- Synthesis and memory characteristics of novel soluble polyimides based on asymmetrical diamines containing carbazole
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Two novel asymmetrical carbazole-based diamines 9-(2-(1,1′-binaphthyl-4-yl)benzyl)-9H-carbazole-3,6-diamine (BNBCD) and 9-((4′-(9H-carbazol-9-yl)biphenyl-2-yl)methyl-9H-carbazole-3,6-diamine (CBMCD) were synthesized. A series of novel soluble aromatic polyimides were prepared from these diamines by poly-condensation with Pyromelitic dianhydride (PMDA) and 2,2′,3,3′-biphenyl tetracarboxylic dianhydride (BPDA) via a two-step procedure. The resulting polymers were fully characterized, they exhibited excellent organosolubility and high thermal stability with the temperature of 5% weight loss under nitrogen atmosphere over 400°C. Resistive switching devices with the configuration of Al/polymer/ITO were constructed from these polyimides by using conventional solution coating process. The memory devices based on PI-a, PI-b and PI-c exhibited a flash type memory capability, whereas the PI-d presented a write once read many times (WORM) memory capability.
- Zhao, Jing,Peng, Ling,Zhu, Ya-Liang,Song, Yang-Jun,Wang, Li-Jun,Shen, Ying-Zhong
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- Synthesis and fluorescence properties of 3,6-diaminocarbazole-modified pyrrolidinyl peptide nucleic acid
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This work aims to explore a new clickable carbazole-based fluorescent label, its incorporation into pyrrolidinyl peptide nucleic acid (acpcPNA), and the interactions between the labeled PNA probe and DNA by fluorescence spectrophotometry and molecular dynamics simulation. A carbazole derivative, namely 3,6-diaminocarbazole (DAC), was synthesized and incorporated into the internal and terminal positions of azide-modified acpcPNA via a sequential reductive alkylation and click reaction previously developed by our group. The DAC-modified acpcPNA can form a stable hybrid with complementary DNA with somewhat lower stability compared to unmodified acpcPNA. Most importantly, the DAC-modified acpcPNA exhibits a remarkable fluorescence increase in the presence of DNA (up to 35.5 fold with complementary DNA). Non-complementary as well as single mismatched DNA targets gave a smaller fluorescence increase (1.1 to 18.6 fold), and the discrimination could be further improved by increasing the temperature to dissociate the mismatched hybrids. Molecular dynamic simulations revealed that the DAC interacts with adjacent nucleobases in single stranded PNA, resulting in quenching of the fluorescence signal. When the PNA formed a hybrid with DNA, the DAC was pushed away from the duplex, resulting in a fluorescence increase. Thus, the DAC-labeled acpcPNA is a potential candidate as a self-reporting probe for determination of DNA sequences.
- Dangsopon, Aukkrapon,Poomsuk, Nattawee,Siriwong, Khatcharin,Vilaivan, Tirayut,Suparpprom, Chaturong
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- Disubstituted 1,8-dipyrazolcarbazole derivatives as a new type of c-myc G-quadruplex binding ligands
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A series of 1,8-dipyrazolcarbazole (DPC) derivatives (6a-6d, 7a-7d) designed as G-quadruplex ligands have been synthesized and characterized. The FRET-melting and SPR results showed that the DPC derivatives could well recognize G-quadruplex with strong discrimination against the duplex DNA. In addition, the DPC derivatives showed much stronger stabilization activities and binding affinities for c-myc G-quadruplex rather than telomeric G-quadruplex. Therefore, their interactions with c-myc G-quadruplex were further explored by means of CD spectroscopy, PCR-stop assay, and molecular modeling. In cellular studies, all compounds showed strong cytotoxicity against cancer cells, while weak cytotoxicity towards normal cells. RT-PCR assay showed that compound 7b could down-regulate c-myc gene expression in Ramos cell line, while had no effect on c-myc expression in CA46 cell line with NHE III1 element removed, indicating its effective binding with G-quadruplex on c-myc oncogene in vivo.
- Chen, Wei-Jia,Zhou, Chen-Xi,Yao, Pei-Fen,Wang, Xiao-Xiao,Tan, Jia-Heng,Li, Ding,Ou, Tian-Miao,Gu, Lian-Quan,Huang, Zhi-Shu
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- Square [5]molecular necklace formed from cucurbit[8]uril and carbazole derivative
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The formation of square 5-member molecular necklace ([5]MN) is presented by utilizing the host-guest recognition-driven self-assembly between CB[8] and carbazole derivative 1·2Cl-, which bears two 4,4′-bipyridin-1-ium (BP) arms with a orthogonal geometry. The self-assembly and stimuli-responsive behaviors of square [5]MN are comprehensively investigated by NMR (1H, COSY, NOSEY, and DOSY), UV-vis, DLS, and SEM methods.
