5329-29-3Relevant academic research and scientific papers
Supramolecular Metallacycles and Their Binding of Fullerenes
Ehnbom, Andreas,G?b, Christian R.,Oppel, Iris M.,Sturm, Lisa,Tobe, Yoshito
, (2019)
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.
Dynamic and static excimer: A versatile platform for single component white-light emission and chelation-enhanced fluorescence
Kumar, Virendra,Sk, Bahadur,Kundu, Subhankar,Patra, Abhijit
, p. 12086 - 12094 (2018)
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.
A novel sensitive turn-on fluorescent Zn2+ chemosensor based on an easy to prepare C 3-symmetric schiff-base derivative in 100% aqueous solution
Zhou, Ying,Li, Zhan-Xian,Zang, Shuang-Quan,Zhu, Yan-Yan,Zhang, Hong-Yan,Hou, Hong-Wei,Mak, Thomas C. W.
, p. 1214 - 1217 (2012)
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.
Preparation and characterization of bis(guanidinium) and bis(aminotetrazolium)dodecahydroborate salts: Green high energy nitrogen and boron rich compounds
Sharon, Pessia,Afri, Michal,Mitlin, Sergey,Gottlieb, Levi,Schmerling, Bruria,Grinstein, Dan,Welner, Shmuel,Frimer, Aryeh A.
, p. 71 - 89 (2019)
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.
A knot-linker planarity control strategy for constructing highly crystalline cationic covalent organic frameworks: Decoding the effect of crystallinity on adsorption performance
Da, Hong-Ju,Qian, Hai-Long,Yan, Xiu-Ping,Yang, Cheng-Xiong
, p. 12657 - 12664 (2020)
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
Prostate cancer biomarker citrate detection using triaminoguanidinium carbon dots, its applications in live cells and human urine samples
Rajalakshmi, Kanagaraj,Deng, Tongtong,Muthusamy, Selvaraj,Xie, Meng,Xie, Jimin,Lee, Kang-Bong,Xu, Yuanguo
, (2021/12/13)
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.
A: C 3-symmetric twisted organic salt as an efficient mechano-/thermo-responsive molecule: A reusable and sensitive fluorescent thermometer
Prusti, Banchhanidhi,Samanta, Pralok K.,English, Niall J.,Chakravarty, Manab
supporting information, p. 12321 - 12324 (2021/11/30)
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.
Alkaline earth metal salts of 3,6-bis-nitroguanyl-1,2,4,5-tetrazine: Promising perchlorate-free environmentally friendly pyrotechnic components
Chen, Xiang,Chen, Yuankai,Guo, Zhaoqi,Hu, Yongpeng,Ma, Haixia,Wang, Shenghui,Zhang, Cong
, (2021/11/10)
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.
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
Chen, Xiang,Gao, Rong,Guo, Zhaoqi,Ma, Haixia,Zhang, Cong,Zhang, Jianguo
, p. 5436 - 5446 (2020/09/03)
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.
Single-molecule magnet behaviour in a tetranuclear DyIII complex formed from a novel tetrazine-centered hydrazone Schiff base ligand
Lacelle,Brunet,Pialat,Holmberg,Lan,Gabidullin,Korobkov,Wernsdorfer,Murugesu
supporting information, p. 2471 - 2478 (2017/03/08)
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).
