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Heterometallic Actinide-Containing Photoresponsive Metal-Organic Frameworks: Dynamic and Static Tuning of Electronic Properties
Acquiring fundamental knowledge of properties of actinide-based materials is a necessary step to create new possibilities for addressing the current challenges in the nuclear energy and nuclear waste sectors. In this report, we established a photophysics–electronics correlation for actinide-containing metal-organic frameworks (An-MOFs) as a function of excitation wavelength, for the first time. A stepwise approach for dynamically modulating electronic properties was applied for the first time towards actinide-based heterometallic MOFs through integration of photochromic linkers. Optical cycling, modeling of density of states near the Fermi edge, conductivity measurements, and photoisomerization kinetics were employed to shed light on the process of tailoring optoelectronic properties of An-MOFs. Furthermore, the first photochromic MOF-based field-effect transistor, in which the field-effect response could be changed through light exposure, was constructed. As a demonstration, the change in current upon light exposure was sufficient to operate a two-LED fail-safe indicator circuit.
Martin, Corey R.,Leith, Gabrielle A.,Kittikhunnatham, Preecha,Park, Kyoung Chul,Ejegbavwo, Otega A.,Mathur, Abhijai,Callahan, Cameron R.,Desmond, Shelby L.,Keener, Myles R.,Ahmed, Fiaz,Pandey, Shubham,Smith, Mark D.,Phillpot, Simon R.,Greytak, Andrew B.,Shustova, Natalia B.
p. 8072 - 8080
(2021)
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A Metal-Free Direct Arene C?H Amination
The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).
Wang, Tao,Hoffmann, Marvin,Dreuw, Andreas,Hasagi?, Edina,Hu, Chao,Stein, Philipp M.,Witzel, Sina,Shi, Hongwei,Yang, Yangyang,Rudolph, Matthias,Stuck, Fabian,Rominger, Frank,Kerscher, Marion,Comba, Peter,Hashmi, A. Stephen K.
supporting information
p. 2783 - 2795
(2021/04/05)

Bicyclic Phenyl–Ethynyl Architectures: Synthesis of a 1,4-Bis(phenylbuta-1,3-diyn-1-yl) Benzene Banister
The novel diacetylene bridged terphenylic macrocycle 1 is presented and discussed in the context of rotationally restricted “Gel?nder” oligomers. The 1,4-bis(phenylbuta-1,3-diyn-1-yl) benzene bridge of diacetylene 1 is significantly longer than its terphenyl backbone, forcing the bridge to bend around the central pylon. The synthesis of molecule 1 is based to a large extent on acetylene scaffolding strategies, profiting from orthogonal alkyne protection groups to close both macrocyclic subunits by oxidative acetylene coupling sequentially. The spatial arrangement and the dynamic enantiomerization process of the bicyclic target structure 1 are analyzed. In-depth NMR investigations not only reveal an unexpected spatial arrangement with both oligomer strands bent alongside the backbone, but also display the limited stability of the model compound in the presence of molecular oxygen.
Bannwart, Linda Maria,Müntener, Thomas,Rickhaus, Michel,Jundt, Lukas,H?ussinger, Daniel,Mayor, Marcel
supporting information
p. 6295 - 6307
(2021/03/08)

Method for reducing aromatic nitro into arylamine
The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
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Paragraph 0109-0112; 0213-0216

(2020/07/15)

CO-free, aqueous mediated, instant and selective reduction of nitrobenzeneviarobustly stable chalcogen stabilised iron carbonyl clusters (Fe3E2(CO)9, E = S, Se, Te)
Highly stable and thermally robust iron chalcogenide carbonyl clusters Fe3E2(CO)9(E = S, Se or Te) have been explored for the reduction of nitrobenzene. A 15 min thermal heating of an aqueous solution of nitrobenzene and hydrazine hydrate in the catalytic presence of Fe3E2(CO)9(E = S, Se or Te) clusters yield average to excellent aniline transformations. Among the S, Se and Te based iron chalcogenised carbonyl clusters, the diselenide cluster was found to be most efficient and produce almost 90% yield of the desired amino product, the disulfide cluster was also found to be significantly active, produce the 85% yield of amino product, while the ditelluride cluster was not found to be active and produced only 49% yield of the desired product. The catalyst can be reused up to three catalytic cycles and it needs to be dried in an oven for one hour prior to reuse for the best results. The developed method is inexpensive, environmentally benign, does not require any precious metal or a high pressure of toxic CO gas and exclusively brings the selective reduction of the nitro group under feasible and inert free conditions.
Joshi, Raj Kumar,Kumari, Sangeeta,Sharma, Charu,Soni, Aditi,Srivastava, Avinash Kumar
p. 32516 - 32521
(2020/09/17)

