189078-60-2Relevant academic research and scientific papers
Zwitterionic guanidinium compounds serve as electroneutral anion hosts
Berger, Michael,Schmidtchen, Franz P.
, p. 9986 - 9993 (1999)
The complexation of anions in solvating phases by artificial receptors requires the total or at least partial replacement of their solvation shells by the mutual supramolecular interactions. Supplementing wellknown approaches that rely on net electrostatic charges or extensive hydrogen bonding for guest complexation the present work focuses on the alternative concept of charge separation in the host to create a cationic site suitable for strong interaction with negatively charged guests. An anionic moiety balancing the overall host charge to zero is incorporated in a way to prevent collapsing into an ion pair. Using bicyclic guanidinium anchor groups for direct guest binding and a closo-borane cluster as an anionic countercharge the ditopic zwitterionic host 17 was designed and prepared in a convergent synthetic scheme. Despite its electroneutrality 17 binds inorganic and organic oxoanions such as sulfate, oxalate, squarate and p-nitrophenyl phosphate with affinity constants reaching 3.1 x 104 M-1 in DMSO (squarate2-) or 1.1 x 105 M-1 in acetonitrile (p-nitrophenyl phosphate2-). Clean 1:1 host-guest stoichiometry is found in dilute solutions, whereas at higher concentrations different complex compositions and host dimerization are observed. Titration calorimetry reveals the major role of entropy in host-guest association. In essence, anion binding by 17 and its congeners in strongly solvating solvents such as DMSO is favored by massive positive association entropies that in the case of sulfate complexation to 17 override an unfavorable positive binding enthalpy constituting an exclusively entropy-driven process.
Rotaxanes from tetralactams
Gibson, Harry W.,Wang, Hong,Niu, Zhenbin,Slebodnick, Carla,Zhakharov, Lev N.,Rheingold, Arnold L.
, p. 1270 - 1280 (2012/06/18)
Attempts to incorporate a tetralactam (3a) into a side-chain polyrotaxane by formation of its complex with p-tritylphenolate and reaction with poly(vinybenzyl chloride) failed, probably due to steric hindrance. However, three new small molecule model rota
Jacketed homopolymer with bipolar dendritic side groups and its applications in electroluminescent devices
Zhang, Wei,Jin, Hao,Wang, Dan,Chu, Zengze,Shen, Zhihao,Zou, Dechun,Fan, Xinghe
experimental part, p. 581 - 589 (2012/04/23)
A dendritic monomer with bipolar side groups containing dendritic carbazole and oxadiazole structures was synthesized by a convergent strategy. The homopolymer was synthesized through a conventional radical polymerization. The number-average molecular wei
OPTICAL-ISOMER SEPARATING AGENT FOR CHROMATOGRAPHY AND PROCESS FOR PRODUCING THE SAME
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Page/Page column 10-11, (2010/12/18)
A novel optical-isomer separating agent for chromatography is provided which has, as a chiral selector, a macrocyclic amide compound having the ability to function as a chiral shift agent. The optical-isomer separating agent for chromatography is formed by bonding, with a carrier by chemical bonding, a specific ring structure containing an asymmetry recognition site, an amide group as a hydrogen-bond donor site, and a hydrogen-bond acceptor site.
Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity
Ema, Tadashi,Tanida, Daisuke,Sugita, Kyoko,Sakai, Takashi,Miyazawa, Ken-Ichiro,Ohnishi, Atsushi
supporting information; experimental part, p. 2365 - 2368 (2009/05/27)
(Chemical Equation Presented) Chiral macrocycles with the hydrogen bond donor/acceptor sites in the cavity were synthesized and covalently bonded to silica gel to give chiral stationary phases (CSPs), which showed excellent abilities to resolve various chiral compounds, such as benzoin and Co(acac) 3, in HPLC. Various organic solvents could be used as the mobile phase to optimize the resolution efficiency of CSPs, and in some cases, even MeCN, MeOH, and CO2 could be used for the complete resolution of enantiomers.
Self-organization of dendritic supermolecules, based on isocyanide-gold(I), -copper(I), -palladium(II), and -platinum(II) complexes, into micellar cubic mesophases
Coco, Silverio,Cordovilla, Carlos,Donnio, Bertrand,Espinet, Pablo,Garcia-Casas, Maria Jesus,Guillon, Daniel
experimental part, p. 3544 - 3552 (2009/05/07)
First- and second-generation dendrimers with an isocyanide group as the focal functional point (CN-Gn; n: 1,2) and their corresponding organometallic complexes [MCl(CN-Gn)] (M: Au, Cu), [{CuCl(CN-G n)2}2/s
Molecular factors responsible for the formation of the axially polar columnar mesophase ColhPA
Matraszek, Joanna,Mieczkowski, Jozef,Pociecha, Damian,Gorecka, Ewa,Donnio, Bertrand,Guillon, Daniel
, p. 3377 - 3385 (2008/01/06)
The structure of hexacatenar bent-shape molecules has been systematically modified in order to determine the main molecular factors responsible for the appearance of the axially polar columnar mesophase. It was found that the stability of the polar phase
Ion channels from linear and branched bola-amphiphiles
Eggers,Fyles,Mitchell,Sutherland
, p. 1050 - 1058 (2007/10/03)
The synthesis and characterization of the ion channel activity of three new bola-amphiphiles is described. These compounds are conceptually derived from a previously reported bis-cyclophane bola-amphiphile through opening of the cyclophanes to acyclic str
