine) and Ln = DyIII (1), GdIII (2). These complexes are characterized by several techniques; including single-crystal X-ray diffraction, SQUID magnetometry and single-crystal micro-SQUID hysteresis loop measurements. Elucidation of the crystal structure of the complexes shows that the lanthanide ions are bridged by a tetrazine ring, a rare bridging moiety for lanthanide ions. Magnetic studies reveal that both 1 and 2 exhibit weak ferromagnetic exchange interactions between Ln ions, and 1 displaying Single-Molecule Magnet (SMM) behaviour with a magnetisation reversal barrier of Ueff = 158 K (τ0 = 1.06 × 10?7 s).
- Lacelle,Brunet,Pialat,Holmberg,Lan,Gabidullin,Korobkov,Wernsdorfer,Murugesu
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supporting information
p. 2471 - 2478
(2017/03/08)
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- Proposed Proton-Transfer Mechanism for the Initial Decomposition Steps of BTATz
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The first steps in the gas-phase decomposition mechanism of N3,N6-bis (1H-tetrazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine, BTATz, anions and the kinetic isotope effects in these processes were studied using combined multi-stage mass spectrometry (MS/MS) and computational techniques. Two major fragmenta-tion processes, the exergonic loss of nitrogen molecules and the endergonic loss of hydrazoic acid, were identified. The observation of a primary isotope effect supported by calculations, suggests that the loss of a nitrogen molecule from the tetrazole ring involves proton migration, either to, or within the terazole ring, as a rate-determining step. The fragmentation of a hydrazoic acid occurs through an asymmetrical retro pericyclic reaction. Calculations show the relevance of these mechanisms to neutral BTATz. Our findings may contribute to the understanding of decomposition routes in these nitrogen-rich energetic materials and allow tailoring their reactivity and decomposition pathways for better control of performance.
- Parvari, Galit,Levi, Moran,Preshel Zlatsin, Maya,Panz, Larisa,Grinstein, Dan,Gottlieb, Levi,Denekamp, Chagit,Eichen, Yoav
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- High-performing and thermally stable energetic 3,7-diamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole derivatives
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A family of energetic salts based on 3,7-diamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-2-ium were prepared by reaction of 3,7-diamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole (3) with corresponding energetic acids. The nitration product, 7-nitroimino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole (4), was synthesized by using 100% nitric acid. The calculated detonation performance shows that compound 10, composed of 3,7-diamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-2-ium and 3,3′-dinitramino-4,4′-azoxyfurazanate, has good density (1.830 g cm?3), high decomposition temperature (201 °C) and detonation performance (9077 m s?1, 34.4 GPa) as well as acceptable sensitivities (10 J, 240 N), which is superior to those of 1,3,5-trinitroperhydro-1,3,5-triazine (RDX).
- Tang, Yongxing,He, Chunlin,Imler, Gregory H.,Parrish, Damon A.,Shreeve, Jean'ne M.
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p. 6100 - 6105
(2017/04/03)
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- Synthesis of a tetrazine-based catecholamide derivative and its evaluation as a chelating agent for removal of Cd(II), Co(II), and Cu(II)
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The synthesis and structural characterization of a tetrazine-based catecholamide (CAM) ligand, N,N′-bis(N″-(aminoethyl)-2,3-bis(hydroxy)benzamide)-1,2,4,5-tetrazine-3,6-diamine (5), were investigated. All compounds were characterized by 1H NMR spectroscopy, 13C NMR spectroscopy, and FTIR spectroscopy. The protonation equilibria of 5 and complexation capacities (log βpqr) of Cd2+, Co2 +, and Cu2+ complexes of 5 were evaluated through potentiometric titration and spectrophotometric titration, respectively. Species independent pM value (=?log [M]free) was used to compare metal affinities with the final sequence Cu2+?>?Cd2+?>?Co2+. Results show that 5 has potential for heavy metal removal.
- Lei, Shan,Jin, Bo,Peng, Rufang,Zhang, Qingchun,Chu, Shijin
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p. 2384 - 2392
(2017/08/02)
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- Self-Exfoliated Guanidinium-Based Ionic Covalent Organic Nanosheets (iCONs)
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Covalent organic nanosheets (CONs) have emerged as functional two-dimensional materials for versatile applications. Although π-π stacking between layers, hydrolytic instability, possible restacking prevents their exfoliation on to few thin layered CONs from crystalline porous polymers. We anticipated rational designing of a structure by intrinsic ionic linker could be the solution to produce self-exfoliated CONs without external stimuli. In an attempt to address this issue, we have synthesized three self-exfoliated guanidinium halide based ionic covalent organic nanosheets (iCONs) with antimicrobial property. Self-exfoliation phenomenon has been supported by molecular dynamics (MD) simulation as well. Intrinsic ionic guanidinium unit plays the pivotal role for both self-exfoliation and antibacterial property against both Gram-positive and Gram-negative bacteria. Using such iCONs, we have devised a mixed matrix membrane which could be useful for antimicrobial coatings with plausible medical benefits.
