2510-22-7Relevant academic research and scientific papers
Synthesis and characterization of two different azarubrenes
Xie, Gaozhan,Hahn, Sebastian,Rominger, Frank,Freudenberg, Jan,Bunz, Uwe H. F.
, p. 7593 - 7596 (2018)
The synthesis, properties and solid state X-ray single crystal structures of two new rubrene-derivatives, viz diazarubrene (4,4′-(6,12-diphenyltetracene-5,11-diyl)dipyridine) and tetraazarubrene (5,6,11,12-tetra(pyridin-4-yl)tetracene), are reported. Both the azarubrenes are more oxidatively stable than rubrene itself and show very similar optical properties but differ in their crystal packing from that of rubrene.
Synergetic effect of host-guest chemistry and spin crossover in 3D hofmann-like metal-organic frameworks [Fe(bpac)M(CN)4] (M=Pt, Pd, Ni)
Bartual-Murgui, Carlos,Salmon, Lionel,Akou, Amal,Ortega-Villar, Norma A.,Shepherd, Helena J.,Munoz, M. Carmen,Molnar, Gabor,Real, Jose Antonio,Bousseksou, Azzedine
, p. 507 - 516 (2012)
The synthesis and characterization of a series of three-dimensional (3D) Hofmann-like clathrate porous metal-organic framework (MOF) materials [Fe(bpac)M(CN)4] (M=Pt, Pd, and Ni; bpac=bis(4-pyridyl)acetylene) that exhibit spin-crossover behavior is reported. The rigid bpac ligand is longer than the previously used azopyridine and pyrazine and has been selected with the aim to improve both the spin-crossover properties and the porosity of the corresponding porous coordination polymers (PCPs). The 3D network is composed of successive {Fe[M(CN)4]}n planar layers bridged by the bis-monodentate bpac ligand linked in the apical positions of the iron center. The large void between the layers, which represents 41.7% of the unit cell, can accommodate solvent molecules or free bpac ligand. Different synthetic strategies were used to obtain a range of spin-crossover behaviors with hysteresis loops around room temperature; the samples were characterized by magnetic susceptibility, calorimetric, Moessbauer, and Raman measurements. The complete physical study reveals a clear relationship between the quantity of included bpac molecules and the completeness of the spin transition, thereby underlining the key role of the π-π stacking interactions operating between the host and guest bpac molecules within the network. Although the inclusion of the bpac molecules tends to increase the amount of active iron centers, no variation of the transition temperature was measured. We have also investigated the ability of the network to accommodate the inclusion of molecules other than water and bpac and studied the synergy between the host-guest interaction and the spin-crossover behavior. In fact, the clathration of various aromatic molecules revealed specific modifications of the transition temperature. Finally, the transition temperature and the completeness of the transition are related to the nature of the metal associated with the iron center (Ni, Pt, or Pd) and also to the nature and the amount of guest molecules in the lattice. Copyright
Tuning supramolecular aurophilic structures: The effect of counterion, positive charge and solvent
Aguiló, Elisabet,Gavara, Raquel,Baucells, Clara,Guitart, Marta,Lima, Jo?o Carlos,Llorca, Jordi,Rodríguez, Laura
, p. 7328 - 7339 (2016)
The synthesis of the cationic gold(i) complexes [Au(C≡CC5H4N)(CH3-PTA)]X (X = I, 1; X = OTf, 4), [Au(C≡CC5H4N-CH3)(PTA)]X (X = I, 2; X = OTf = 5; PTA = 1,3,5-triaza-7-phosphatricyclo[3.3.1.13.7]decane) and [Au(C≡CC5H4N-CH3)(DAPTA)]X (X = I, 3; X = OTf = 6, DAPTA = 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane) results in cationic complexes with unexpected supramolecular assemblies in water ranging from rod-like structures (1) to vesicles (2 and 3) and square-like structures (5 and 6). These morphologies are completely different from the fibers previously obtained with their parent neutral complexes [Au(C≡C5H4N)(PTA)] and [Au(C≡C5H4N)(DAPTA)]. Nevertheless, the introduction of triflate as a counterion in 1 (complex 4) gives rise to the formation of a highly soluble complex in water which does not display any significant aggregation in solution. These results reveal the importance of the introduction of a positive charge on global supramolecular assemblies and how the counterion can also modify the resulting package. Interestingly, we have also proved that the aggregation of complexes 2, 3, 5 and 6 is also affected by the solvent with direct influence on their absorption and emission properties and the global morphology of the aggregates.
