27715-44-2Relevant articles and documents
Chains, layers, channels, and more: Supramolecular chemistry of potent diphosphonic tectons with tuned flexibility. the generation of pseudopolymorphs, polymorphs, and adducts
Bialek, Michal J.,Zareba, Jan K.,Janczak, Jan,Zon, Jerzy
, p. 4039 - 4050 (2013)
Naphthalene-1,5-diphosphonic acid [C10H6(PO 3H2)2, H4NDP(1,5), 1] and its more flexible counterpart, naphthalene-1,5-bis(methylphosphonic) acid [C 10H6(CH2PO3H2) 2, H4NDP(1C,5C), 2], have been synthesized, characterized, and used as building blocks in supramolecular assemblies with 4-(N,N-dimethylamino)pyridine (DMAP) and morpholine. The two acids generate two distinct solvatomorphs each, with and without dimethyl sulfoxide (DMSO) molecules. The two adducts of H4NDP(1,5) with DMAP (3A and 3B) reveal conformational polymorphism caused by the rotation of phosphonic groups. The two adducts of H4NDP(1C,5C) show unexpected structural diversity, generating a symmetric hydrogen bond and creating a layered structure, 4A, or a channel structure, 4B. The adducts of both acids with morpholine (5A and 5B) allow for observing the influence of the conformational flexibility of the acids on the dimensionality of a final hydrogen bond network, which is in general higher for H4NDP(1C,5C). The structural motifs and trends are analyzed in terms of the geometric criteria of these interactions. For the first time, Hirshfeld surface analysis has also been applied for the investigation of supramolecular interactions of phosphonic acids in different protonation states.
Desulfonylative Iodination of Naphthalenesulfonyl Chlorides with Zinc Iodide or Potassium Iodide Catalyzed by Dichlorobis(benzonitrile)palladium(II) in the Presence of Lithium Chloride and Titanium(IV) Isopropoxide
Satoh, Tetsuya,Itoh, Kenji,Miura, Masahiro,Nomura, Masakatsu
, p. 2121 - 2123 (1993)
Iodination of naphthalenesulfonyl chlorides accompanied by desulfonylation efficiently proceeded on treatment with either zinc iodide or potassium iodide using a catalyst system of /LiCl/Ti(OPr2)4.
Net-Clipping: An Approach to Deduce the Topology of Metal-Organic Frameworks Built with Zigzag Ligands
Ghasempour, Hosein,Guillerm, Vincent,Imaz, Inhar,Juanhuix, Judith,Maspoch, Daniel,Morsali, Ali,Ortín-Rubio, Borja
, p. 9135 - 9140 (2020)
Herein we propose a new approach for deducing the topology of metal-organic frameworks (MOFs) assembled from organic ligands of low symmetry, which we call net-clipping. It is based on the construction of nets by rational deconstruction of edge-transitive
Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates
Klein, Philippe,Lechner, Vivien Denise,Schimmel, Tanja,Hintermann, Lukas
supporting information, p. 176 - 180 (2019/12/11)
The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C?X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C?O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C?X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4-diazadiene catalyst system, in which 1,4-diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross-coupling or electrophilic substitution reactions.
Modular Approach to the Synthesis of Two-Dimensional Angular Fused Acenes
Feofanov, Mikhail,Akhmetov, Vladimir,Sharapa, Dmitry I.,Amsharov, Konstantin
supporting information, p. 1698 - 1702 (2020/01/31)
Herein, we present a modular approach to pristine angularly fused planar acenes. The approach includes the Pd-catalyzed fusion of several building blocks and implements a dehydrative ?-extension (DPEX) reaction as a key step enabling facile access to diverse two-dimensional acenes. The scope was demonstrated on nine examples with up to quantitative yield.
Bioavailability Studies and in vitro Profiling of the Selective Excitatory Amino Acid Transporter Subtype 1 (EAAT1) Inhibitor UCPH-102
Haym, Isabell,Huynh, Tri H. V.,Hansen, Stinne W.,Pedersen, Martin H. F.,Ruiz, Josep A.,Erichsen, Mette N.,Gynther, Mikko,Bj?rn-Yoshimoto, Walden E.,Abrahamsen, Bjarke,Bastlund, Jesper F.,Bundgaard, Christoffer,Eriksen, Anette L.,Jensen, Anders A.,Bunch, Lennart
, p. 403 - 419 (2016/03/01)
Although the selective excitatory amino acid transporter subtype 1 (EAAT1) inhibitor UCPH-101 has become a standard pharmacological tool compound for in vitro and ex vivo studies in the EAAT research field, its inability to penetrate the blood-brain barrier makes it unsuitable for in vivo studies. In the present study, per os (p.o.) administration (40 mg kg-1) of the closely related analogue UCPH-102 in rats yielded respective plasma and brain concentrations of 10.5 and 6.67 μm after 1 h. Three analogue series were designed and synthesized to improve the bioavailability profile of UCPH-102, but none displayed substantially improved properties in this respect. In vitro profiling of UCPH-102 (10 μm) at 51 central nervous system targets in radioligand binding assays strongly suggests that the compound is completely selective for EAAT1. Finally, in a rodent locomotor model, p.o. administration of UCPH-102 (20 mg kg-1) did not induce acute effects or any visible changes in behavior. EAAT1 inhibition beyond the BBB: In the present study, oral administration (40 mg kg-1) of the selective excitatory amino acid transporter subtype 1 (EAAT1) inhibitor UCPH-102 in rats yielded respective plasma and brain concentrations of 10.5 and 6.67 μm after 1 h. In vitro profiling of UCPH-102 (10 μm) at 51 central nervous system targets in radioligand binding assays strongly suggests that the compound is fully selective for EAAT1.
