Novel approach to hydroxy-group-containing porous organic polymers from bisphenol A

• Tao Wang,
• Yan-Chao Zhao,
• Li-Min Zhang,
• Yi Cui,
• Chang-Shan Zhang and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 2131–2137, doi:10.3762/bjoc.13.211

• , indicating the degradation of BPA catalyzed by TSA at high temperature [29][30]. Nitrogen sorption measurements were employed to evaluate the porosity of the obtained polymers. The nitrogen adsorption–desorption isotherms of PPOP-1–PPOP-3 are similar to each other (Figure 3a). All of the isotherms show a

• crucial factor that influences the amount of adsorbed CO2, whereas the uptake capacity is more depended on porosity characteristic such as pore size in the networks [36][37]. Specially, the smallest pores contribute most to the CO2 uptake at low pressure [36]. Hence, PPOP-3 with a smaller pore size

• of bisphenol-A-based porous organic polymers. Porosity properties of PPOP-1–PPOP-3. Gas adsorption uptake of PPOP-1–PPOP-3. Supporting Information Supporting Information File 318: Experimental, instruments section, SEM images, data of TGA, FTIR and BET surface area, virial analysis of the adsorption

Mechanochemistry-assisted synthesis of hierarchical porous carbons applied as supercapacitors

• Desirée Leistenschneider,
• Nicolas Jäckel,
• Felix Hippauf,
• Volker Presser and
• Lars Borchardt

Beilstein J. Org. Chem. 2017, 13, 1332–1341, doi:10.3762/bjoc.13.130

• designing the porosity of carbon materials involves hard or soft templates [22][23][24]. Hard-templating utilizes metal oxide nanoparticles [25] and salts [26][27][28], which have to be synthesized in advance. Soft-templating employs surfactants or other structure-directing molecules, which self-assemble to

• supported by EDX measurements (Table 1), showing a Ti content below the detection limit. The pore structure of the materials was analyzed by nitrogen physisorption (Figure 5A). Neither the polymer (Polymer-SF-3) nor the carbonized composite material (Comp-SF-3) show a significant porosity (Table 1). This

• given in Table S1 in Supporting Information File 1. We further investigated the influence of the EG to CA ratio on the porosity of the material, while keeping the TIPP to CA ratio constant (1:1). The pore volume increased with a higher content of ethylene glycol from 1.34 cm3 g−1 for a ratio of 1:1 to

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• porosity, processing-dependence of final properties etc.) and the size of ‘materials space’ is consequently much larger than that of ‘drug-like’ space. This recognition has accelerated the development of very high throughput synthesis and characterization methods for materials, and spawned the application

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• to tune the porosity. These obtained polymers exhibit microporous and mesoporous features. The highest Brunauer–Emmett–Teller specific surface area for the resulting polymers was found to be 1220 m2 g−1, and the related carbon dioxide storage capacity was found to be 14.4 wt % at 1.0 bar and 273 K

• a polymer network with a high SSA [6], HCPs with knitted building blocks have been widely utilized because of their high SSA [7][8], mild synthesis conditions [9][10], and wide range of monomers [11]. The porosity and functionality of HCPs is highly dependent on the core structural monomers [12][13

• microporous HCPs based on carbohydrates for carbon dioxide capture and storage by hydrogen bonding and dipole–quadrupole interactions [17]. The reported pore-size distribution (PSD) and related porosity tuning are in the range of micropore size. Considering that the polyhydroxylated and chiral structure

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• support material, e.g., acid/base properties [184][185], morphology, grain size [186], porosity [187], strong metal–support interactions, swelling propensity [188]). In propyne hydrogenation, for instance, catalyst resistance was shown to decrease with increasing acidity of the support [189]. In order to

Fast and efficient synthesis of microporous polymer nanomembranes via light-induced click reaction

• Qi An,
• Youssef Hassan,
• Xiaotong Yan,
• Peter Krolla-Sidenstein,
• Tawheed Mohammed,
• Mathias Lang,
• Stefan Bräse and
• Manuel Tsotsalas

Beilstein J. Org. Chem. 2017, 13, 558–563, doi:10.3762/bjoc.13.54

• microporous polymers (CMPs) are materials of low density and high intrinsic porosity. This is due to the use of rigid building blocks consisting only of lightweight elements. These materials are usually stable up to temperatures of 400 °C and are chemically inert, since the networks are highly crosslinked via

