Small molecule, large surface area: A rigid triptycene derivative self-assembles by hydrogen bonds to a porous crystal with one-dimensional channels of about 14 Å diameter. Solvents in the can be removed generate an extrinsic material specific BET area 2796 m2 g−1. Furthermore, gases selectively adsorbed within pores at 1 bar. Detailed facts importance specialist readers are published as "Supporting Information". Such documents peer-reviewed, but not copy-edited or typeset. They made...

One area of supramolecular chemistry involves the synthesis discrete three-dimensional molecules or aggregates through coordination metals. This field also concerns cage compounds constructed use such bonds. To date, there exists a broad variety compounds; however, analogous organic formed with only covalent bonds are relatively rare. Recent progress in this can be attributed to important advances, not least application dynamic chemistry. concept makes it possible start from readily...

Preference for polar adsorbates: The crystalline porous organic cage compound shown has an exceptional high surface area (1566 m2 g−1) and selective gas uptake. preferably adsorbs CO2 (9.4 wt %) over methane (0.98 %). Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted by the authors. Please note: publisher is responsible content functionality any supporting...

Abstract Recently, porous organic cage crystals have become a real alternative to extended framework materials with high specific surface areas in the desolvated state. Although major progress this area has been made, resulting compounds are restricted microporous regime, owing relatively small molecular sizes of cages, or collapse larger structures upon desolvation. Herein, we present synthesis shape‐persistent compound by reversible formation 24 boronic ester units 12 triptycene tetraol...

The interest in shape-persistent organic cages is nearly as old the supramolecular chemistry. In beginning, have often been synthesized a stepwise manner, which not only laborious but very also accompanied by low overall yields. 1988, MacDowell published one pot high-yielding synthesis of [2 + 3] imine based on TREN and aromatic dialdehydes, exploiting reversible condensation amines aldehydes to imines, was later used others make even larger basis resorcinarenes. 2008, characterization an...

Porosity makes powerful affinity materials for quartz crystal microbalances. The shape-persistent organic cages and pores create superior systems to existing ones direct tracing of aromatic solvent vapors. A shape size selectivity the analytes is observed. These can be processed thin films with highly reproducible sensing properties.

Abstract In recent years, the development of porous materials derived from discrete organic molecules made a substantial progress towards high‐surface‐area with distinct properties. One major advantage in comparison to existing, well‐established polymers is their solubility, making such compounds potential valuable precursors for “processing porosity”. important parameter specific surface area. The possibilities reach ultra‐high‐surface‐area this new type are critically discussed.

Abstract Discrete interlocked three‐dimensional structures are synthetic targets that sometimes difficult to obtain with “classical” approaches, and dynamic covalent chemistry has been shown be a useful method form such as thermodynamically stable products. Although defined hollow found in nature, for example, some viruses, similar have rarely synthesized on molecular level. Shape‐persistent organic cage compounds dimensions the nanometer regime now accessible high yields during...

An inherently chiral C3 -symmetric triaminotribenzotriquinacene was condensed in racemic and enantiomerically pure form with a bis(salicylaldehyde) to [2+3] salicylimine cage compounds. Investigations on the self-sorting revealed that while entropy favors narcissistic solution, selective social can be achieved by exploiting difference solubility between homochiral heterochiral cages. Gas sorption measurements further showed seemingly small structural differences have significant impact...

Anthropogenic greenhouse gases contribute to global warming. Among those gases, perfluorocarbons (PFCs) are thousands tens of times more harmful the environment than comparable amounts carbon dioxide. To date, materials that selectively adsorb in favor other less have not been reported. Here, a series porous organic cage compounds with alkyl-, fluoroalkyl-, and partially fluorinated alkyl groups is presented. Their isomorphic crystalline states allow study structure-property relationship...

A simple approach by reversible imine condensation to shape-persistent endo-functionalised nanocage compounds is presented.

Porous and highly ordered: After metal–organic frameworks (MOFs), which were first described over ten years ago, a new class of porous materials has been introduced: covalent organic (COFs), are distinguished by high thermostabilities, large specific surface areas, low densities. The example shows model structure COF-108.

