Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• indicated that structurally diverse polymers formed by different polymerization mechanisms can readily be linked just by a simple NIR-induced CuAAC reaction. The macromolecular scope was further extended to the preparation of cross-linked materials. Thus, the formulations containing bisphenol A di(3-azido-2

• = 93%. 1H NMR (500 MHz, DMSO-d6) δ 8.70 (s, 1H), 8.44 (dd, 2H), 8.14 (dd, 2H), 7.64 (td, 2H), 7.56 (td, 2H), 5.51 (s, 2H); 13C{1H} NMR (DMSO-d6, 125 MHz) δ 131.39, 130.72, 129.51, 129.06, 127.28, 126.96, 125.88, 124.51, 45.96. Synthesis of bisphenol A di(3-azido-2-hydroxypropan-1-ol) ether (Az-3

• ) Diazido monomer, bisphenol A di(3-azido-2-hydroxypropan-1-ol) (Az-3) was synthesized according to a described method [46]. Az-3 was obtained as light yellowish viscous oil and was directly used without further purification, yield 98%. 1H NMR (500 MHz, CDCl3) δ 7.15 (m, 4H), 6.82 (m, 4H), 4.16 (m, 2H), 4.0

Valorisation of plastic waste via metal-catalysed depolymerisation

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

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• -isosorbide) terephthalate, can replace polyethylene terephthalate (PET) [7]. In the production of polycarbonate and epoxy resins, the physicochemical properties of isosorbide allow the replacement of bisphenol A by this bio-based molecule [8][9]. At an industrial level, isosorbide is produced from the double

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

• of Science and Technology, Nanjing 210094, China 10.3762/bjoc.13.211 Abstract We successfully employed bisphenol A and several different formyl-containing monomers as useful building blocks to construct a series of hydroxy-group-containing porous organic polymers in a sealed tube at high temperature

• : bisphenol A; carbon dioxide uptake; hydrogen storage; OH-containing; porous organic polymers; Introduction Porous organic polymers standing out from kinds of porous materials such as zeolite, activated carbon, metal-organic frameworks [1][2], and covalent organic frameworks [3][4], with their prominent

• produce a series of porous polymers. In this contribution, bisphenol A (BPA) was employed as a novel polyphenol monomer instead of phloroglucinol. BPA is a commercially available industrial raw material, which is much cheaper than phloroglucinol. In addition, BPA might be stored more easily, compared with

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• freedom and also to form smaller ring sizes [81]. Templated oligosaccharide synthesis Recently, Demchenko and co-workers introduced templated oligosaccharide synthesis, wherein bisphenol A (BPA) was used as the template and succinoyl, glutaryl or phthaloyl linkers were used to tether glycosyl donors and

Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• . RIs of 1 and 4 are thus close to that of aromatic crosslinkers such as ethoxylated bisphenol-A dimethacrylate, EBPADMA (2 ethoxy groups, nD20 1.525, η ≈ 900 mPa·s), but at a significantly lower viscosity and with the important difference, that all double bonds can take part in polymerization reactions

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• bisphenol A was enhanced in aqueous solutions containing β-CD [25], while the photodecomposition of pesticides of similar structure (parathion and paraoxon) was inhibited or catalyzed, respectively, by β-CD [26]. The complex formation can either protect the drug from the effect of light or accelerate the

• photodegradation of methylene blue [24], and CD-functionalized Fe3O4/TiO2 was efficient catalyst in photodecomposition of endocrine disrupting compounds, such as bisphenol A and dibutyl phthalate [30]. Producing strong oxidizing radicals (hydroxyl and superoxide radical ions) titanium dioxide is a widely used

Isosorbide and dimethyl carbonate: a green match

• Fabio Aricò and
• Pietro Tundo

Beilstein J. Org. Chem. 2016, 12, 2256–2266, doi:10.3762/bjoc.12.218

• bisphenol A in polycarbonate preparation. In this view, the main issue that limits the exploitation of this compound is its lower acidity. To overcome this problem, polycarbonates incorporating an isosorbide moiety have been synthesized via a chlorine-based approach, i.e., employing phosgene or its

Superstructures with cyclodextrins: chemistry and applications III

• Gerhard Wenz and
• Eric Monflier

Beilstein J. Org. Chem. 2016, 12, 937–938, doi:10.3762/bjoc.12.91

• styrene from ethylbenzene [3][4]. Highly porous networks were synthesized by crosslinking β-CD with tetrafluoroterephthalonitrile. These networks were able to almost completely remove pollutants (e.g., bisphenol A) within a short time from wastewater [5]. Stimuli-responsive nanoparticles were assembled by

Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations

• Sebastian Reinelt,
• Monir Tabatabai,
• Urs Karl Fischer,
• Norbert Moszner,
• Andreas Utterodt and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1733–1740, doi:10.3762/bjoc.10.180