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• thereby the spacing of the frameworks can be controlled and for the most elongated derivative, continuous channels are obtained within the structure. Stability, structural integrity and porosity of the material were investigated by powder X-ray diffraction, thermogravimetry and sorption measurements

• promising alternative thus combining low-weight materials with easy processing. However, the crystallization of stable organic structures possessing permanent porosity is still quite challenging and only a limited number of examples for supramolecular crystals based on hydrogen bonding [29][30][31][32][33

• ][34][35][36][37][38][39][40][41][42][43][44][45] or π–π-stacking [46] that retain porosity in the solid state under activation conditions have been reported so far. One possible way to enhance stability and shape-persistency might be the implementation of polyfunctional building blocks in order to

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification

• Anna Zaghi,
• Daniele Ragno,
• Graziano Di Carmine,
• Carmela De Risi,
• Olga Bortolini,
• Pier Paolo Giovannini,
• Giancarlo Fantin and
• Alessandro Massi

Beilstein J. Org. Chem. 2016, 12, 2719–2730, doi:10.3762/bjoc.12.268

• was then fabricated by packing a stainless steel column (10 cm length, 4.6 mm internal diameter) with PS-BEMP 5. Pycnometer measurements provided the hold-up volume Vo and the total porosity εtot of R5 [31], whereas the loaded amount of 5 was determined by weighing the filled and empty column. The

The weight of flash chromatography: A tool to predict its mass intensity from thin-layer chromatography

• Freddy Pessel,
• Jacques Augé,
• Isabelle Billault and
• Marie-Christine Scherrmann

Beilstein J. Org. Chem. 2016, 12, 2351–2357, doi:10.3762/bjoc.12.228

• . Using Equations 8,10 and 11, the mass of eluent can be expressed by: The void volume V0 is connected to the column volume VC by the porosity of the silica ( = 0.9) and the volume of the column depends on the mass and density ( = 0.5) of the silica according to Equation 13 and Equation 14. We can then

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• the monomers is essential since the porosity, a desired feature, is best achieved by structurally interlocked motifs. In industrial applications, porous polymers have to meet several important criteria like high porosity, chemical and thermal stability while also possessing application-specific

• microporous polymers (CMPs) [5]. Most of these networks have the advantage of high porosity, but they are all made through precious metal-catalyzed reactions, which elevates the synthesis cost and limits their mass production. Another type of C–C bonded porous networks are hypercrosslinked polymers (HCPs) [6

• formation of these structures do not allow obtaining free nitrile or amine functionalities. The most used strategy to install available functional groups on porous materials is through post-modification, which often requires several steps and harsh conditions, and yields low porosity [12][13]. The

Hydroxy-functionalized hyper-cross-linked ultra-microporous organic polymers for selective CO₂ capture at room temperature

• Partha Samanta,
• Priyanshu Chandra and
• Sujit K. Ghosh

Beilstein J. Org. Chem. 2016, 12, 1981–1986, doi:10.3762/bjoc.12.185

• ]. In terms of surface area, tuneable porosity and feasible host–guest interaction, MOFs have scored over other above mentioned porous materials [6]. But the less hydrolytic stability of metal-organic frameworks limits their real time application [7][8]. So the search for new materials having high

• synthesis, the cost-effective formaldehyde dimethyl acetal (FDA), FeCl3 and that organic small molecules can produce very low cost materials with high yield [28]. Hyper-cross-linking prevents the close packing of polymeric chains in this type of material to impart the intrinsic porosity. Hyper-cross-linked

• , a clear capsule-type of morphology was found in the FESEM (Figure 2d and Figure S6). After all characterizations and proper desolvation of both compounds, we investigated their porosity. First, we measured the N2 adsorption at 77 K. The N2 uptake for HCP-91 was found to be 595 mL/g, whereas that for

Cross-metathesis of polynorbornene with polyoctenamer: a kinetic study

• Yulia I. Denisova,
• Maria L. Gringolts,
• Alexander S. Peregudov,
• Liya B. Krentsel,
• Ekaterina A. Litmanovich,
• Arkadiy D. Litmanovich,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2015, 11, 1796–1808, doi:10.3762/bjoc.11.195

• measurements with PCOE are impossible since the solution is not filterable through a 220 nm porosity membrane. Taking into account that the melting temperature of PCOE is about 45 °C, we can relate aggregation in the PCOE solutions at 25 °C to the onset of crystallization. In any case, it makes no sense to

