316,603 Works

Simple isophthalamides/dipicolineamides as active transmembrane anion transporters

Giacomo Picci, Israel Carreira-Barral, Daniel Alonso-Carrillo, David Sanz-González, Pablo Fernández-López, María García-Valverde, Claudia Caltagirone & Roberto Quesada
Eight N,N´-diarylisophthalamide/dipicolineamide derivatives have been synthesised and fully characterised, both in solution and in the solid state. The transmembrane anion transport properties of these compounds have been studied by chloride-selective electrode and fluorescence experiments. The substitution pattern of the aromatic moieties determines the transport properties of these systems, with those containing electron-withdrawing groups in their structures being the most active ones of the series.

Mechanosensitive membrane probes: push-pull papillons

Heorhii V. Humeniuk, Giuseppe Licari, Eric Vauthey, Naomi Sakai & Stefan Matile
Design, synthesis and evaluation of push-pull N,N′-diphenyl-dihydrodibenzo[a,c]phenazines are reported. Consistent with theoretical predictions, donors and acceptors attached to the bent mechanophore are shown to shift absorption maxima to either red or blue, depending on their positioning in the chromophore. Redshifted excitation of push-pull fluorophores is reflected in redshifted emission of both bent and planar excited states. The intensity ratios of the dual emission in more and less polar solvents imply that excited-state (ES) planarization decelerates...

Simple isophthalamides/dipicolineamides as active transmembrane anion transporters

Giacomo Picci, Israel Carreira-Barral, Daniel Alonso-Carrillo, David Sanz-González, Pablo Fernández-López, María García-Valverde, Claudia Caltagirone & Roberto Quesada
Eight N,N´-diarylisophthalamide/dipicolineamide derivatives have been synthesised and fully characterised, both in solution and in the solid state. The transmembrane anion transport properties of these compounds have been studied by chloride-selective electrode and fluorescence experiments. The substitution pattern of the aromatic moieties determines the transport properties of these systems, with those containing electron-withdrawing groups in their structures being the most active ones of the series.

Evaluating hydrogen-bond propensity, hydrogen-bond coordination and hydrogen-bond energy as tools for predicting the outcome of attempted co-crystallisations

Nandini Sarkar & Christer B. Aakeröy
Two different structure-informatics based methods and one approach based on hydrogen-bond interaction energies were evaluated for their abilities to predict the experimental outcomes of attempted co-crystallisations between two known drug molecules, Nevirapine and Diclofenac, and a series of potential co-formers. The hydrogen-bond propensity (HBP) tool gave the correct result in 26 out of 30 cases, whereas a hydrogen-bond coordination (HBC) method predicted the correct outcome in 22 out of 30 cases. Finally, calculated hydrogen-bond energies...

Mechanosensitive membrane probes: push-pull papillons

Heorhii V. Humeniuk, Giuseppe Licari, Eric Vauthey, Naomi Sakai & Stefan Matile
Design, synthesis and evaluation of push-pull N,N′-diphenyl-dihydrodibenzo[a,c]phenazines are reported. Consistent with theoretical predictions, donors and acceptors attached to the bent mechanophore are shown to shift absorption maxima to either red or blue, depending on their positioning in the chromophore. Redshifted excitation of push-pull fluorophores is reflected in redshifted emission of both bent and planar excited states. The intensity ratios of the dual emission in more and less polar solvents imply that excited-state (ES) planarization decelerates...

Evaluating hydrogen-bond propensity, hydrogen-bond coordination and hydrogen-bond energy as tools for predicting the outcome of attempted co-crystallisations

Nandini Sarkar & Christer B. Aakeröy
Two different structure-informatics based methods and one approach based on hydrogen-bond interaction energies were evaluated for their abilities to predict the experimental outcomes of attempted co-crystallisations between two known drug molecules, Nevirapine and Diclofenac, and a series of potential co-formers. The hydrogen-bond propensity (HBP) tool gave the correct result in 26 out of 30 cases, whereas a hydrogen-bond coordination (HBC) method predicted the correct outcome in 22 out of 30 cases. Finally, calculated hydrogen-bond energies...