- Mitra, Shouvik,Kandambeth, Sharath,Biswal, Bishnu P.,Abdul Khayum,Choudhury, Chandan K.,Mehta, Mihir,Kaur, Gagandeep,Banerjee, Subhrashis,Prabhune, Asmita,Verma, Sandeep,Roy, Sudip,Kharul, Ulhas K.,Banerjee, Rahul
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supporting information
p. 2823 - 2828
(2016/03/12)
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- 3,6,7-Triamino-[1,2,4]triazolo[4,3-b][1,2,4]triazole: A non-toxic, high-performance energetic building block with excellent stability
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A novel strategy for the design of energetic materials that uses fused amino-substituted triazoles as energetic building blocks is presented. The 3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazolium (TATOT) motif can be incorporated into many ionic, nitrogen-rich materials to form salts with advantages such as remarkably high stability towards physical or mechanical stimuli, excellent calculated detonation velocity, and toxicity low enough to qualify them as "green explosives". Neutral TATOT can be synthesized in a convenient and inexpensive two-step protocol in high yield. To demonstrate the superior properties of TATOT, 13 ionic derivatives were synthesized and their chemical- and physicochemical properties (e.g., sensitivities towards impact, friction and electrostatic discharge) were investigated extensively. Low toxicity was demonstrated for neutral TATOT and its nitrate salt. Both are insensitive towards impact and friction and the nitrate salt combines outstanding thermal stability (decomposition temperature=280°C) with promising calculated energetic values. Triaminotriazolotriazolium (TATOT) nitrate (see figure) can be synthesized safely by a two-step protocol. TATOT shows no aquatic toxicity, excellent stability towards thermal and physical stimuli, as well as good energetic performance. The TATOT cation is a "green", inexpensive energetic building block and a promising alternative to currently used nitrogen-rich cations, such as hydrazinium, hydroxylammonium, or guanidinium cations.
- Klap?tke, Thomas M.,Schmid, Philipp C.,Schnell, Simon,Stierstorfer, J?rg
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p. 9219 - 9228
(2015/06/16)
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- Kinetic study on the aromatic nucleophilic substitution reaction of 3,6-dichloro-1,2,4,5-tetrazine by biothiols
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The aromatic nucleophilic substitution reaction of 3,6-dichloro-1,2,4,5- tetrazine (DCT) with a series of biothiols RSH: (cysteine, homocysteine, cysteinyl-glycine, N-acetylcysteine, and glutathione) is subjected to a kinetic investigation. The reactions are studied by following spectrophotometrically the disappearance of DCT at 370nm. In the case of an excess of N-acetylcysteine and glutathione, clean pseudo first-order rate constants (kobs1) are found. However, for cysteine, homocysteine and cysteinyl-glycine, two consecutive reactions are observed. The first one is the nucleophilic aromatic substitution of the chlorine by the sulfhydryl group of these biothiols (RSH) and the second one is the intramolecular and intermolecular nucleophilic aromatic substitutions of their alkylthio with the amine group of RSH to give the di-substituted compound. Therefore, in these cases, two pseudo first-order rate constants (kobs1 and kobs2, respectively) are found under biothiol excess. Plots of kobs1 versus free thiol concentration at constant pH are linear, with the slope (kN) independent of pH (from 6.8 to 7.4). The kinetic data analysis (Bronsted-type plot and activation parameters) is consistent with an addition-elimination mechanism with the nucleophilic attack as the rate-determining step. Copyright
- Andrade-Acuna, Daniela,Santos, Jose G.,Tiznado, William,Canete, Alvaro,Aliaga, Margarita E.
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p. 670 - 675
(2014/08/18)
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- A tetrazine templated method for the synthesis of ternary conjugates
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Conjugation is an important reaction that enables coupling of molecules. Many protocols exist for the synthesis of binary conjugates from two different molecules or for the polyvalent display of a single molecule. There aren't many methods for the synthesis of ternary conjugates. However, methods for ternary conjugation are important for understanding the interplay of interactions between three biomolecules (or any three molecules per se). A strategy for ternary bioconjugation using inverse electron demand Diels-Alder reaction with tetrazine is studied. Ternary conjugation was demonstrated by the reaction of a model glyco-peptide binary conjugate with a fluorescent tagged olefin. The Royal Society of Chemistry 2013.