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

• Yunfei Wang and
• Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

• properties of the coordination polymer were investigated by infrared spectroscopy, cyclic voltammetry, powder X-ray diffraction, and differential scanning calorimetric analyses. Furthermore, the microscopic porosity and surface area of the Zn-TTFV coordination polymer were measured by nitrogen gas adsorption

• analysis, showing a BET surface of 148.2 m2 g−1 and an average pore diameter of 10.2 nm. Keywords: complexation; coordination polymers; porosity; redox activity; tetrathiafulvalene; Introduction Tetrathiafulvalene (TTF) has been widely applied as a redox-active building block in organic electronic

• structures in the solid state with certain microscopic porosity. To assess the porous properties of Zn-TTFV 8, nitrogen gas adsorption analysis was conducted at 77 K. The adsorption isotherm shown in Figure 5A indicates a Type-II adsorption behaviour. Application of the Brunauer–Emmett–Teller (BET) model

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• explained by a high porosity based on a 3-dimensional growth of these polymer films during the electropolymerization process [59][60]. After butyl modification the hydrophobic character remains constant (135 ± 2° after modification, Figure 5, middle), while we changed the surface polarity of the polymer

3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates

• Aneta M. Tomkiel,
• Adam Biedrzycki,
• Jolanta Płoszyńska,
• Dorota Naróg,
• Andrzej Sobkowiak and
• Jacek W. Morzycki

Beilstein J. Org. Chem. 2015, 11, 162–168, doi:10.3762/bjoc.11.16

• electrode was a Bioanalytical Systems platinum inlay (1 mm in diameter), the auxiliary electrode was a platinum mesh (contained in a glass tube with a medium porosity glass frit), and the reference electrode was Ag/0.1 M AgNO3 in acetonitrile. The potential of the electrode vs the ferrocene/ferricinium ion

Synthesis of nanodiamond derivatives carrying amino functions and quantification by a modified Kaiser test

• Gerald Jarre,
• Steffen Heyer,
• Elisabeth Memmel,
• Thomas Meinhardt and
• Anke Krueger

Beilstein J. Org. Chem. 2014, 10, 2729–2737, doi:10.3762/bjoc.10.288

• measurement) [19] and all amino groups anywhere in the sample. However, this does not mean that all these amino groups are accessible, e.g., for further coupling reactions due to agglomeration or porosity of the material. Furthermore, the cleavage of strongly bound organic moieties from the surface will occur

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• electrocarboxylation of other substrates Besides the electrocarboxylation of chloroacetonitrile, CO2 can also be incorporated electrocatalytically in acetonitrile itself. Such reaction was successfully conducted in a two-compartment cell divided by a medium porosity glass frit (Scheme 20). This is an interesting

Multichromophoric sugar for fluorescence photoswitching

• Stéphane Maisonneuve,
• Rémi Métivier,
• Pei Yu,
• Keitaro Nakatani and
• Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

• (700 rpm, monitoring by TLC), and poured into distilled water after cooling to room temperature. The precipitate was then filtred through a cellulose acetate filter (porosity 2 µm) under vacuum and washed with water, then purified by column chromatography using pure EtOAc, then EtOAc/acetone (gradient

• stirred at 110 °C during 15 min under microwave irradiation (700 rpm, monitoring by TLC). After cooling to room temperature, the reaction mixture was poured into 20 to 25 mL of distilled water. The precipitate was then filtred through cellulose acetate filter (porosity 2 µm) under vacuum and washed with

• . The precipitate was then filtred through a cellulose acetate filter (porosity 2 µm) under vacuum and washed with water, then purified by column chromatogrphy using EtOAc:ethanol (9:1) to give 66% of the desired compound (45.8 mg, 0.022 mmol) as a red solid; mp 181–183 °C; Rf = 0.53 (EtOAc/acetone = 4

Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions

• Phei Li Lau,
• Ray W. K. Allen and
• Peter Styring

Beilstein J. Org. Chem. 2013, 9, 2886–2897, doi:10.3762/bjoc.9.325

• the autoclave reactor. Residence time in the continuous flow reactors The volume of the unpacked 1 mm diameter reactors in the styrene and methyl acrylate reactions were 2.36 and 0.79 mL respectively. The reactors containing catalyst with packing were found to have a porosity of 0.80, so neglecting

• reaction out to a 3.9 mm internal diameter PFR. The 9 cm long reactor was packed with the catalyst and packing material and the reaction carried out under identical reaction conditions to those used in the 1 mm reactor. Accounting for the 0.80 porosity of the reactor filled with the packed catalyst, the

