- Synthesis and Characterization of Compounds Based on Carbazole and Sulfone Groups
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Two compounds containing carbazole and sulfone groups with different alkyl chain lengths have been designed and synthesized. The sulfone group has strong absorption characteristics and the alkoxy chain and carbazole group are electron-rich, forming D-δ-A-type symmetrical molecules. The molecules have the characteristics of charge transfer and high thermal stability, and the molecules stack to form a layered staggered stack, reducing the intermolecular π–π interactions. The target compounds also exhibit strong ultraviolet-fluorescent emission in the solid state at room temperature, and they are expected to be good luminescent materials. Graphical Abstract: [Figure not available: see fulltext.]
- Jia, Huixian,Feng, Chenghong,Han, Wanfei,Xue, Yan,Jin, Yanren,Li, Dongfeng
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p. 267 - 274
(2021/11/17)
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- Design, Synthesis, and Pharmacological Characterization of Carbazole Based Dopamine Agonists as Potential Symptomatic and Neuroprotective Therapeutic Agents for Parkinson's Disease
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We have developed a series of carbazole-derived compounds based on our hybrid D2/D3 agonist template to design multifunctional compounds for the symptomatic and disease-modifying treatment of Parkinson's disease (PD). The lead molecules (-)-11b (D-636), (-)-15a (D-653), and (-)-15c (D-656) exhibited high affinity for both D2 and D3 receptors and in GTPγS functional assay, the compounds showed potent agonist activity at both D2 and D3 receptors (EC50 (GTPγS); D2 = 48.7 nM, D3 = 0.96 nM for 11b, D2 = 0.87 nM, D3 = 0.23 nM for 15a and D2 = 2.29 nM, D3 = 0.22 nM for 15c). In an animal model of PD, the test compounds exhibited potent in vivo activity in reversing hypolocomotion in reserpinized rats with a long duration of action compared to the reference drug ropinirole. In a cellular antioxidant assay, compounds (-)-11b, (-)-15a, and (-)-15c exhibited potent activity in reducing oxidative stress induced by neurotoxin 6-hydroxydopamine (6-OHDA). Also, in a cell-based PD neuroprotection model, these lead compounds significantly increased cell survival from toxicity of 6-OHDA, thereby producing a neuroprotective effect. Additionally, compounds (-)-11b and (-)-15a inhibited aggregation and reduced toxicity of recombinant alpha synuclein protein in a cell based in vitro assay. These observations suggest that the lead carbazole-based dopamine agonists may be promising multifunctional molecules for a viable symptomatic and disease-modifying therapy of PD and should be further investigated.
- Elmabruk, Asma,Das, Banibrata,Yedlapudi, Deepthi,Xu, Liping,Antonio, Tamara,Reith, Maarten E. A.,Dutta, Aloke K.
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p. 396 - 411
(2019/01/24)
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- A organic long afterglow compound and its preparation method and application (by machine translation)
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The invention relates to a kind of organic long afterglow compound and its preparation method and application, the organic long afterglow compounds have the formula (I) indicated by the structure, the present invention provides compounds of formula (I) have shown long afterglow compound long service life, and different structure sub compound of different service life, various colors, when the stop of the excitation light source is illuminated, its emitted light by the fluorescence can be realized to the phosphorescent color change, after gradually reducing the brightness, the nature of the time-resolved technology can be combined with the four-dimensional coding, a large amount of information storage and information encryption. (by machine translation)
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Paragraph 0089; 0091-0094
(2019/10/23)
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- METHODS AND COMPOSITIONS FOR THE TREATMENT OF RNA VIRAL INFECTIONS
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Disclosed herein, inter alia, are agents having antiviral activity and methods of use thereof.
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- Highly uniform supramolecular nano-films derived from carbazole-containing perylene diimide: Via surface-supported self-assembly and their electrically bistable memory behavior
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For electrical memory applications, two perylenetetracarboxylic diimide (PDI) derivatives, N,N′-(6-carbazole hexyl)-1,7-di(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic diimide (PDI-6Cz) and N,N′-(2-carbazole ethyl)-1,7-di(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic diimide (PDI-2Cz), were synthesized and their surface-supported self-assembly behaviors were investigated. PDI-2Cz tends to self-organize into regular rods, which are proved to be hexagonal lattices with single crystal nature, based on which memory device fabrication and electrically bistable behavior evaluation are technically infeasible. Whereas PDI-6Cz readily self-assembles into highly uniform nano-films with a considerably smooth surface, in which the X-ray diffraction study indicates strong π-π stacking between the aromatic skeletons. Further characterization indicates that sandwich memory devices using a PDI-6Cz nano-film as the active layer exhibit reprogrammable flash-type memory behavior with a switching-on voltage of ca. 0.8 V and an ON/OFF current ratio of 104. Besides, the devices exhibit excellent long-term operation stability, enduring up to 108 reading cycles without obvious current variation and an ultrafast switching response period of less than 20 ns. Photophysical and electrochemical measurements and DFT molecular simulations were conducted to determine the electronic transition occurring in the supramolecular self-assembled nano-film. Compared with organic storage materials based on polymers, the current memory device exhibits lower threshold voltage and more rapid response speed, which provides a new way for developing high-performance organic data storage materials.
