Karel J. Hartlieb

ORCID: 0000-0003-0160-0561
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Research Areas
  • Crystallization and Solubility Studies
  • X-ray Diffraction in Crystallography
  • Supramolecular Chemistry and Complexes
  • Porphyrin and Phthalocyanine Chemistry
  • Molecular Sensors and Ion Detection
  • Luminescence and Fluorescent Materials
  • Molecular Junctions and Nanostructures
  • Metal-Organic Frameworks: Synthesis and Applications
  • Synthesis and Properties of Aromatic Compounds
  • Crystallography and molecular interactions
  • Gold and Silver Nanoparticles Synthesis and Applications
  • Click Chemistry and Applications
  • Nanomaterials for catalytic reactions
  • Supramolecular Self-Assembly in Materials
  • Magnetism in coordination complexes
  • Organic and Molecular Conductors Research
  • Advanced NMR Techniques and Applications
  • Nanoparticle-Based Drug Delivery
  • Nanoplatforms for cancer theranostics
  • Photochemistry and Electron Transfer Studies
  • Sulfur Compounds in Biology
  • Membrane Separation and Gas Transport
  • Pickering emulsions and particle stabilization
  • Conducting polymers and applications
  • Nanocluster Synthesis and Applications

Northwestern University
2012-2018

Northwest University
2013

The University of Western Australia
2007-2012

Clarkson University
2010

Porous metal–organic frameworks (MOFs) have been studied in the context of a wide variety applications, particularly relation to molecular storage and separation sciences. Recently, we reported green, renewable framework material composed γ-cyclodextrin (γ-CD) alkali metal salts—namely, CD-MOF. This porous has shown facilitate mixtures alkylaromatic compounds, including BTEX mixture (benzene, toluene, ethylbenzene, regioisomers xylene), into their pure components, both liquid gas phases, an...

10.1021/jacs.5b12860 article EN publisher-specific-oa Journal of the American Chemical Society 2016-01-27

Although ibuprofen is one of the most widely used nonsteroidal anti-inflammatory drugs (NSAIDs), it exhibits poor solubility in aqueous and physiological environments as a free acid. In order to improve its oral bioavailability rate uptake, extensive research into development new formulations has been undertaken, including use excipients well salts, such lysinate ibuprofen, sodium salt. The ultimate goals these studies are reduce time required for maximum uptake this period directly...

10.1021/acs.molpharmaceut.7b00168 article EN publisher-specific-oa Molecular Pharmaceutics 2017-03-29

Most organic radicals possess short lifetimes and quickly undergo dimerization or oxidation. Here, we report on the synthesis by radical templation of a class air- water-stable radicals, trapped within homo[2]catenane composed two rigid fixed cyclobis(paraquat-p-phenylene) rings. The highly energetic octacationic homo[2]catenane, which is capable accepting up to eight electrons, can be configured reversibly, both chemically electrochemically, between each one six experimentally accessible...

10.1126/science.1228429 article EN Science 2013-01-24

We report the one-pot synthesis and electrochemical switching mechanism of a family electrochemically bistable 'daisy chain' rotaxane switches based on derivative so-called 'blue box' (BB(4+)) tetracationic cyclophane cyclobis(paraquat-p-phenylene). These mechanically interlocked molecules are prepared by stoppering kinetically solution-state assemblies self-complementary monomer comprising BB(4+) ring appended with viologen (V(2+)) 1,5-dioxynaphthalene (DNP) recognition units using click...

10.1021/ja500675y article EN Journal of the American Chemical Society 2014-02-10

Metal–organic frameworks (MOFs) are known to facilitate energy-efficient separations of important industrial chemical feedstocks. Here, we report how a class green MOFs—namely CD-MOFs—exhibits high shape selectivity toward aromatic hydrocarbons. CD-MOFs, which consist an extended porous network γ-cyclodextrins (γ-CDs) and alkali metal cations, can separate wide range benzenoid compounds as result their relative orientation packing within the transverse channels formed from linking (γ-CD)6...

10.1021/ja511878b article EN Journal of the American Chemical Society 2015-03-25

After the manner in which coenzymes often participate binding of substrates active sites enzymes, pillar[5]arene, a macrocycle containing five hydroquinone rings linked through their para positions by methylene bridges, modifies properties cucurbit[6]uril, such that latter templates azide–alkyne cycloadditions do not occur presence only composed six glycoluril residues doubly nitrogen atoms to each other groups. Here, we describe how combination pillar[5]arene and cucurbit[6]uril interacts...