Aromatic C-H amination in hexafluoroisopropanol
We report a direct radical aromatic amination reaction that provides unprotected anilines with an improvement in the substrate scope compared to prior art. Hydrogen bonding by the solvent hexafluoroisopropanol to anions of cationic species is responsible for increased reactivity and can rationalize the enhancement in substrate scope. Our findings may have bearings on radical additions to arenes for direct C-H functionalization in general.
D'Amato, Erica M.,B?rgel, Jonas,Ritter, Tobias
p. 2424 - 2428
(2019/02/28)

Method for synthesizing dibromobenzene -2,5- 1,4- diiodo benzene (by machine translation)
The synthetic method disclosed by the invention comprises 1,4 - the following steps: the, synthesis method disclosed by. the, invention has a good industrial production prospect, 1,4 - in the prior, art that, the raw materials are firstly, 2,5 - subjected to a nitrification step and then subjected to 2,5 - an iodine, generation step to generate 2,5 - the second bromo,4-diiodo benzene 1,4 . (by machine translation)
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(2020/01/12)

Synthetic method of 2,5-dibromo-p-phenylenediamine
The invention discloses a synthetic method of 2,5-dibromo-p-phenylenediamine. According to the method, the 2,5-dibromo-p-phenylenediamine is synthesized from a compound shown as I, namely, p-dibromobenzene serving as a starting material. By adopting the synthetic method of the 2,5-dibromo-p-phenylenediamine disclosed by the invention, the 2,5-dibromo-p-phenylenediamine can be effectively synthesized. Moreover, the synthetic method has the advantages of high synthesis efficiency, safe production, simple process operation, short production period and the like, so that the method is more suitablefor large-scale and industrialized production of the 2,5-dibromo-p-phenylenediamine.
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(2018/10/26)

Cu-catalyzed reduction of azaarenes and nitroaromatics with diboronic acid as reductant
A ligand-free copper-catalyzed reduction of azaarenes with diboronic acid as reductant in an aprotic solvent under mild conditions has been developed. Most interestingly, the nitroazaarenes could be reduced exclusively to give the corresponding amines without touching the azaarene moieties. Furthermore, the reductive amination of aromatic nitro compounds and aromatic aldehydes has also been realized. A series of hydrogenated azaarenes and secondary amines were obtained with good functional group tolerance.
Pi, Danwei,Zhou, Haifeng,Zhou, Yanmei,Liu, Qixing,He, Renke,Shen, Guanshuo,Uozumi, Yasuhiro
p. 2121 - 2129
(2018/03/23)

Functional phenylethynylene side arm poly(arylene ethynylene) conjugated polymers: Optical and electrochemical behavior for enrichment of electronic applications
The poly(arylene ethynylene) (PAE) conjugated polymers (CPs) with a donor-acceptor (D-A) side arm have been designed and synthesized using Sonogashira cross coupling in the presence of cyano methylene, or cyano thiophene gave diethynyl (A) and alkoxy and alkyl substituted diiodo aryl monomers (D). An interesting electronic response in optical measurements such as UV-visible (UV-vis) and fluorescence (FL) spectra was observed in tetrahydrofuran solvent. From the FL spectra, it was observed that the CP solutions possess an interesting long bathochromic shift when compared with the UV-vis spectra, because of the electron withdrawing, electron releasing and conjugation effects. The electrochemical and thin film UV-vis spectral measurements provided highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) electronic energy levels and their corresponding semiconducting electronic energy gaps (Eg) of the PAE CPs. Among the side arm CPs, polymers P1 and P5 have low Eg of 2.14 eV and 2.17 eV. The new PAE CPs are reliable for use in electronic and photonics applications.
Arun Kumar,Gomathi Priya,Alagar
supporting information
p. 5767 - 5773
(2018/04/23)

Metal-free Reduction of Nitro Aromatics to Amines with B 2 (OH) 4 /H 2 O
A metal-free reduction of nitro aromatics mediated by diboronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.
Chen, Danyi,Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Liu, Qixing,Zhang, Kaili,Uozumi, Yasuhiro
supporting information
p. 1765 - 1768
(2018/06/26)