Interior decorating: A post-synthetic method allows porous organic cage compounds to be prepared with functionalized interior cavities. The approach produces modified in quantitative yield and opens the possibility of preparing alloys different functionality. solution-based technique shows advantage solubility, an inherent property materials derived from discrete molecules.

The synthesis of various periphery-substituted shape-persistent cage compounds by twelve-fold condensation reactions four triptycene triamines and six salicyldialdehydes is described, where the substituents systematically vary in bulkiness. resulting were studied as permanent porous material nitrogen sorption measurements. When amorphous, steric demand cages exterior does not strongly influence gas uptake, BET surface areas approximately 700 m(2) g(-1) for all 3 c-e, independently In...

Abstract Ein Bereich der supramolekularen Chemie umfasst die Synthese diskreter dreidimensionaler Aggregate durch Koordination von Übergangsmetallen. Teil dieses Gebiets ist Käfigverbindungen, Knüpfung koordinativer Bindungen entstehen. Heute kennt man ein breites Spektrum solcher Koordinationskäfige. Relativ selten sind jedoch analoge organische aus kovalenten Bindungsbildungen resultieren. In letzter Zeit wurden auf diesem Gebiet einige wichtige Fortschritte erzielt, nicht zuletzt...

Abstract Recently, porous organic cage crystals have become a real alternative to extended framework materials with high specific surface areas in the desolvated state. Although major progress this area has been made, resulting compounds are restricted microporous regime, owing relatively small molecular sizes of cages, or collapse larger structures upon desolvation. Herein, we present synthesis shape‐persistent compound by reversible formation 24 boronic ester units 12 triptycene tetraol...

Abstract A highly soluble pyrene‐fused undecacene is realized by end‐capping the rectilinear aromatic π‐plane with triptycenylene units. Besides good solubility, compound shows a high tendency to crystallize. Two polymorphs from dichlorobenzene and chloroform are described. In polymorph chloroform, half of molecules strongly bent out 26.4°.

Abstract Polycyclic aromatic hydrocarbons (PAHs) that contain both five‐ and seven‐membered rings are rare, those where these annulated to each other build azulene units have, date, mainly been generated in minute amounts on surfaces. Herein, a rational approach synthesize soluble contorted PAHs containing two embedded the bulk is presented. By stepwise detachment of tert ‐butyl groups, series three with different degrees contortion has made study impact curvature aromaticity conjugation....

The bigger the better? Rigidity is more important than size for construction of permanent porous crystals from organic cage compounds. Two [2+3] compounds have been synthesized by an imine condensation reaction. one consisting rigid subunits (figure left) has accessible BET surface area 744 m2 g−1, whereas compound with flexible basically nonporous (BET area: 30 g−1) although shape-persistent cavity larger (9.8 vs. 7.8 Å).

Chiral self-sorting is intricately connected to the complicated chiral processes observed in nature and no artificial systems of comparably complexity have been generated by chemists. However, only a few examples purely organic molecules reported so far, where process could be controlled. Herein, we describe large cubic [8+12] salicylimine cage compounds based on TBTQ precursor. Out 23 possible isomers enantiopure meso were formed, which unambiguously characterized single crystal X-ray...

A contorted polycyclic aromatic hydrocarbon (PAH) in the shape of a monkey saddle has been synthesized three steps from readily available truxene precursor. The PAH is consisting five-, seven six-, and eight-membered rings unambiguously characterized by single-crystal X-ray diffraction. Owing to biaryl axes inherently chiral. inversion two enantiomeric structures into each other preferably occurs through twisting peripheral rather than fully planar intermediate, as calculated DFT methods....

Abstract Mechanically interlocked structures, such as catenanes and rotaxanes, are fascinating synthetic targets some used for molecular switches machines. Today, the vast majority of catenated structures built upon macrocycles only a very few examples three-dimensional shape-persistent organic cages forming have been reported. However, catenation in all these cases was based on thermodynamically favoured π – π- stacking under certain reaction conditions. Here, we show that catenane...

Mechanically interlocked structures are fascinating synthetic targets and the topological complexity achieved through catenation offers numerous possibilities for construction of new molecules with exciting properties. In structural space catenated organic cage molecules, only few examples have been realized so far, control over process in solution is still barely achieved. Herein, we describe formation a quadruply catenane giant chiral [8+12] salicylimine cubes. The could be controlled by...