10.1021/ja407229h article EN Journal of the American Chemical Society 2013-09-23

A fullerene-based photosensitizer is incorporated postsynthetically into a Zr6 -based MOF, NU-1000, for enhanced singlet oxygen production. The structural organic linkers in the MOF platform also act as photosensitizers which contribute to overall generation of from material under UV irradiation. generated by MOF/fullerene shown oxidize sulfur mustard selectively less toxic bis(2-chloroethyl)sulfoxide with half-life only 11 min.

10.1002/chem.201604972 article EN Chemistry - A European Journal 2016-10-25

The effect of para-substituents on the crystal packing phenols has been investigated, for systems bearing nonpolar groups (tert-butyl and benzyl, compounds 1 2, respectively) methylene linked bis-phenol polar nitro (compound 3). Remarkable asymmetric unit six molecules, which form infinite helical hydrogen bonded arrays in extended structures, whereas compound 3 coplanar with phenol rings forms almost columnar arrays. Hirshfeld surface analysis is used to show that despite a nearly identical...

10.1021/cg1011605 article EN Crystal Growth & Design 2010-11-08

The 2,9-dimethyldiazaperopyrenium dication can be made from a ubiquitous and inexpensive feedstock in three simple steps as its chloride salt. When mixed with powdered graphite at 23 °C, this behemoth of molecular compound exfoliates to graphene water under mild conditions.

10.1002/adma.201205157 article EN Advanced Materials 2013-04-03

A tristable [2]catenane, composed of a macrocyclic polyether incorporating 1,5-dioxynaphthalene (DNP) and tetrathiafulvalene (TTF) units along with 4,4'-bipyridinium (BIPY(•+)) radical cation as three very different potential recognition sites, interlocked mechanically the tetracationic cyclophane, cyclobis(paraquat-p-phenylene) (CBPQT(4+)), was synthesized by donor-acceptor templation, employing "threading-followed-by-cyclization" approach. In this catenane, movement CBPQT(4+) ring in its...

10.1021/jacs.5b09274 article EN publisher-specific-oa Journal of the American Chemical Society 2015-10-06

We report the template-directed synthesis of BlueCage(6+), a macrobicyclic cyclophane composed six pyridinium rings fused with two central triazines and bridged by three paraxylylene units. These moieties endow cage remarkably electron-poor cavity, which makes it powerful receptor for polycyclic aromatic hydrocarbons (PAHs). Upon forming 1:1 complex pyrene in acetonitrile, however, BlueCage⋅6 PF6 exhibits lower association constant Ka than its progenitor ExCage⋅6 PF6. A close inspection...

10.1002/anie.201408400 article EN Angewandte Chemie International Edition 2014-11-19

Abstract We announce the establishment of a new family macrocycles—the asararenes, which are based on para ‐methylene linked “asarol methyl ether” (1,2,4,5‐tetramethoxybenzene) units. Macrocycles with 6–12 aromatic units have been synthesized and isolated in single step from asarol ether paraformaldehyde. Even larger rings, up to 15 units, observed by high‐resolution mass spectrometry. Single‐crystal X‐ray structures asar[6]‐, asar[7]‐, asar[8]‐, asar[9]‐, asar[10]‐ asar[11]arene highlight...

10.1002/chem.201204097 article EN Chemistry - A European Journal 2013-02-18

CD-MOF, an extended framework incorporating the C8 symmetric cyclic oligosaccharide, γ-cyclodextrin (γ-CD), is based on coordination of alkali metal cations to alternating α-1,4-linked d-glucopyranosyl units primary and secondary faces γ-CD tori. Here, we report synthesis characterisation amino-functionalised CD-MOF that isostructural with pristine adsorbs CO2 permanently.

10.1039/c7cc03345a article EN Chemical Communications 2017-01-01

A porphyrin functionalised with pillar[5]arene and a viologen at its 5- 15-meso positions assembles in head-to-tail manner, producing linear supramolecular daisy chains dichloromethane. At high concentrations, it forms an organogel which has been investigated by electron microscopy rheological measurements, paving the way for preparation of other functional assemblies harness viologen⊂pillararene host-guest interactions.

10.1039/c5cc03717d article EN Chemical Communications 2015-01-01

The kinetics and thermodynamics of intramolecular electron transfer (IET) can be subjected to redox control in a bistable [2]rotaxane comprised dumbbell component containing an electron-rich 1,5-dioxynaphthalene (DNP) unit electron-poor phenylene-bridged bipyridinium (P-BIPY(2+)) cyclobis (paraquat-p-phenylene) (CBPQT(4+)) ring component. exists the ground-state co-conformation (GSCC) wherein CBPQT(4+) encircles DNP unit. Reduction leads CBPQT(2(•+)) diradical dication while P-BIPY(2+) is...