Flipping the Switch: Fast Photoisomerization in a Confined Environment
Stimuli-responsive materials are vital for addressing emerging demands in the advanced technology sector as well as current industrial challenges. Here, we report for the first time that coordinative integration of photoresponsive building blocks possessing photochromic spiropyran and diarylethene moieties within a rigid scaffold of metal-organic frameworks (MOFs) could control photophysics, in particular, cycloreversion kinetics, with a level of control that is not accessible in the solid state or solution. On the series of photoactive materials, we demonstrated for the first time that photoisomerization rates of photochromic compounds could be tuned within almost 2 orders of magnitude. Moreover, cycloreversion rates of photoresponsive derivatives could be modulated as a function of the framework structure. Furthermore, through MOF engineering we were able to achieve complete isomerization for coordinatively immobilized spiropyran derivatives, typically exhibiting limited photoswitching behavior in the solid state. For instance, spectroscopic analysis revealed that the novel monosubstituted spiropyran derivative grafted to the backbone of the MOF pillar exhibits a remarkable photoisomerization rate of 0.16 s-1, typical for cycloreversion in solution. We also applied the acquired fundamental principles toward mapping of changes in material properties, which could provide a pathway for monitoring material aging or structural deterioration.
Williams, Derek E.,Martin, Corey R.,Dolgopolova, Ekaterina A.,Swifton, Anton,Godfrey, Danielle C.,Ejegbavwo, Otega A.,Pellechia, Perry J.,Smith, Mark D.,Shustova, Natalia B.
supporting information
p. 7611 - 7622
(2018/06/06)

Stabilisation of gold nanoparticles by N-heterocyclic thiones
Gold nanoparticles (Au-NPs) have been prepared using N-heterocyclic thiones (NHTs) as ligand stabilisers. These Au-NPs have been shown to be very stable, even in air, and have been characterized by a combination of several techniques (TEM, HR-TEM, STEM-HAADF, EDX, DLS, elemental analysis and 1H NMR). These nanoparticles are active in the catalytic reduction of nitroarenes to anilines.
Moraes, Leonardo C.,Lacroix, Bertrand,Figueiredo, Rute C.,Lara, Patricia,Rojo, Javier,Conejero, Salvador
supporting information
p. 8367 - 8371
(2017/07/12)

A compound 5, 8 - II (3, 4 - ethylene dioxy thienyl) - quinoline synthesis method
The invention discloses a synthetic method of 5,8-bi(3,4-ethylenedioxy thienyl)-quinoline. The method comprises the steps of with 3,4-ethylenedioxy thienyl (EDOT) and p-dibromobenzene as substrates, brominating hydrogen at the position 2 of EDOT by using N-bromosuccinimide in the presence of tetrahydrofuran and acetic acid; performing nitrification on p-dibromobenzene, and performing Skraup reaction on a product obtained through reduction to generate 5,8-dibromo quinoline; enabling a product obtained by performing Grignard reaction on brominated EDOT to react with 5,8-dibromo quinoline under the catalytic action of nickel chloride to generate 5,8-bi(3,4-EDOT)-quinoline; performing electrochemical characterization of dyeing properties of the product. The synthetic method is simple and feasible, and has industrial prospects.
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(2017/07/04)

Carbonyl Iron Powder: A Reagent for Nitro Group Reductions under Aqueous Micellar Catalysis Conditions
An especially mild, safe, efficient, and environmentally responsible reduction of aromatic and heteroaromatic nitro-group-containing educts is reported that utilizes very inexpensive carbonyl iron powder (CIP), a highly active commercial grade of iron powder. These reductions are conducted in the presence of nanomicelles composed of TPGS-750-M in water, a recyclable aqueous micellar reaction medium. This new technology also shows broad scope and scalability and presents opportunities for multistep one-pot sequences involving this reducing agent.
Lee, Nicholas R.,Bikovtseva, Agata A.,Cortes-Clerget, Margery,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information
p. 6518 - 6521
(2017/12/26)

Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid
An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.
Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Pi, Danwei,Shen, Guanshuo
p. 3898 - 3904
(2017/06/13)

One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.
Zhao, Fen,Chen, Zhen,Xie, Kai,Yang, Rui,Jiang, Yu-Bo
p. 109 - 113
(2016/01/25)