- Khan, Qudrat Ullah,Tian, Guofeng,Bao, Lin,Qi, Shengli,Wu, Dezhen
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supporting information
p. 11506 - 11515
(2018/07/25)
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- External Heavy-Atom Effect via Orbital Interactions Revealed by Single-Crystal X-ray Diffraction
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Enhanced spin-orbit coupling through external heavy-atom effect (EHE) has been routinely used to induce room-temperature phosphorescence (RTP) for purely organic molecular materials. Therefore, understanding the nature of EHE, i.e., the specific orbital interactions between the external heavy atom and the luminophore, is of essential importance in molecular design. For organic systems, halogens (e.g., Cl, Br, and I) are the most commonly seen heavy atoms serving to realize the EHE-related RTP. In this report, we conduct an investigation on how heavy-atom perturbers and aromatic luminophores interact on the basis of data obtained from crystallography. We synthesized two classes of molecular systems including N-haloalkyl-substituted carbazoles and quinolinium halides, where the luminescent molecules are considered as "base" or "acid" relative to the heavy-atom perturbers, respectively. We propose that electron donation from a π molecular orbital (MO) of the carbazole to the σ? MO of the C-X bond (π/σ?) and n electron donation to a π? MO of the quinolinium moiety (n/π ?) are responsible for the EHE (RTP) in the solid state, respectively.
- Sun, Xingxing,Zhang, Baicheng,Li, Xinyang,Trindle, Carl O.,Zhang, Guoqing
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p. 5791 - 5797
(2016/08/05)
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- Bipolar blue phosphorescent host material based on carbazole and 1,2,4-triazole
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The invention discloses a bipolar blue phosphorescent host material which is as shown in a structural general formula (I) and takes carbazole and 1,2,4-triazole as a donor and a receptor respectively. The triplet-state energy level of the host material is
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Paragraph 0055
(2016/12/22)
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- A chirality alkali fluorescent probe compound and its preparation
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The invention discloses a Schiff base type fluorescent probe compound and a preparation method thereof. The Schiff base type fluorescent probe compound has a structure as shown in formula (I) in the specification and is characterized by comprising the following steps: (1) preparing a Rhodamine B-hydrazide compound; (2) preparing 9-bromoethyl carbazole; (3) preparing 3-formyl-9 ethyl carbazole; (4) synthesizing a Schiff base type fluorescent compound, wherein the synthesized Schiff base type fluorescent compound has ''C=N'' bonds, and the prepared compound has a large ''Pi'' conjugate plane aromatic ring structure and is good in fluorescence property; structurally, lone pair electrons and heterocyclic atoms such as O and N exist on the C=N, so the compound has a potential application in detection of metal ions in cells.
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Paragraph 0025; 0031
(2017/05/23)
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- Carbazole-based gold(i) complexes with alkyl chains of different lengths: Tunable solid-state fluorescence, aggregation-induced emission (AIE), and reversible mechanochromism characteristics
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In this paper, seven carbazole-based mononuclear gold(i) complexes with alkyl chains of different lengths have been synthesized and reported. All of these gold(i) complexes exhibit outstanding AIE characteristics. Furthermore, these various solid-state light-emitting AIE-active gold(i) complexes all show reversible mechanochromic fluorescent behaviors. The possible mechanism explaining these interesting AIE and mechanochromism phenomena involves a variation in weak multiple intermolecular C-H...F and π...π interactions and the formation or alteration of aurophilic interactions.