Synthesis, Electrochemistry, and Optical Properties of Highly Conjugated Alkynyl-Ferrocenes and -Biferrocenes
Bennett, Troy L. R.,Wilkinson, Luke A.,Lok, Jasmine M. A.,O'Toole, Robert C. P.,Long, Nicholas J.
, p. 1156 - 1162 (2021/05/06)
Sonogashira reactions are utilized herein to react iodo-ferrocenes and -biferrocenes with terminal alkyne ligands, functionalized with both pyridine and thioanisole groups. High-yielding reactions generate both monoalkynyl and dialkynyl derivatives, the r
Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors
Keeley,ábrányi-Balogh,Keseru
supporting information, p. 263 - 267 (2019/03/05)
A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads. The analysis of theoretical and experimental descriptors revealed correlations between the electronic properties of the heterocyclic cores and their reactivity against GSH that are helpful in identifying suitable fragments for cysteines with specific nucleophilicity. The most important advantage of these fragments is that they show only minimal structural differences from non-electrophilic counterparts. Therefore, they could be used effectively in the design of targeted covalent inhibitors with minimal influence on key non-covalent interactions.
Synthesis, optical spectroscopy, structural, and DFT studies on dimeric iodo-bridged Copper(I)complexes
Haque, Ashanul,Al Balushi, Rayya A.,Al-Busaidi, Idris Juma,Ilmi, Rashid,Al Rasbi, Nawal,Jayapal, Maharaja,Khan, Muhammad S.,Raithby, Paul R.
, p. 75 - 82 (2019/05/10)
Three new iodo-bridged copper(I)complexes of the type [CuI(PPh3)L]2, where L = Ar–≡–C5H4N, Ar = phenyl (C1), biphenyl (C2)and flourenyl (C3)have been synthesized via coordination-driven self-assembly processes. Two of Cu(I)complexes, C2 and C3, have been characterized by single-crystal X-ray diffraction studies. The complexes have two molecules of the P-donor ligand and two molecules of the N-donor ligand in trans configurations, supporting the central Cu2I2 unit. Absorption properties of the complexes have been investigated. Extensive DFT calculation has been carried out to delineate the influence of aromatic spacers on the optical properties and the nature of excited states. The ease of synthesis of these Cu(I)dimers and the wide range of ethynylpyridine supporting ligands that can be incorporated highlights the potential for these materials to form polymers by linking through the ethylylpyridine ligands.
INHIBITORS FOR THE Β-CATENIN / T-CELL FACTOR PROTEIN–PROTEIN INTERACTION
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Page/Page column 37; 38, (2019/10/23)
Disclosed are inhibitors for the β-catenin/T-cell factor interaction. The inhibitors are selective for β-catenin/T-cell factor over β-catenin/cadherin and β-catenin/APC interactions. Methods of using the disclosed compounds to treat cancer are also disclosed.
Supramolecular Chemistry of Some Metal Acetylacetonates with Auxiliary Pyridyl Sites
Gunawardana, Chamara A.,Sinha, Abhijeet S.,Desper, John,Lakovi?, Marijana,Aaker?y, Christer B.