10.1073/pnas.1201561109 article EN Proceedings of the National Academy of Sciences 2012-06-08

The self-assembly and solid-state semiconducting properties of single crystals a trisradical tricationic complex composed the diradical dicationic cyclobis(paraquat-p-phenylene) (CBPQT2(•+)) ring methyl viologen radical cation (MV•+) are reported. An organic field effect transistor incorporating CBPQT2(•+)⊂MV•+ was constructed using lithographic techniques on silicon substrate shown to exhibit p-type semiconductivity with mobility 0.05 cm2 V–1 s–1. morphology characterized scanning electron...

10.1021/nn303553z article EN ACS Nano 2012-10-18

Molecules capable of performing highly efficient energy transfer and ultrafast photoinduced electron in well-defined multichromophoric structures are indispensable to the development artificial photofunctional systems. Herein, we report on synthesis, characterization, photophysical properties a rationally designed tetracationic cyclophane, DAPPBox4+, containing diazaperopyrenium (DAPP2+) unit an extended viologen (ExBIPY2+) unit, which linked together by two p-xylylene bridges. Both 1H NMR...

10.1021/jacs.6b13223 article EN publisher-specific-oa Journal of the American Chemical Society 2017-02-22

Zinc oxide nanoparticles are formed under continuous flow using spinning disc processing (SDP). Synthetic parameters such as temperature, rate, speed, and surface texture influence the reaction kinetics particle size in an ethanolic solution polyvinylpyrrolidone (PVP) a capping agent. SDP ensures intense mixing, accelerates nucleation growth, affords monodispersed ZnO with controlled size. UV−visible spectroscopy shows formation of particles down to 1.3 nm polydispersities approximately 10%,...

10.1021/cm0715646 article EN Chemistry of Materials 2007-10-23

A donor–acceptor [3]catenane incorporating two cyclobis(paraquat-p-phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses π-electron-deficient pocket. Contrary to expectation, negligible binding of hexaethylene glycol chain interrupted in its midriff π-electron-rich 1,5-dioxynaphthalene unit was observed acetonitrile. However, fortuitous solid-state superstructure the expected 1:1 complex revealed inability embrace any stabilizing [C–H···O] interactions between...

10.1021/ja3085115 article EN Journal of the American Chemical Society 2012-09-21

p-Phosphonic acid calix[5]arene forms molecular capsules in water based on two of the molecules, which can be loaded with carboplatin using intense shearing, and attached to single wall carbon nano-tubes. Spin coating onto a substrate affords 2 nm fibres stacked calixarenes, self-assembly understood modelling.

10.1039/c1cc11991e article EN Chemical Communications 2011-01-01

Two narrow-channel reactor designs have been developed and used in conjunction with gas–liquid segmented flow order to intensify reactions effect synthesis under continuous conditions, incorporating single pass recirculating capability, high pressure temperature. Silver nanoparticles approximately 3–5 nm diameter are accessible the average size depending on reaction temperature polyphosphate concentration, smaller more monodisperse produced at low concentrations temperatures. The use of...

10.1039/c000708k article EN Green Chemistry 2010-01-01

Three structures, based on γ-cyclodextrin (γ-CD) and metal ions (Cu2+, Li+, Na+, Rb+), have been prepared in aqueous alkaline media characterized structurally by single-crystal X-ray diffraction. Their dimeric assemblies adopt cylindrical channels along the c axes crystals. Coordinative hydrogen bonding between cylinders solvent molecules lead to formation of two-dimensional sheets, with identity alkali-metal ion strongly influencing precise nature solid-state structures. In case Rb+...

10.1021/ic301795j article EN Inorganic Chemistry 2013-02-22

This communication describes a mechanically interlocked molecule (MIM), capable of switchable and reversible linear molecular motion.

10.1039/c4ob01228c article EN cc-by-nc Organic & Biomolecular Chemistry 2014-01-01

Very small (∼2 nm) silver nanoparticles can be readily prepared using p-phosphonated calixarenes as templating agents and surfactants, at the same time allowing use of hydrogen gas an environmentally benign reductant.

10.1039/b823067f article EN Chemical Communications 2009-01-01

This paper describes the development and optimization of a nanoparticle delivery platform for anticancer agent, paclitaxel, using novel amphiphilic carrier, tetrahexyloxy-tetra-p-aminocalix[4]arene (A4C(6) ).Nanoparticles were successfully prepared at pH4 by an emulsion evaporation method whereby organic phase containing paclitaxel: A4C(6) (molar ratio 1:10) was dispersed probe sonication into aqueous 0.5% w/v polyvinyl alcohol as stabilizer.The drug-loaded nanoparticles had mean size...

10.1111/j.2042-7158.2012.01518.x article EN Journal of Pharmacy and Pharmacology 2012-04-23
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