- Chen, Zhao,Yang, Lan,Hu, Yuxuan,Wu, Di,Yin, Jun,Yu, Guang-Ao,Liu, Sheng Hua
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p. 93757 - 93764
(2015/11/17)
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- Adjustment of conformation change and charge trapping in ion-doped polymers to achieve ternary memory performance
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Ion-doped poly(4-vinylpyridine) derivatives (P4VPCz), where in the pendant chains the electron-withdrawing pyridine moiety and acceptor carbazole moiety are linked by a flexible alkyl spacer were designed and synthesized. Sandwiched ITO/P4VPCz/Al devices, made through simple spin-coating processes have shown that they could be tuned from a binary to ternary memory performance, by increasing the carbazole content. P4VPCz2 with a 20% mole ratio of the carbazole moiety shows a binary performance according to the charge trapping of the pyridine acceptor in the polymer, while P4VPCz5 which contains a 50% mole ratio of carbazole in the pendant chains, exhibits a ternary data storage ability, probably induced by double mechanisms (i.e. a conformational change and charge trapping). Interestingly, as the carbazole mole ratio reached 80%, the polymer P4VPCz8 has a high conductivity state, with no switching behavior, because of the large amount of doped ions improving the charge transfer mobility. Thus, we hope can offer a guideline to achieve a high-performance multilevel memory material, via combining different mechanisms as well as doping ions.
- He, Dongwei,Zhuang, Hao,Liu, Haifeng,Liu, Hongzhang,Li, Hua,Lu, Jianmei
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p. 7883 - 7889
(2013/12/04)
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- A single-layer approach to electrochromic materials
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This study is focused on the development of electrochromic (EC) materials that could be incorporated into electrically-driven switchable devices such as electrochromogenic glasses. The ultimate goal of this research is to depart from the complexity of the EC device construction which is in use today. Such construction consists of three layers each of them incorporating a specific functionality: the electrochromophore, the electrolyte and the ion storage, assembled between two transparent or reflective electrodes. In most of these conventional devices the electrolyte layer is a liquid or a gel. Since solid-state EC devices are of high commercial interest, we are exploring various avenues to reduce the number of layers to one layer that is all-solid and electrochromically/electrolytically and ionically functional. The design strategy is based on the use of polymers such as poly(epichlorohydrin-co- ethylene oxide), poly(vinyl butyral) and poly(ethylene-co-methacrylic acid) ionomer, to which EC properties were introduced by grafting reactions with specifically synthesized carbazole derivatives. A combination of analytical techniques was used to characterize the monomers and the carbazole-grafted polymers. A proof of concept was demonstrated for a single-layer, all-solid-state EC device consisting of a film of poly(ECH-co-EO) containing pendent carbazole groups, assembled between two transparent electrodes, Sn-doped In2O3 oxide-coated glasses.
- Percec, Simona,Tilford, Susan
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scheme or table
p. 361 - 368
(2012/01/12)
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- Conjugated polymer network films from precursor polymers: Electrocopolymerization of a binary electroactive monomer composition
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We report the synthesis and electropolymerization of a precursor polymer with a binary molecular composition of thiophene and carbazole electroactive groups to form ultrathin films of conjugated polymer networks (CPN) on flat indium tin oxide (ITO) substrates. In the past we have demonstrated the precursor polymer approach based on a single pendant electroactive group. In this work, we describe the interesting electrocopolymerization mechanism and properties of precursor polymers prepared with two different types of pendant electroactive groups (statistical copolymer) and compared behavior to their respective homopolymers. The presence of a smaller amount of carbazole induces the electropolymerization of the higher oxidation potential thiophene units via the reaction of a radical cation and a neutral molecule pathway. These electrochemically generated thin films gave unique optical, electrochemical, and morphological properties as a function of composition. The film properties were investigated by cyclic voltammetry (CV), spectroelectrochemistry, EQCM, atomic force microscopy (AFM), and X-ray photoelectron spectroscopy (XPS).
- Taranekar, Prasad,Baba, Akira,Fulghum, Timothy M.,Advincula, Rigoberto
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p. 3679 - 3687
(2008/02/01)
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- Combined phase transfer catalysis and ultrasound to enhance tandem alkylation of azo dyes
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Ultrasound has been found to enhance N-substitution against elimination in the reaction of carbazole-containing bromides 3 with a Disperse Orange 3 derivative 2 under PTC condition. Upon using combined PTC and ultrasound conditions, a series of bifunctional molecules 1 have been prepared to possess charge-transporting agents and nonlinear optical chromophores in 2:1 ratio.
- Li, Xiang,Wang, Jie,Mason, Richard,Bu, Xiu R,Harrison, Joycelyn
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p. 3747 - 3753
(2007/10/03)
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