Synthesis and properties of benzocyclobutene-terminated imide-containing cyano group

Benzocyclobutene (BCB) resins have aroused much interest because of their excellent physical and chemical properties. Unfortunately the temperature required to induce cross-linking in typical BCBs is higher than 250°C, which restricts their applications. In this study, a novel cyano-containing BCB-terminated imide monomer was synthesized through the reaction of 1-cyano-5-amino-benzocyclobutene with 4,4′-oxydiphthalic anhydride. This monomer allows a 50–100°C lower curing temperature in comparison with typical BCBs, and it is highly soluble in various solvents and can easily convert to cured film at 150–200°C. Because of the presence of rigid imide group and strong polar cyano group, the cured film exhibits excellent mechanical strength with tensile strength up to 87.8 MPa, high glass transition temperature up to 350°C, low coefficient of thermal expansion (36.9 ppm K−1), and outstanding planarity with the average surface roughness as low as 0.26 nm.

Synthesis, properties and gas separation performance of poly(arylene ether sulfone) containing imide pendant groups

Three kinds of pendant imide group were introduced into poly(arylene ether sulfone) via an imidization approach.

Vinyl monomers bearing a sulfonyl(trifluoromethane sulfonyl) imide group: synthesis and polymerization using nitroxide-mediated polymerization

A series of water-soluble styrene and propyl (meth)acrylate based monomers bearing a sulfonyl(trifluoromethane sulfonyl) imide (STFSI) group was prepared.

Cocrystals of the antibiotic trimethoprim with glutarimide and 3,3-dimethylglutarimide held together by three hydrogen bonds

The antibiotic trimethoprim [5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine] was cocrystallized with glutarimide (piperidine-2,6-dione) and its 3,3-dimethyl derivative (4,4-dimethylpiperidine-2,6-dione). The cocrystals,viz.trimethoprim–glutarimide (1/1), C14H18N4O3·C5H7NO2, (I), and trimethoprim–3,3-dimethylglutarimide (1/1), C14H18N4O3·C7H11NO2, (II), are held together by three neighbouring hydrogen bonds (one central N—H...N and two N—H...O) between the pyrimidine ring of trimethoprim and the imide group of glutarimide, with anADA/DADpattern (A= acceptor andD= donor). These heterodimers resemble two known cocrystals of trimethoprim with barbituric acid and its 5,5-diethyl derivative. Trimethoprim shows a conformation in which the planes of the pyrimidine and benzene rings are approximately perpendicular to one another. In its glutarimide coformer, five of the six ring atoms lie in a common plane; the C atom opposite the N atom deviates by about 0.6 Å. The crystal packing of each of the two cocrystals is characterized by an extended network of hydrogen bonds and contains centrosymmetrically related trimethoprim homodimers formed by a pair of N—H...N hydrogen bonds. This structural motif occurs in five of the nine published crystal structures in which neutral trimethoprim is present.

N-(3-Chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-propionylpropionamide

In the title molecule, C16H14ClNO4, the four essentially planar atoms of the imide group [r.m.s. deviation = 0.0286 (11) Å] form a dihedral angle of 77.36 (13)° with the naphthoquinone group [maximun deviation = 0.111 (2) Å for the carbonyl O atom in the naphthalene 1-position] and the two imide carbonyl groups are orientedantiwith respect to each other. In the crystal, molecules are connected by weak C—H...O hydrogen bonds, as well as π–π stacking interactions [centroid–centroid distance = 3.888 (3) Å], forming a three-dimensional network.

A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides

A regioselective synthesis has been developed for the preparation of a series ofN,N′-disubstituted 4,4′-carbonylbis(carbamoylbenzoic) acids andN,N′-disubstituted bis(carbamoyl) terephthalic acids by treatment of 3,3′,4,4′-benzophenonetetracarboxylic dianhydride (1) and 1,2,4,5-benzenetetracarboxylic dianhydride (2) with arylalkyl primary amines (A-N). The carbamoylcarboxylic acid derivatives were synthesized with good yield and high purity. The specific reaction conditions were established to obtain carbamoyl and carboxylic acid functionalities over the thermodynamically most favored imide group. Products derived from both anhydrides1and2were isolated as pure regioisomeric compounds under innovative experimental conditions. The chemo- and regioselectivity of products derived from dianhydrides were determined by NMR spectroscopy and confirmed by density functional theory (DFT). All products were characterized by NMR, FTIR, and MS.

Supramolecular Assembly of Functional Cholesteryl Substituted Luminol Derivative in Organized Molecular Films

Functional luminol derivative with cholesteryl substituted group has been designed and synthesized from the reaction of the corresponding precursor cholesteryl chloroformate with luminol. This compound can be spread on water surface to form stable monolayer. It has been found that UV and IR spectra confirmed the characteristic aromatic segment, imide group and cholesteryl substituted group. In addition, the CD spectra also showed positive CD signals, which may be attributed to the chiral cholesteryl substituted groups. AFM investigation indicated some aggregated domains with the averaged height about 3.6  0.2 nm appeared. This suggested an organized structure of double molecules may be fabricated in the transferred LB films. The present results have demonstrated that the interfacial properties of luminol derivative can be modified by changing proper substituted groups of luminol, which show potential application in functional material fields such as ECL sensor.

Synthesis and Characterization of Functional Cholesteryl Substituted Luminol Derivative

Functional luminol derivative with cholesteryl substituted group has been designed and synthesized from the reaction of the corresponding precursor cholesteryl chloroformate with luminol. It has been found that depending on cholesteryl substituted group, the formed luminol derivative showed different properties, indicating distinct regulation of molecular skeleton. UV and IR data confirmed commonly the formation of imide group as well as cholesteryl segment in molecular structure. Thermal analysis showed that the thermal stability of luminol derivative with cholesteryl segment was different from luminol. The difference of thermal stability is mainly attributed to the formation of imide group and cholesteryl substituent group in molecular structure. The present results have demonstrated that the special properties of luminol derivative can be turned by modifying molecular structure of objective compound with proper substituted groups, which show potential application in functional material fields such as liquid crystal and ECL sensor.