Polymer-based fluorescence sensor incorporating thiazole moiety for direct and visual detection of Hg2+ and Ag+
A thiazole-based conjugated polymer was synthesized by the polymerization reaction of 4,7-dibromo-2-methylbenzo[d]thiazole with 1,4-diethynyl-2,5-bis(octyloxy)benzene via Pd-catalyzed Sonogashira coupling reaction. The conjugated polymer emits bright green fluorescence and exhibits 'turn-off' fluorescent quenching responses towards both Hg2+ and Ag+ over other cations, such as Li+, K+, Ca2+, Mg2+, Ba2+, Zn2+, Cd2+, Co2+, Ni2+, Pb2+, Cu2+, Al3+ and Fe3+. More importantly, the color change of this polymer solution could be clearly observed by the naked eyes upon the addition of Hg2+ (green to colorless) and Ag+ (green to yellow), indicating that this thiazole-based conjugated polymer material could be used as a colorimetric sensor for directly visual detection of Hg2+ and Ag+.
Li, Fei,Meng, Fandian,Wang, Yuxiang,Zhu, Chengjian,Cheng, Yixiang
p. 1700 - 1704
(2015/03/31)

Facile protocol for reduction of nitroarenes using magnetically recoverable CoM0.2Fe1.8O4 (M = Co, Ni, Cu and Zn) ferrite nanocatalysts
Transition metal doped cobalt ferrite (CoM0.2Fe1.8O4 (M = Co, Ni, Cu, Zn)) nanoparticles were fabricated using the sol-gel methodology. The obtained ferrite nanoparticles were annealed at 400 °C and characterized using Fourier transform infra-red spectroscopy (FT-IR), X-ray diffraction (XRD), high resolution transmission electron microscopy (HR-TEM), vibrating sample magnetometry (VSM) and energy dispersive X-ray (EDX) and scanning transmission electron microscopy (STEM). In the FT-IR spectra two bands in the range 1000-400 cm-1 were observed corresponding to the M-O bond in the tetrahedral and octahedral sites. XRD patterns confirmed the formation of a cubic spinel structure with a Fd3m space-group. HR-TEM analysis revealed a quasi-spherical shape with particle sizes in the range 20-30 nm for all the synthesized ferrite nanoparticles. The lattice inter-planar distances of 0.29, 0.25, 0.21 and 0.16 nm obtained from HR-TEM corresponding to the (2 2 0), (3 1 1), (4 0 0) and (5 1 1) lattice planes respectively were in complete agreement with the XRD data. The EDX-STEM confirmed the elemental composition as per the desired stoichiometric ratio. The catalytic efficiency of the synthesized ferrite samples was explored for the reduction of nitrophenols. Cu substituted cobalt ferrite nanoparticles (CoCu0.2Fe1.8O4) possessed excellent catalytic activity while CoM0.2Fe1.8O4 (M = Co, Ni and Zn) were inactive for the same. The substrate scope of the developed protocol was also evaluated for the reduction of various CH3-, NH2-, Br-, Cl- etc. substituted nitroaromatic compounds.
Goyal, Ankita,Kapoor, Surbhi,Samuel, Pankaj,Kumar, Vinod,Singhal, Sonal
p. 51347 - 51363
(2015/06/25)

Trinuclear {Co2+-M3+-Co2+} complexes catalyze reduction of nitro compounds
This work presents synthesis and characterization of trinuclear {Co2+-Co3+-Co2+} and {Co2+-Fe3+-Co2+} complexes with accessible peripheral Co(ii) ions. Both trinuclear complexes function as efficient reusable heterogeneous catalysts for the selective reduction of assorted nitro compounds to the corresponding amines. The mechanistic investigations suggest the involvement of a Co(ii)-Co(i) cycle in the catalysis.
Srivastava, Sumit,Dagur, Manvender S.,Ali, Afsar,Gupta, Rajeev
p. 17453 - 17461
(2015/10/19)