- Li, Jie,Yu, Yang,Luo, Linzhi,Li, Yawen,Wang, Pinpin,Cao, Liping,Wu, Biao
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- Carbazole triamine derivative and preparation method and application thereof
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The invention discloses a carbazole triamine derivative and a preparation method thereof. The carbazole triamine derivative has a structure shown in the following formula. The preparation method of the carbazole triamine derivative is easy to operate, raw materials are easy to obtain, the price is low, the purity is extremely high, and the reaction yield is very high; the carbazole triamine derivative prepared by the method has wide application prospects in the fields of medicine, biology, luminescent materials and the like.
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Paragraph 0070; 0075-0078
(2021/08/06)
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- Diversity of metal-organic macrocycles assembled from carbazole based ligands with different lengths
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A series of carbazole based ligands with different lengths were assembled with nickel ions to construct metal-organic macrocycles. High-resolution mass spectrometry and ion mobility-mass spectrometry have been used to analyse the resulting MnLn assembly coexisting in solution. Combining with the structural analysis of their solid confirmation, it was revealed that the diversity of the metal-organic macrocycles was increased with the flexibility of the ligands.
- Yu, Hao,Wang, Jing,Guo, Xiangyang,Zhang, Rong,He, Cheng,Duan, Chunying
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supporting information
p. 4040 - 4044
(2018/03/26)
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- Carbazole as Linker for Dinuclear Gadolinium-Based MRI Contrast Agents
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Ligands able to complex two gadolinium ions have been synthesized and characterized in view of the ability of the complexes to increase the spin relaxation of water protons. All ligands are based on the heptadentate diethylenetriaminetetraacetic acid (DTTA) chelator and carbazole as a rigid linker. Depending on the derivatization on the nitrogen atom of the five-membered ring, the compounds form small aggregates in aqueous solution, self-assemble to form micelles or bind to human serum albumin. In all cases, this leads to a marked increase in 1H relaxivity at nuclear Larmor frequencies between 20 and 60 MHz. Water exchange on the gadolinium ions as measured by 17O NMR relaxation is fast enough not to limit relaxivity. 1H nuclear magnetic relaxation dispersion profiles were also measured and analyzed using Solomon–Bloembergen–Morgan theory including Lipari–Szabo treatment to include internal motion or anisotropic rotation.
- Mousavi, Bibimaryam,Chauvin, Anne-Sophie,Moriggi, Lo?ck,Helm, Lothar
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p. 5403 - 5412
(2017/12/18)
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- 9-(2'-aryl benzyl)-3, 6-diamino carbazole compound and preparation method thereof
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The invention provides a 9-(2'-aryl benzyl)-3, 6-diamino carbazole compound and a preparation method thereof. The compound is obtained by the following steps: firstly performing nitrification for carbazole, allowing a nitrification product to react with bromobenzyl bromide, adding a reducing agent to generate 9-(2'-bromobenzyl)-3,6-diamino carbazole, and finally allowing 9-(2'-bromobenzyl)-3,6-diamino carbazole to perform Suzuki reaction with various conjugated arylboronic acids to obtain the compound. The compound is simple in synthetic procedures and high in yield; an asymmetric structure is formed by introducing large aromatic side groups by virtue of Suzuki reaction, the regularity of a monomer is destroyed, and when the diamino monomer is polymerized with an anhydride monomer to form a polymer, the polymer is arranged in a non-coplanar manner by virtue of the large aromatic side groups, so that the solubility and optical properties of a synthetic material can be improved.
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Page/Page column 0032; 0039; 0040; 0041; 0042
(2016/10/07)
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- Novel functional triamine monomer containing carbazole structure and preparation method and application thereof
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The invention discloses a novel functional triamine monomer containing a carbazole structure and a preparation method and application thereof. Starting from carbazole, the novel functional triamine monomer containing carbazole is prepared through a nitration reaction, a Ullmann coupling reaction, a reduction reaction and other reactions; or starting from mono-halogenated carbazole or dihalogenated carbazole, the novel functional triamine monomer containing carbazole is prepared through a Ullmann coupling reaction, a Suzuki reaction, a reduction reaction and other reactions. The novel functional triamine monomer containing carbazole is simple in synthesis method and technology, high in yield and easy to purify, and therefore the novel functional triamine monomer containing carbazole is suitable for industrial production. The novel functional triamine monomer can be used for synthesizing hyperbranched and functional polyamide, polyimide, polyamide imide, polyester imide and other polymers.
