7710-20-5Relevant academic research and scientific papers
Highly sheared anti-parallel dipolar carbonylcarbonyl interaction in the crystal packing of strapped crown-3-pyromellitimide
Howe, Ethan Nam Wei,Bhadbhade, Mohan,Thordarson, Pall
, p. 1384 - 1389 (2012)
Non-covalent dipolar interactions between pairs of carbonyls have been demonstrated to play a significant role in the crystal packing and formation of supramolecular structural architecture of small organic molecules. Under high dilution, the strapped crown-3-pyromellitimide 4 and macrocyclic crown-6-bispyromellitimide 5 were synthesised in concert and demonstrated selective molecular recognition towards Na+ and K+, respectively. The molecular structure of strapped crown-3-pyromellitimide 4 was solved using X-ray crystallography and an unusual highly sheared anti-parallel dipolar carbonylcarbonyl interaction was observed in the crystal packing. The intermolecular interaction has a torsion angle of 44.1, and deviates from the three idealised motifs reported in literature. This finding further highlights the importance and versatility of dipolar carbonylcarbonyl interaction in the crystal packing of organic molecules.
Axial Ligation Constants of Iron(II) and Cobalt(II) "Capped" Porphyrins
Ellis, Paul E.,Linard, Jack E.,Szymanski, Thomas,Jones, Robert D.,Budge, John R.,et al.
, p. 1889 - 1896 (1980)
Equilibrium constants for addition of ligands to cobalt(II) and iron(II) complexes of the "capped" and "homologous capped" porphyrins are reported.For the equilibrium FeII(cap) + B FeII(Cap)(B) (KB), a plot of log KB vs. the pKa of the conjugate acid of the ligand shows a linear relationship among structurally similar base ligands. ?-Bonding ligands form more stable complexes than predicted by their pKa values.Sulfur base binding to CoII(Cap) shows a relative binding order for S-donor ligands of thiolates >> thioethers > mercaptans.Unlike the Fe(Cap), which can bind only one axial base ligand, Fe(HmCap) can bind two small ligands axially in the usual manner.Intermediate-size ligands, such as 1-methylimidazole, however, weakly coordinate a second base leading to an unusual six-coordinate complex with an intermediate electronic spin of S = 1.
Study of the thermal degradation of benzene-containing glycerol carbonate derivatives by a combined TG–FTIR and theoretical calculation
Liu, Jing,Li, Rujuan,Guo, Mengya,Tao, Hairong,Sun, Donglan,Zong, Chengxing,Liu, Chunjing,Fu, Fengzhi
, p. 179 - 185 (2017)
We recently found that the introduction of benzene ring as connection block improved the thermal stability of glycerol carbonate derivatives. To further explore how polysubstitution on benzene influences their thermal stability, another two derivatives, benzene-1,3,5-tricarboxylic acid tris-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (BATE1) and benzene-1,2,4,5-tetracarboxylic acid tetrakis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (BATE2), were synthesized and characterized by a combined TG–FTIR and theoretical calculation. TG results showed that both BATE1 and BATE2 had three weight loss stages. FTIR spectra of evolved gases and the bond dissociation energy for the two compounds indicated that during the pyrolysis process, the C[sbnd]C, C[sbnd]O bonds of five-membered cyclic carbonate fractured preferentially to produce volatile carbonates and CO2, and then the nearby C[sbnd]O bond of esters continued to crack to produce more fragments. Finally, benzene ring still remains in the solid pyrolysis products. Therefore, improving the thermal stability of compound cannot be achieved simply by increasing the number of substituents on the benzene ring.
Aromatic Esters, Carbinols, and Derivatives Thereof with Perfluorohexyl Residues as Alternatives to Perfluoroalkanecarboxylic and -sulfonic Acids
Alpers, Torben,Muesmann, Thomas W. T.,Temme, Oliver,Christoffers, Jens
, p. 609 - 617 (2017/02/05)
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.
2,6-diphospha-s-indacene-1,3,5,7(2H,6H)-tetraone: A phosphorus analogue of aromatic diimides with the minimal core exhibiting high electron-accepting ability
Takeda, Youhei,Nishida, Takuya,Minakata, Satoshi
supporting information, p. 10266 - 10270 (2014/08/18)
Phosphorus analogues of pyrromellitic diimides (PyDIs), which represent a family of privileged electron-accepting organic compounds, have been successfully synthesized as novel electron-accepting π-conjugated molecules. Investigation into their physicochemical properties uncovered their prominent electron-accepting abilities over the corresponding PyDI. Furthermore, theoretical studies revealed the significant contribution of σ*-π* hyperconjugation in stabilizing the LUMO+1.