Self-assembled supramolecular clusters based on phosphines and coinage metals: Tetrahedra, helicates, and mesocates
Lim, Sang Ho,Cohen, Seth M.
, p. 7862 - 7872 (2013/08/23)
An array of coordination-driven supramolecular metal-ligand clusters has been synthesized using polytopic phosphine ligands and coinage metals (Cu +, Ag+, Au+). Rigid 3-fold or 2-fold symmetric phosphine ligands have been prepared: 1,3,5-tris((4-(diphenylphosphino)ethynyl) phenyl)benzene) (tppepb, L1), 1,4-bis((diphenylphosphino)ethynyl) benzene (1,4-dppeb, L2), 1,3-bis((diphenylphosphino)ethynyl)benzene (1,3-dppeb, L3), 2,6-bis((diphenylphosphino)ethynyl)pyridine (2,6-dppep, L4), and 1,5-bis((diphenylphosphino)ethynyl)naphthalene (1,5-dppen, L5). Self-assembly of these ligands with coinage metals produces four different types of metal-ligand clusters, or in some cases coordination polymers, depending on number and relative geometry of the phosphine donor atoms. Supramolecular tetrahedral clusters of the formula M 4(L1)4I4 (M = Cu+, Ag+, Au+) were obtained with the tppepb ligand, encapsulating solvent molecules (either CH2Cl2 or DMF) as guests within the central cavity of the clusters. The ligands 1,3-dppeb (L 3) and 2,6-dppep (L4) give achiral, triple-stranded, dinuclear mesocates with the formula M2(L)3I2 (M = Cu+ or Au+). In contrast, the ligand 1,4-dppeb (L2) generates a triple-stranded, dinuclear helicate with Cu +, but a coordination polymer with Au+ (both with the empirical formula M2(L2)3I2). Finally, coordination polymers were obtained from 1,5-dppen (L5) with Cu+. The clusters have been fully characterized by single crystal X-ray crystallography, high-resolution mass spectrometry, 1H NMR, and 31P NMR.
Isomeric carbazolocarbazoles: Synthesis, characterization and comparative study in Organic Field Effect Transistors
Mas-Montoya, Miriam,Ortiz, Rocio Ponce,Curiel, David,Espinosa, Arturo,Allain, Magali,Facchetti, Antonio,Marks, Tobin J.
, p. 1959 - 1969 (2013/05/21)
We report here the synthesis and characterization of a new family of isomeric carbazolocarbazole derivatives, namely carbazolo[1,2-a]carbazole, carbazolo[3,2-b]carbazole and carbazolo[4,3-c]carbazole. Thermal, optical, electrochemical, morphological and semiconducting properties have been studied to understand the influence of geometrical isomerism on the optoelectronic properties of these compounds. Different packing patterns have been observed by single crystal X-ray diffraction (XRD) which then correlate with the different morphologies of the evaporated thin films studied by XRD and Atomic Force Microscopy (AFM). The effect of N-substituents has also been evaluated for one of the isomers revealing a noticeable influence on the performance as organic semiconductors in Organic Field Effect Transistors (OFETs). A good p-channel field effect has been determined for N,N′-dioctylcarbazolo[4,3-c]carbazole with a mobility of 0.02 cm2 V-1 s-1 and I on/Ioff ratio of 106 in air. These preliminary results demonstrate the promising properties of molecular carbazolocarbazole systems which should be further explored in the area of organic semiconducting materials.
A facile approach to highly efficient and thermally stable solid-state emitters: Knitting up AIE-active TPE luminogens by aryl linkers
Chan, Carrie Yin Kwan,Lam, Jacky Wing Yip,Zhao, Zujin,Deng, Chunmei,Chen, Shuming,Lu, Ping,Sung, Herman H.Y.,Kwok, Hoi Sing,Ma, Yuguang,Williams, Ian D.,Tang, Ben Zhong
, p. 949 - 958 (2013/01/15)
A facile approach to thermally stable and efficient solid-state emitters is proposed. By hooking up tetraphenylethene (TPE) units through aryl linkers under Suzuki coupling conditions, a series of arylene bis(tetraphenylethene)s (TPE-Ar-TPE Ar = 2, 5-dime
A facile approach to highly efficient and thermally stable solid-state emitters: Knitting up aie-active tpe luminogens by aryl linkers
Chan, Carrie Yin Kwan,Lam, Jacky Wing Yip,Zhao, Zujin,Deng, Chunmei,Chen, Shuming,Lu, Ping,Sung, Herman H. Y.,Kwok, Hoi Sing,Ma, Yuguang,Williams, Ian D.,Tang, Ben Zhong
, p. 949 - 958 (2014/01/17)
A facile approach to thermally stable and efficient solid-state emitters is proposed. By hooking up tetraphenylethene (TPE) units through aryl linkers under Suzuki coupling conditions, a series of arylene bis(tetraphenylethene)s (TPE-Ar-TPE Ar=2,5- dimeth