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Paragraph 0032; 0033; 0034
(2016/10/09)
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- Synthesis, characterization and pharmacological evaluation of some novel 3,6-dinitrocarbazole derivatives
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N-Mannich bases of newly synthesized carbazole compounds were synthesized from carbazole by reacting with series of aldehydes i.e., formaldehyde and acetaldehyde and the various secondary amines. Synthesized compounds were characterized by spectral studies and evaluated for antibacterial activities by cup and plate method. The statistical analysis was done by students t test and the values were expressed as mean ± SEM.
- Tiwari, Ravi,Chhabra, Gurmeet
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experimental part
p. 5987 - 5992
(2010/11/19)
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- Preparation and study of 1,8-di(pyrid-2′-yl)carbazoles
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(Figure Presented) A series of three derivatives of 1,8-di(pyrid-2′- yl)carbazole were prepared by Stille-type coupling of 2-(tri-n-butylstannyl) pyridine with the appropriate 1,8-dibromocarbazole. The carbazoles were prepared by appropriate substitution methodologies on the parent carbazole or by palladium-catalyzed cyclization of di-(p-tolyl)amine to provide the carbazole ring system. An X-ray structure of the di-tert-butyl derivative confirmed that both pyridyl groups were oriented for favorable intramolecular H-bonding to the central N-H. Two orientations of the molecule were found in the unit cell and this observation was corroborated by two N-H stretching bands in the solid state IR. Substitution of N-H by N-D led to increased emission intensity through diminished intramolecular deactivation of the excited state. The di-tert-butyl derivative formed a tridentate complex with Pd(II), which showed a red-shifted band attributed to an intraligand charge transfer state.
- Mudadu, Maria S.,Singh, Ajay N.,Thummel, Randolph P.
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p. 6513 - 6520
(2008/12/22)
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- Chemical uncouplers for the treatment of obesity
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This invention relates to chemical uncouplers with a broader safety window making the use of them in treating obesity and, consequently, in the treatment of obesity related diseases and conditions such as atherosclerosis, hypertension, diabetes, especially type 2 diabetes (NIDDM (non-insulin dependent diabetes mellitus)), impaired glucose tolerance, dyslipidemia, coronary heart disease, gallbladder disease, osteoarthritis and various types of cancer such as endometrial, breast, prostate and colon cancers and the risk for premature death as well as other conditions, such as diseases and disorders, which conditions are improved by an increase in mitochondrial respiration, more attractive.
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- Lithiation of pivaloylamino derivatives of dibenzofuran and 9-methylcarbazole
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2-, 3- and 4-Pivaloylamino derivatives of dibenzofuran [compounds (5), (4) and (6), respectively] and analogous 3-, 2- and 1-substituted derivatives of 9-methylcarbazole [compounds (8), (7) and (9), respectively] were subjected to lithiation at 0°C and subsequent reaction with dimethylformamide. Aldehyde formation took place at positions α to δ to the heteroatom as follows: α for (4) and (7); δ for (5); δ and β (3 : 1) for (8); and α′ (6). No formylation occurred with (9).
- Deady,Sette
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p. 177 - 180
(2007/10/03)
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- Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids
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Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO3/H+) and neutral conditions (Cu(NO3)2; ceric ammonium nitrate) are discussed. A complete 1H and 13C-nmr characterization including ms and also uv absorption spectra in neutral and acid media is presented. A detailed ei-ms and ld-tof-ms study is enclosed because the nitro-β-carbolines constitute a new family of β-carboline-like chromophores with potential use as matrix in uv-maldi-tof-ms.
- Ponce,Erra-Balsells
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p. 1071 - 1082
(2007/10/03)
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- A new method of nitration of carbazoles using ceric ammonium nitrate (CAN)
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A convenient procedure for the mononitration of carbazole and 9-alkylcarbazoles using CAN in CH3CN in presence of SiO2 is reported. The results with 9-acetyl, 9-benzoyl and 9- benzenesulphonylcarbazoles are also discussed.
- Chakrabarty,Batabyal
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