Two-dimensional nanostructures by the assembly of n-type tetraazaanthracene-based conjugated molecules
He, Chunyang,Wu, Dongqing,Zhang, Fan,Xue, Minzhao,Zhuang, Xiaodong,Qiu, Feng,Feng, Xinliang
, p. 2954 - 2960 (2013/10/01)
On the basis of our previous communication concerning a new family of thiophene-armed tetraazaanthracene molecules, we present a further intensive investigation on this class of compounds substituted with different alkyl chains and their self-assembled two-dimensional (2D) nanostructures. These tetraazaanthracene molecules with different alkyl chains were prepared in good yields using the synthetic strategy we developed. In addition to the expected typical n-type character, one compound exhibited aggregation behavior upon electrochemical reduction. Moreover, all molecules in the neutral state showed a strong tendency to aggregate in a binary solvent, as confirmed by optical spectral measurements. To investigate such self-assembly behavior, a phase-transfer method with a dichloromethane/methanol (2:3) binary solvent system was used to prepare the nanostructures. By means of atomic force microscopy, transmission electron microscopy, and X-ray diffraction, we found that the morphology of assembled 2D sheet-like structures could be adjusted by varying the alkyl chain. The weak interactions arising from the heteroatoms (N and S) in the conjugated backbones play a key role in the formation and stabilization of layered structures. Ruling chains: A set of n-type conjugated molecules containing a tetraazaanthracene core and different alkyl-chain arms is presented. In binary solvent mixtures, self-assembly into 2D sheet-like nanostructures takes place (see picture). By using different alkyl chains, morphology can be sensibly modified. The weak interactions arising from the heteroatoms in the conjugated backbones play a key role in the formation and stabilization of the layered structures.
Efficient synthesis and physical properties of novel H-shaped 2,3,7,8-tetraazaanthracene-based conjugated molecules
Liu, Yinque,Zhang, Fan,He, Chunyang,Wu, Dongqing,Zhuang, Xiaodong,Xue, Minzhao,Liu, Yangan,Feng, Xinliang
supporting information; experimental part, p. 4166 - 4168 (2012/05/31)
A series of novel H-shaped molecules consisting of a 2,3,7,8- tetraazaanthracene core and thiophene arms have been developed. The electrochemical study reveals their typical n-type characters. The solid state packing and optoelectronic properties of these molecules can be finely tuned via modification of the substituents.
Triazole- and triazolium-containing porphyrin-cages for optical anion sensing
Gilday, Lydia C.,White, Nicholas G.,Beer, Paul D.
experimental part, p. 7092 - 7097 (2012/07/14)
Triazole and triazolium groups have been integrated into a zinc(ii) metalloporphyrin-based structural framework to produce two porphyrin-cages for anion sensing applications. UV/visible spectroscopic titration investigations reveal both host systems exhibit strong anion binding affinities, with the positively-charged triazolium-porphyrin cage capable of colorimetric sensing halides, fluoride and chloride, and oxoanions in acetone-water solvent mixtures.
A multifunctional porous organic schottky barrier diode
Dalapati, Sasanka,Saha, Rajat,Jana, Sankar,Patra, Astam K.,Bhaumik, Asim,Kumar, Sanjay,Guchhait, Nikhil
supporting information, p. 12534 - 12537 (2013/02/23)
Mesoporous materials: A multifunctional porous organic material (ANPPIT; see picture) has been synthesized and characterized. Multifunctionality of the compound has been determined from nitrogen adsorption, guest-dependent luminescence, and electrical conductivity measurements. Copyright
Excited State Luminescence of Multi-(5-phenyl-1, 3, 4-oxadiazo-2-yl) benzenes in an Electron-Donating Matrix: Exciplex or Electroplex?
Yang, Chih-Chiang,Hsu, Chia-Jung,Chou, Pi-Tai,Cheng, Hsu Chun,Su, Yuhlong Oliver,Leung, Man-Kit
experimental part, p. 756 - 768 (2010/06/21)
Multi-(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzenes show emission in organic solvents from ultraviolet to blue (339-447 nm). The reduction potentials E 1/2red cover a large range of -2.11 V for 2, 5-diphenyl-1, 3, 4-oxadiazole to -0.76 V for 1, 2, 3, 4, 5, 6-hexa(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzene. An unexpectedly wide spectral range of the oxadiazole (OXD) exciplex emissions in PVK is observed, ranging from 406 to 603 nm. The OXDs also exhibit similar electroluminescence (EL) when blended into polyvinylcarbazole (PVK). A linear correlation between the λ max of the electroluminescence and photoluminescence is observed, implying that the emission mechanisms in both processes are similar. In addition, the linear correlation between the E1/2red versus λmax of EL (eV) reflected that the term of the charge-transfer configuration of the contact electron-hole pair plays a major role in the exciplex emission. The exciplex EL of 1, 2, 5-tri(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzene (5) could be as high as 1.0 cd/A. Since the exciplex emission usually has a large Stokes shift, this provides a window for us to generate duo emissions for near white light EL with high efficiency. Among the devices we tried, the device of PVK/2-tert-butylphenyl-5-biphenyl-1, 3, 4-oxadiazole/5/2, 5, 8, 11-tetra-tert-butylperylene (100:40:40:4) gave EL with good current efficiency of 1.63 cd/A.