Synthesis and spectroscopic studies of diaza-8-crown-4-dinitrophenyl ethers

Claudia Galea, Damjan Makuc, Konrad Szaciłowski, Janez Plavec & David C. Magri
The macrocycles 3,7-bis(3-nitrophenyl)-1,5,3,7-dioxadiazocane 1 and 3,7-bis(4-nitrophenyl)-1,5,3,7-dioxadiazocane 2 were synthesised by a one-pot reaction with substituted nitroanilines and formaldehyde under acidic conditions. The same reaction with 2-nitroaniline yielded N, N’-(oxybis(methylene))bis(2-nitroaniline) 3 rather than 3,7-bis(2-nitrophenyl)-1,5,3,7-dioxadiazocane 4. The yellow powders 1–3 were characterised by 1H/13C/15N NMR, FTIR and HRMS. The photophysical properties were studied by UV-visible absorption and steady-state fluorescence spectroscopy. Acid dissociation constants were determined by UV-visible absorption titrations in 1:1 (v/v) acetonitrile/water to be 0.80 and...

IrIII as a strategy for preorganisation in H-bonded motifs

Barbora Balónová, Helena J Shepherd, Christopher J Serpell & Barry A Blight
We report how four sets of thiourea-based heterodimers interact, and how incorporation of a metal centre imparts reduced degrees of rotational freedom. Through single-crystal X-ray diffraction, 1H NMR, and UV-vis analysis, the interactions of these systems are dissected and presented. These motifs are considered to be stable and desirable for supramolecular hydrogen-bonded functional materials. Interpretation of the structural design of thiourea-based ligand and its incorporation into metal complexes can contribute to the understanding of preorganised...

IrIII as a strategy for preorganisation in H-bonded motifs

Barbora Balónová, Helena J Shepherd, Christopher J Serpell & Barry A Blight
We report how four sets of thiourea-based heterodimers interact, and how incorporation of a metal centre imparts reduced degrees of rotational freedom. Through single-crystal X-ray diffraction, 1H NMR, and UV-vis analysis, the interactions of these systems are dissected and presented. These motifs are considered to be stable and desirable for supramolecular hydrogen-bonded functional materials. Interpretation of the structural design of thiourea-based ligand and its incorporation into metal complexes can contribute to the understanding of preorganised...

Synthesis and spectroscopic studies of diaza-8-crown-4-dinitrophenyl ethers

Claudia Galea, Damjan Makuc, Konrad Szaciłowski, Janez Plavec & David C. Magri
The macrocycles 3,7-bis(3-nitrophenyl)-1,5,3,7-dioxadiazocane 1 and 3,7-bis(4-nitrophenyl)-1,5,3,7-dioxadiazocane 2 were synthesised by a one-pot reaction with substituted nitroanilines and formaldehyde under acidic conditions. The same reaction with 2-nitroaniline yielded N, N’-(oxybis(methylene))bis(2-nitroaniline) 3 rather than 3,7-bis(2-nitrophenyl)-1,5,3,7-dioxadiazocane 4. The yellow powders 1–3 were characterised by 1H/13C/15N NMR, FTIR and HRMS. The photophysical properties were studied by UV-visible absorption and steady-state fluorescence spectroscopy. Acid dissociation constants were determined by UV-visible absorption titrations in 1:1 (v/v) acetonitrile/water to be 0.80 and...

A highly fluorescent PN-heterocycle-fused pyrene derivative with strong self-dimerisation through hydrogen bonding

Jeremy P. Bard, Jenna L. Mancuso, Chun-Lin Deng, Lev N. Zakharov, Darren W. Johnson & Michael M. Haley
The pyrene moiety has been utilised in a variety of systems that exhibit either ‘turn on’ or ‘turn off’ fluorescence in response to specific analytes. Continued development of hydrogen bonding pyrene-containing scaffolds seeks to establish a wider substrate scope and utility of these hosts. Herein, we report one such example in the form of a pyrene-containing phosphaquinolinone. This molecule exhibits both strong dimerisation in the solution state and π–π stacking within the pyrene backbone in...