• synthesis of the phenol-based thiols (10a,b, 14a–c, 17) was accomplished by the radical addition of thioacetic acid to suitable allyl-modified precursors as depicted in Scheme 1 and Scheme 2. For the synthesis of 10a and 10b the well-established hydroxymethylation of bisphenol A was the starting point of

• etherification, which was conducted in analogy to a procedure described in literature [40], as demonstrated in Scheme 2. Bisphenol A, bisphenol S and the trisphenol derivative 1,1,1-tris(4-hydroxyphenyl)ethane were chosen as basic structures. Subsequently, the successful radical addition of thioacetic acid (8

• . Surprisingly, no significant effect of the degree of functionalization (four versus six thiol groups) on the mechanical properties of the cured sample was observed while comparing 14a and 17. Regarding 14a and 14b, no significant effect was found by changing the backbone from bisphenol A to bisphenol S

N,N'-(Hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide): Synthesis via cyclodextrin mediated N-alkylation in aqueous solution and further Prilezhaev epoxidation

• Julian Fischer,
• Simon Millan and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2834–2840, doi:10.3762/bjoc.9.318

• ; rheology; sulfonamides; Introduction Various diepoxides easily react with amines or diamines to form cross-linked, cyclic or linear addition-polymers, which are implemented in construction, electronic, aerospace, medical and dental industries [1][2]. Hereby, bisphenol A diglycidyl ether (BADGE) is often

• used [3][4]. However, non-bisphenol A based diepoxides are subject to intensive research [5][6][7][8][9]. The industrial synthesis of BADGE and other commercially available diepoxides proceeds mainly by using epichlorohydrin, whereby usually several side products and oligomers are formed in significant

• , whereby water solubility of 3 and 4 were increased by adding β-CD and α-CD, respectively. By applying oscillatory rheological measurements, a mixture of 6 and 8 reached the gelpoint after about 40 to 45 min at 50 °C. Thus, an environmentally more sustainable route for the synthesis of a bisphenol A free

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

• Jiří Kulhánek and
• Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

• and co-workers reported the synthesis of epoxy-based nonlinear optical polymers 144 functionalized by post-azo coupling (Figure 23; [130]). The parent polymer backbone was synthesized from diglycidyl ether of bisphenol A and aniline and was further functionalized by diazotized amine 83 (Figure 15

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• such as 1,12-dodecanediol, bisphenol A, and/or neopentyl glycol, and the slow reacting isophorone diisocyanate (IPDI) were reacted in miniemulsion droplets [12]. Similar reactions were performed but in the presence of an organotin catalyst [101]. Relatively high apparent molecular weight polyurethane

Formation of epoxide-amine oligo-adducts as OH-functionalized initiators for the ring-opening polymerization of ε-caprolactone

• Julia Theis and
• Helmut Ritter

Beilstein J. Org. Chem. 2010, 6, 938–944, doi:10.3762/bjoc.6.105

• catalytic transfer hydrogenation. Accordingly, 4-nitroanisole was reduced under microwave conditions to give 4-aminoanisole which reacted immediately with the diglycidyl ether of bisphenol A in an addition polymerization reaction to yield oligo(amino alcohol)s. The hydroxy groups of the new formed oligomers

• polymerization (ROP) of ε-caprolactone to construct a new class of graft copolymers. Results and Discussion Formation of epoxide-amine adducts Epoxide-amine adducts based on diglycidyl ether of bisphenol A (1) and 4-aminoanisole (3) were synthesized in a MW-assisted one-pot reaction. Thus, 4-nitroanisole (2) was

• oligomeric initiator. This oligomer can be obtained in a one-pot microwave assisted heterogeneous catalytic transfer hydrogenation, starting from 4-nitroanisole (2) in the presence of the diglycidyl ether of bisphenol A (1). Product 4 consists of oligomers because of some side reactions. The hydroxy groups

Synthesis, characterization and photoinduced curing of polysulfones with (meth)acrylate functionalities

• Cemil Dizman,
• Sahin Ates,
• Lokman Torun and
• Yusuf Yagci

Beilstein J. Org. Chem. 2010, 6, No. 56, doi:10.3762/bjoc.6.56

• formation of the new ester carbonyl peak at around 1735 cm−1 (Figure 1). The structures of the macromonomers were further confirmed by 1H NMR analysis. As can be seen from Figure 2, where the 1H NMR spectra of the precursor polymer and telechelics are presented, the methyl group belonging to bisphenol A

• important components of UV curable formulations for obtaining networks that could have application in coatings and membranes. Experimental Materials Bisphenol A and bis(p-chlorophenyl) sulfone (Hallochem Pharma Co. Ltd, China), methanol (Merck), dimethylacetamide (DMA, 99%, Merck) were used without any

• determined using polystyrene standards. Thermal gravimetric analysis (TGA) was performed on Perkin–Elmer Diamond TA/TGA with a heating rate of 10 °C min under nitrogen flow. Preparation of the oligomers General procedure for the synthesis of polysulfone oligomer Bisphenol A (40 g, 175 mmol), bis(p