Influence of the benzo[d]thiazole-derived π-bridges on the optical and photovoltaic performance of D-π-A dyes
New metal-free organic sensitizers containing a benzo[d]thiazole or phenyl unit as the π-conjugated system, a triphenylamine as an electron donor, and a cyanoacrylic acid moiety as an electron acceptor were synthesized and used for dye-sensitized solar cells. Photophysical and electrochemical properties of these dyes were investigated, and their performances as sensitizers in solar cells were measured. The introduction of a benzo[d]thiazole unit into the molecular structure resulted in a high incident photon-to-current conversion efficiency (more than 70%) from 340 nm to 600 nm. One solar cell containing a benzo[d]thiazole unit, produced a η of 5.85% (JSC = 10.63 mA cm-2, VOC = 0.72 V, and ff = 0.77) under 100 mW cm -2 simulated AM 1.5 G solar irradiation.
Ci, Zhenhua,Yu, Xiaoqiang,Bao, Ming,Wang, Chaolei,Ma, Tingli
p. 619 - 625
(2013/03/14)

Synthesis of symmetrical dinitro-and diamino-substituted Troeger's base analogues
This report describes a new synthetic approach to symmetrical diamino-substituted Troeger's base analogues, allowing the synthesis of 1,7-, and 4,10-diamino derivatives with no additional substituents and of 3,9-diamino derivative with methyl groups in the 1-, 4-, 7-and 10-positions. The synthesis uses regioselective nitration of dihalo-substituted-or tetrahalo-substituted Troeger's bases followed either by hydrogenation of the nitro functions accompanied by removal of halogen atoms or alternatively by chemoselective reduction of nitro groups to obtain the dihalo-diamino- substituted Troeger's base analogues. The 2,8-diamino derivatives, not accessible by this approach, can be prepared by Buchwald-Hartwig amination of the 2,8-dibromo-substituted Troeger's bases.
Sturala, Jiri,Cibulka, Radek
p. 7066 - 7074
(2013/02/21)

A new class of heterogeneous platinum catalysts for the chemoselective hydrogenation of nitroarenes
A new series of nanostructured platinum catalysts able to catalyze the selective reduction of nitroarenes has been developed. The materials, made of organosilica physically doped with nanostructured platinum(0), are stable and efficient. Reactions in general proceed with high yield and often go to completion, while the catalysts can be reused in further reaction runs. This establishes a new class of relevant solid catalysts for synthetic organic chemistry named SiliaCat Platinum-Hydrogel.
Pandarus, Valerica,Ciriminna, Rosaria,Beland, Francois,Pagliaro, Mario
scheme or table
p. 1306 - 1316
(2011/06/25)

Copper-catalyzed synthesis of azaspirocyclohexadienones from ∝-azido- N -arylamides under an oxygen atmosphere
A copper-catalyzed reaction of ∝-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from ∝-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C-O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O2 was found to be incorporated into the cyclohexadienone moiety.
Chiba, Shunsuke,Zhang, Line,Lee, Jian-Yuan
supporting information; experimental part
p. 7266 - 7267
(2010/08/05)

ALKYL-SUBSTITUTED 3' COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, Ar, m and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 33

(2010/02/17)

CONDENSED HETEROCYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I) wherein R1, A, B, D, E, G, Q, Ar, n, m, and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 94

(2010/04/03)

ACYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, R5, Q, G, Ar, m, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 62

(2010/03/02)

4'-AMINO CYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): formula (I) wherein Cy is selected from formula (Il) and wherein R1, R2, R3, Q, G, Ar, m, n and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 112

(2010/04/06)

PYRROLIDINE-SUBSTITUTED AZAINDOLE COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, A, B, D, E, G, Ar, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 44

(2010/02/17)

Electrophilic bromination of meta-substituted anilines with N-bromosuccinimide: Regioselectivity and solvent effect
N-Bromosuccinimide-mediated electrophilic aromatic bromination of a series of anilines substituted with an electron-with-drawing group in the meta position was investigated. The regioselectivity of the reaction is markedly dependent on the polarity of the solvent and the bromination reaction can be tuned by appropriate selection of the reaction medium. Georg Thieme Verlag Stuttgart.
Bartoli, Sandra,Cipollone, Amalia,Squarcia, Antonella,Madami, Andrea,Fattori, Daniela
experimental part
p. 1305 - 1308
(2009/12/24)

3' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein Q, R1, R4, m and Ar are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 129

(2009/04/25)

Synthesis of terphenyl oligomers as molecular electronic device candidates
Six functionalized bis(phenylene ethynylene)-p,p-terphenyls (BPETs) have been synthesized as potential molecular electronic devices. The molecules containing mono- and dinitro terphenyl cores, were rationally designed based on the electronic properties recently found in oligo(phenylene ethynylene)s (OPEs). From our understanding of the conductance properties in OPEs, improvement of electronic properties may be possible by using BPETs due to a higher rotational barrier between the central aromatic rings of the compounds prepared here. BPETs cores were functionalized with nitro groups and with different metallic adhesion moieties (alligator clips) to provide new compounds for testing in the nanopore and planar testbed structures.
Maya, Francisco,Tour, James M.
p. 81 - 92
(2007/10/03)