Aromatic interactions of allenyl-anthracene derivatives with pi-electron acceptor molecules: an experimental and computational study

Ángel Vidal-Vidal, José-Lorenzo Alonso-Gómez, María Magdalena Cid & Marta Marín-Luna
Electrostatic effects play an important role in aromatic interactions towards molecular recognition. Anthraceno-allenophanes are cyclic π-conjugated aromatic systems able to recognise complementary molecules through aromatic interactions. A computational and experimental study has shown that the dispersive contribution is the predominant stabilising term in the interaction of an allenyl-anthracene derivative with relevant π-acceptor molecules, such as pentafluorophenol, picric acid and 2,3-dichloro-5,6-dicyano-1,4-quinone.

Aromatic interactions of allenyl-anthracene derivatives with pi-electron acceptor molecules: an experimental and computational study

Ángel Vidal-Vidal, José-Lorenzo Alonso-Gómez, María Magdalena Cid & Marta Marín-Luna
Electrostatic effects play an important role in aromatic interactions towards molecular recognition. Anthraceno-allenophanes are cyclic π-conjugated aromatic systems able to recognise complementary molecules through aromatic interactions. A computational and experimental study has shown that the dispersive contribution is the predominant stabilising term in the interaction of an allenyl-anthracene derivative with relevant π-acceptor molecules, such as pentafluorophenol, picric acid and 2,3-dichloro-5,6-dicyano-1,4-quinone.

Selective recognition of small hydrogen bond acceptors by a calix[6]arene-based molecular container

Roy Lavendomme, Florent Desroches, Steven Moerkerke, Filip Topić, Johan Wouters, Kari Rissanen, Michel Luhmer & Ivan Jabin
Selective molecular recognition is of primary importance for applications such as sensing and separation of chemicals. This work describes the host-guest and crystallisation properties of a penta-carbamated calix[6]arene designed as a molecular container with a H-donating recognition group directed towards the heart of the cavity. As demonstrated by NMR spectroscopy and X-ray diffraction studies, this macrocyclic receptor can selectively recognise small H-bond acceptors through one or two hydrogen bonds, the guests nesting inside the polyaromatic...

A highly fluorescent PN-heterocycle-fused pyrene derivative with strong self-dimerisation through hydrogen bonding

Jeremy P. Bard, Jenna L. Mancuso, Chun-Lin Deng, Lev N. Zakharov, Darren W. Johnson & Michael M. Haley
The pyrene moiety has been utilised in a variety of systems that exhibit either ‘turn on’ or ‘turn off’ fluorescence in response to specific analytes. Continued development of hydrogen bonding pyrene-containing scaffolds seeks to establish a wider substrate scope and utility of these hosts. Herein, we report one such example in the form of a pyrene-containing phosphaquinolinone. This molecule exhibits both strong dimerisation in the solution state and π–π stacking within the pyrene backbone in...

Selective recognition of small hydrogen bond acceptors by a calix[6]arene-based molecular container

Roy Lavendomme, Florent Desroches, Steven Moerkerke, Filip Topić, Johan Wouters, Kari Rissanen, Michel Luhmer & Ivan Jabin
Selective molecular recognition is of primary importance for applications such as sensing and separation of chemicals. This work describes the host-guest and crystallisation properties of a penta-carbamated calix[6]arene designed as a molecular container with a H-donating recognition group directed towards the heart of the cavity. As demonstrated by NMR spectroscopy and X-ray diffraction studies, this macrocyclic receptor can selectively recognise small H-bond acceptors through one or two hydrogen bonds, the guests nesting inside the polyaromatic...

Distinguishing amines with an amino acid appended resorcinarene-based cavitand

Tayyebeh Panahi, Holly L. Anderson, Karla I. Castro, John D. Lamb & Roger G. Harrison
Resorcinarene-based deep cavitands including glutamic acid methyl resorcinarene (GMA) and glutamic acid undecyl resorcinarene (GUA) have been synthesised and their amine binding properties analysed. The cavitands are designed with hydrogen bonding groups on their upper rim (glutamic acids) and hydrophobic groups, on their lower rims. Along with the aromatic groups of the resorcinarene, these cavitands have many sites for guest binding. The cavitands form kite-like structures in dimethylsulfoxide, acetone, and water. The binding of GMA...