Flow synthesis of phenylserine using threonine aldolase immobilized on Eupergit support

• Jagdish D. Tibhe,
• Hui Fu,
• Timothy Noël,
• Qi Wang,
• Jan Meuldijk and
• Volker Hessel

Beilstein J. Org. Chem. 2013, 9, 2168–2179, doi:10.3762/bjoc.9.254

• calculate the mass transfer coefficient, porosity (ε) = 0.5 estimated, density (ρ) = 1024 kg/m3, viscosity of fluid (μ) = 0.00134 kg/ms and thermal conductivity (K) = 0.58 (W/m·K). The Reynolds number (Re) for a fluid flow through a bed of approximately spherical particles of diameter D can be calculated

Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions

• Trevor A. Hamlin and
• Nicholas E. Leadbeater

Beilstein J. Org. Chem. 2013, 9, 1843–1852, doi:10.3762/bjoc.9.215

• referenced to hexafluorobenzene (−164.9 ppm) [53]. Reactions were monitored by an Agilent Technologies 7820A Gas Chromatograph attached to a 5975 Mass Spectrometer or 1H NMR. Flash chromatography and silica plugs utilized Dynamic Adsorbants Inc. Flash Silica Gel (60Å porosity, 32-63 µm). Apparatus

Stability of SG1 nitroxide towards unprotected sugar and lithium salts: a preamble to cellulose modification by nitroxide-mediated graft polymerization

• Guillaume Moreira,
• Laurence Charles,
• Mohamed Major,
• Florence Vacandio,
• Yohann Guillaneuf,
• Catherine Lefay and
• Didier Gigmes

Beilstein J. Org. Chem. 2013, 9, 1589–1600, doi:10.3762/bjoc.9.181

• porosity of 0.2 µm. The column oven was kept at 40 °C, and the injection volume was 20 µL. One ResiPore Pre-column (50 mm, 4.6 mm) and two ResiPore columns (250 mm, 4.9 mm) from Polymer Laboratories were used in series. The system was calibrated by using polystyrene standards in the range 100–400,000 g·mol

Simple and rapid hydrogenation of p-nitrophenol with aqueous formic acid in catalytic flow reactors

• Rahat Javaid,
• Shin-ichiro Kawasaki,
• Akira Suzuki and
• Toshishige M. Suzuki

Beilstein J. Org. Chem. 2013, 9, 1156–1163, doi:10.3762/bjoc.9.129

• a Pd–Ag co-plated layer preferentially dissolved Ag, leaving pores behind. Figure 1c shows an SEM image of the porous Pd surface after removal of Ag, where numerous pores are observed. Direct determination of the porosity of the porous metal layer was difficult because it firmly adhered and resisted

New enzymatically polymerized copolymers from 4-tert-butylphenol and 4-ferrocenylphenol and their modification and inclusion complexes with β-cyclodextrin

• Adam Mondrzyk,
• Beate Mondrzik,
• Sabrina Gingter and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123, doi:10.3762/bjoc.8.238

• and are distributed over three main columns of porosity 10000, 1000 and 100 Å, and one column upstream of porosity 100 Å (type: Gel Sd plus). A 486 tunable absorbance detector (Waters) and a SFD RI 2000 differential-refractometer (Schambeck) were used as detectors. Calibration took place with

Self-assembled organic–inorganic magnetic hybrid adsorbent ferrite based on cyclodextrin nanoparticles

• Ângelo M. L. Denadai,
• Frederico B. De Sousa,
• Joel J. Passos,
• Fernando C. Guatimosim,
• Kirla D. Barbosa,
• Ana E. Burgos,
• Fernando Castro de Oliveira,
• Jeann C. da Silva,
• Bernardo R. A. Neves,
• Nelcy D. S. Mohallem and
• Rubén D. Sinisterra

Beilstein J. Org. Chem. 2012, 8, 1867–1876, doi:10.3762/bjoc.8.215

• -Ni/Zn/βCD presented smaller particles and a more homogeneous particle size distribution. Higher porosity for this MHM compared to Fe-Ni/Zn was observed by Brunauer–Emmett–Teller isotherms and positron-annihilation-lifetime spectroscopy. Based on the pKa values, potentiometric titrations demonstrated

• the free volume (ΔVf = 46 Å3). These results corroborate BET isotherm studies, which pointed out a greater porosity in the material prepared by using βCD. Potentiometric titrations Potentiometric titrations were recorded in order to determine the number of ionizable sites for the magnetic materials