Phenylene ethynylene diazonium salts as potential self-assembling molecular devices
(matrix presented) Functionalized diazonium salts for molecular electronic devices are prepared by the reaction of the corresponding anilines with NOBF4 in sulfolane-acetonitrile solvent.
Kosynkin, Dmitry V.,Tour, James M.
p. 993 - 995
(2007/10/03)

Halo-substituted aminobenzenes prepared by Pd-catalyzed amination
The selective monoamination of aryl dihalides by primary amines and polyamines in the presence of the Pd2(dba)3/dppf catalytic system and NaOt- Bu provides a convenient method for the synthesis of aminobenzenes substituted at the ortho, meta, or para position of the aryl ring by a halogen atom. Under these conditions the reaction of polyamine compounds having 1,2-diaminoethane or 1,3-diaminopropane moieties proceeds selectively leading to monoaryl-substituted derivatives of polyamines. Moreover, this is a remarkably efficient method to realize the arylation of a primary amine group of polyamines in the presence of a secondary one.
Beletskaya, Irina P.,Bessmertnykh, Alla G.,Guilard, Roger
p. 1459 - 1461
(2007/10/03)

Imine-bridged planar poly(p-phenylene) derivatives for maximization of extended π-conjugation. The common intermediate approach
Described are two approaches to planar conjugated poly(p-phenylene) (PPP) derivatives. The first approach, involving lactam bridges, was unsuccessful due to the insolubility of the 6(5H)-phenanthridinonyl moieties. The second approach, which utilized imine bridges, worked excellently since the compounds were generally soluble and the bridge formations were highly efficient. The main PPP backbone was synthesized via Pd(0)-catalyzed coupling of an arylbis(boronic ester) with an aryl dibromide. Imine bridges, which are formed by exposure of the polymer to trifluoroacetic acid or HCl, force the consecutive units into planarity. The bridging units are sp2 hybridized, thus allowing for greater π-electron flow between the consecutive phenyl units. The polymers, upon planarization, exhibit enormous bathochromic shifts of 210-240 nm. The optical spectra of the planar systems are compared to that of the parent nonplanarized polymers, oligo(p-phenylenes), and PPP. When the bridges were n-dodecyl- or n-octylphenyl-substituted, the fully planar structures could be made into flexible free-standing films. Additionally, an improved method is described in which a common intermediate, an aryl dibromo diacyl halide, could be used to prepare both the A and B units for the AB-type step growth polymerization. In one case, a selective alkylation or arylation of the acyl portions was accomplished using lower order cyanocuprates or Pd(0)-catalyzed ketone formation. For the second monomer, a bis-Curtius rearrangement, in the presence of tert-butyl alcohol, converted both carbonyl moieties to BOC protected amines.
Lamba, Jaydeep J. S.,Tour, James M.
p. 11723 - 11736
(2007/10/02)

Synthesis of planar poly(p-phenylene) derivatives for maximization of extended π-conjugation
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Tour, James M.,Lamba, Jaydeep J. S.
p. 4935 - 4936
(2007/10/02)

Bromination of anilines in superacids
In HF-SbF5, bromination of aniline at -40 deg C by Br2 ( 0.6 equivalent) yields monobromoderivatives 2a (3percent), 2b (24percent) and 2c (50percent), the electrophile reacting on the anilinium ion.These percentages reflect the relative reactivities in the ortho, meta and para positions, no isomerization occuring either in the intermediate arenium ions or in the products.At room temperature, the products equilibrate (2a/2b/2c: 3/50/47), the process being intramolecular and proceeding by 1,2 Br shifts.Dibromation of aniline (Br2/substrate: 1.2 equivalent) gives compounds 3a (10percent) and 3b (55percent), the second bromination being controlled, in the corresponding anilinium ion, by the first introduced atom.In similar conditions toluidines 4a and 5a yield bromoderivatives 4b (80percent) and 5b (47percent), respectively.
Berrier C.,Jacquesy, J. C.,Renoux, A.
p. 93 - 97
(2007/10/02)