Distinguishing amines with an amino acid appended resorcinarene-based cavitand

Tayyebeh Panahi, Holly L. Anderson, Karla I. Castro, John D. Lamb & Roger G. Harrison
Resorcinarene-based deep cavitands including glutamic acid methyl resorcinarene (GMA) and glutamic acid undecyl resorcinarene (GUA) have been synthesised and their amine binding properties analysed. The cavitands are designed with hydrogen bonding groups on their upper rim (glutamic acids) and hydrophobic groups, on their lower rims. Along with the aromatic groups of the resorcinarene, these cavitands have many sites for guest binding. The cavitands form kite-like structures in dimethylsulfoxide, acetone, and water. The binding of GMA...

Oxidant-responsive ferrocene-based cyclodextrin complex coacervate core micelles

Camilla Facciotti, Vittorio Saggiomo, Simon Van Hurne, Anton Bunschoten, Rebecca Kaup & Aldrik H. Velders
Coacervate-core micelles are considered promising materials for several applications, from catalysis to drug delivery. However, oxidant-responsive coacervate-core micelles, able to undergo structural changes upon specific oxidation stimuli, are not well reported. Here, we present a novel ferrocene–dipicolinic acid derivative as redox-responsive subcomponent to be incorporated in cyclodextrin-based coacervate core micelles, C4Ms, with tuneable core structure and responsiveness towards H2O2 treatment. The Fc-C4Ms are formed combining three orthogonal supramolecular interactions, namely (i) metal-to-ligand coordination between europium(III)...

Oxidant-responsive ferrocene-based cyclodextrin complex coacervate core micelles

Camilla Facciotti, Vittorio Saggiomo, Simon Van Hurne, Anton Bunschoten, Rebecca Kaup & Aldrik H. Velders
Coacervate-core micelles are considered promising materials for several applications, from catalysis to drug delivery. However, oxidant-responsive coacervate-core micelles, able to undergo structural changes upon specific oxidation stimuli, are not well reported. Here, we present a novel ferrocene–dipicolinic acid derivative as redox-responsive subcomponent to be incorporated in cyclodextrin-based coacervate core micelles, C4Ms, with tuneable core structure and responsiveness towards H2O2 treatment. The Fc-C4Ms are formed combining three orthogonal supramolecular interactions, namely (i) metal-to-ligand coordination between europium(III)...

MOESM2 of The performance of the EMS triage (RETTS-p) and the agreement between the field assessment and final hospital diagnosis: a prospective observational study among children

Carl Magnusson, Johan Herlitz, Thomas Karlsson, Maria Jiménez-Herrera & Christer Axelsson
Additional file 2. Paediatric life-threatening conditions: a list of conditions considered to be time-sensitive.

Additional file 2 of The performance of the EMS triage (RETTS-p) and the agreement between the field assessment and final hospital diagnosis: a prospective observational study among children

Carl Magnusson, Johan Herlitz, Thomas Karlsson, Maria Jiménez-Herrera & Christer Axelsson
Additional file 2. Paediatric life-threatening conditions: a list of conditions considered to be time-sensitive.

MOESM1 of The performance of the EMS triage (RETTS-p) and the agreement between the field assessment and final hospital diagnosis: a prospective observational study among children

Carl Magnusson, Johan Herlitz, Thomas Karlsson, Maria Jiménez-Herrera & Christer Axelsson
Additional file 1. The paediatric risk of mortality III – acute physiology score (PRISM III-APS): Life-threatening vital signs for paediatrics according to the PRISM III-APS.

Additional file 1 of The performance of the EMS triage (RETTS-p) and the agreement between the field assessment and final hospital diagnosis: a prospective observational study among children

Carl Magnusson, Johan Herlitz, Thomas Karlsson, Maria Jiménez-Herrera & Christer Axelsson
Additional file 1. The paediatric risk of mortality III – acute physiology score (PRISM III-APS): Life-threatening vital signs for paediatrics according to the PRISM III-APS.

Additional file 1 of MetaCon: unsupervised clustering of metagenomic contigs with probabilistic k-mers statistics and coverage

Jia Qian & Matteo Comin
Supplementary Material. (PDF 205 kb)

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