, p. 6936 - 6945 (2018/10/20)
Hetero-bifunctional ligands can pave the way for elaborate metallo-supramolecular systems and are also useful for combining metal-ligand bonding with other types of noncovalent interactions. We synthesized two new pyridyl-acetylacetonate ligands, 3-(4-(pyridin-4-yl)phenyl)pentane-2,4-dione (L1) and 3-(4-(pyridin-4-ylethynyl)phenyl)pentane-2,4-dione (L2), and explored their metal binding ability with selected di- and trivalent transition metal ions. As expected, the acetylacetonate ligation with metal dications remains consistent among four structures, [Cu(L1)2(MeOH)2]n, [Co(L2)2]n, [Cu(L2)2(MeOH)2], and [Zn(L2)2(MeOH)2]; the metal is four-coordinate and resides in a square planar environment. Differences in the overall architectures arise basically from the role played by the terminal heterocycle (i.e., the pyridyl group). In [Cu(L1)2(MeOH)2]n and [Co(L2)2]n, the heterocyclic end directly binds to the metal (through vacant axial positions), thereby producing coordination networks. In [Cu(L2)2(MeOH)2] and [Zn(L2)2(MeOH)2], metal-methanol coordination and intermolecular O-H(methanol)···N(pyridine) hydrogen-bond interactions work in concert to weave those bis-acetylacetonate complexes into ribbon-like supramolecular polymeric arrays. Somewhat surprisingly, the only tris-chelated acetylacetonate complex characterized in this study, [Fe(L2)3], essentially exists as discrete dimeric aggregates.
Dicopper(I) Complexes Incorporating Acetylide-Functionalized Pyridinyl-Based Ligands: Synthesis, Structural, and Photovoltaic Studies
Jayapal, Maharaja,Haque, Ashanul,Al-Busaidi, Idris J.,Al-Rasbi, Nawal,Al-Suti, Mohammed K.,Khan, Muhammad S.,Al-Balushi, Rayya,Islam, Shahidul M.,Xin, Chenghao,Wu, Wenjun,Wong, Wai-Yeung,Marken, Frank,Raithby, Paul R.
, p. 12113 - 12124 (2018/09/27)
Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1-L6) with the general formula Py-C≡C-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2′-bithiophene]-5-yl, 2,2′:5′,2″-terthiophene]-5-yl, thieno[2,3-b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been synthesized by Pd(0)/Cu(I)-catalyzed cross-coupling reaction of 4-ethynylpyridine and the respective heteroaryl halide. Ligands L1-L6 were isolated in respectable yields and characterized by microanalysis, IR spectroscopy, 1H NMR spectroscopy, and ESI-MS mass spectrometry. A series of dinuclear Cu(I) complexes 1-10 have been synthesized by reacting L1-L6 with CuI and triphenylphosphine (PPh3) (R1) or with an anchored phosphine derivative, 4-(diphenylphosphino) benzoic acid (R2)/2-(diphenylphosphino)benzenesulfonic acid (R3), in a stoichiometric ratio. The complexes are soluble in common organic solvents and have been characterized by analytical, spectroscopic, and computational methods. Single-crystal X-ray structure analysis confirmed rhomboid dimeric structures for complexes 1, 2, 4, and 5, and a polymeric structure for 6. Complexes 1-6 showed oxidation potential responses close to 0.9 V vs Fc0/+, which were chemically irreversible and are likely to be associated with multiple steps and core oxidation. Preliminary photovoltaic (PV) results of these new materials indicated moderate power conversion efficiency (PCE) in the range of 0.15-1.56% in dye-sensitized solar cells (DSSCs). The highest PCE was achieved with complex 10 bearing the sulfonic acid anchoring functionality.
Chemistry of 4-[(4-bromophenyl)ethynyl]pyridine at metal surfaces studied by STM
Ren, Jindong,Larkin, Eugene,Delaney, Colm,Song, Yang,Jin, Xin,Amirjalayer, Saeed,Bakker, Anne,Du, Shixuan,Gao, Hongying,Zhang, Yu-Yang,Draper, Sylvia M.,Fuchs, Harald
supporting information, p. 9305 - 9308 (2018/08/29)
Molecular architectures (Kagome networks, coordinated/covalent dimers and branched coordination chains) via self-assembly, Ullmann reaction and pyridine coordination of 4-[(4-bromophenyl)ethynyl]pyridine are found to be sensitive to the underlying metallic surfaces. The molecular species were characterised on the surface by low-temperature scanning tunnelling microscopy (LT-STM) at sub-molecular level.