- Venkateswara Rao, Boddu,Dhokale, Snehal,Rajamohanan, Pattuparambil R.,Hotha, Srinivas
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supporting information
p. 10808 - 10810
(2013/11/06)
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- Synthesis, spectroscopic and thermal characterization of azido-1,2,4-triazoles: A class of heteroarenes with a high nitrogen content
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The syntheses of azido-1,2,4-triazoles 1-5 were carried out from triaminoguanidine hydrochloride and a carboxylic acid (formic, acetic, 2,2,2-trifluoroacetic, 2-benzylacetic, monochloroacetic acid) by a three-step synthetic route and were analyzed by accelerating rate calorimetry (ARC). The thermal decomposition of 1-5 was studied theoretically by using CHETAH and T1 software, and experimentally by using DSC to obtain kinetic data. Numerical modelling and mass spectrometry were also performed to estimate the nature of the intrinsic molecular reactivity of 1-5 and the possible early stages of a self-heating process. Complete optimization by using HF, B3LYP and MP2(full) methods at the 6-31G* level were performed on significant tautomeric forms of the azido-triazoles to confirm the electronic structures that were obtained by EI-MS. We have synthesized azido-1,2,4-triazoles 1-5 from triaminoguanidine hydrochloride and a carboxylic acid by a three-step route. The procedure has been optimized from a "green agreeability" point of view. The thermal decomposition of 1-5 has been investigated theoretically by using predictive software, and experimentally by using differential scanning calorimetry. Copyright
- Cardillo, Paolo,Dellavedova, Marco,Gigante, Lucia,Lunghi, Angelo,Pasturenzi, Christian,Salatelli, Elisabetta,Zanirato, Paolo
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supporting information; experimental part
p. 1195 - 1201
(2012/04/10)
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- The reactivity of 5-cyanotetrazole towards water and hydroxylamine
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Sodium 5-cyanotetrazolate sesquihydrate (1) was prepared from sodium azide and two equivalents of sodium cyanide under acidic conditions. Its hydrolysis, when treated with an excess of 6m nitric acid yields tetrazole-5-carboxamide (4), whereas stoichiomet
- Fischer, Niko,Klapoetke, Thomas M.,Rappenglueck, Sebastian,Stierstorfer, Joerg
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p. 877 - 888
(2014/01/17)
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- Antimalarial 3-arylamino-6-benzylamino-1,2,4,5-tetrazines
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We report on novel 3-arylamino-6-benzylamino-1,2,4,5-tetrazines with potent activity against Plasmodium falciparum.
- Nhu, Duong,Duffy, Sandra,Avery, Vicky M.,Hughes, Andrew,Baell, Jonathan B.
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supporting information; experimental part
p. 4496 - 4498
(2010/10/02)
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- Synthesis and physical chemistry of s-tetrazines: Which ones are fluorescent and why?
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New fluorescent tetrazines have been prepared and their electrochemistry and fluorescence efficiency evaluated. The occurrence of fluorescence as well as the wavelength were found to be strongly dependent on the substituents, which have to be electronegative heteroatoms. This has been rationalized through a computational study that showed that the crucial factor is the nature of the HOMO, which determines the existence or not: of fluorescence. Wiley-VCH Verlag GmbH & Co. KGaA.
- Gong, Yong-Hua,Miomandre, Fabien,Meallet-Renault, Rachel,Badre, Sophie,Galmiche, Laurent,Tang, Jie,Audebert, Pierre,Clavier, Gilles
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supporting information; experimental part
p. 6121 - 6128
(2010/03/24)
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- An Improved Synthesis of 3,6-Diamino-1,2,4,5-tetrazine. II. From Triaminoquanidine and 2,4-Pentanedione
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A new synthesis for the title compound that gives an 80percent overall yield was developed.Treatment of triaminoguanidine monohydrochloride (1) with 2,4-pentanedione (2) gave 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2-dihydro-1,2,4,5-tetrazine (3) in 80-85percent yield.Oxidation of 3 with nitric oxide or nitrogen dioxide to 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine (4) followed by ammonolysis of 4 gave 3,6-diamino-1,2,4,5-tetrazine (5) in quantitatively yields
- Coburn, M.D.,Buntain, G.A.,Harris, B.W.,Hiskey, M.A.,Lee, K.-Y.,Ott, D.G.
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p. 2049 - 2050
(2007/10/02)
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