Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

• Inaiá O. Rocha,
• Yuri G. Kappenberg,
• Wilian C. Rosa,
• Clarissa P. Frizzo,
• Nilo Zanatta,
• Marcos A. P. Martins,
• Isadora Tisoco,
• Bernardo A. Iglesias and
• Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

• trifluoromethylated hybrid system comprising the Schiff base scaffolds from some 6-aminoquinolines and salicylaldehyde derivatives in order to analyze and evaluate their photophysical, photostability, and antioxidant properties for possible future applications in the pharmacological areas or materials sciences

• VERTEX 70 spectrophotometer with Platinum ATR accessory (diamond crystal) in the 4000–400 cm−1 region. High-resolution mass spectra (HRMS) were obtained for all compounds on a hybrid high-resolution and high-accuracy (5 μL/L) micro Q-TOF mass spectrometer (Bruker Scientific®, Billerica, MA, USA) at the

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• subsequently frozen to prepare the cryogel, prior to freeze drying. While this approach offers less control over the process than that reported by Serex, Braschler and co-workers, it does not require the cold stage necessary for cryogelation to occur during printing. Hybrid collagen/chitosan bioinks have also

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162

• ) approach [71] at the restricted Becke, 3-parameter, Lee–Yang–Parr hybrid functional (B3LYP) with standard basis set 6-31G (d) were carried out. Experimental procedure for the Suzuki–Miyaura coupling and spectroscopic data for 9-chloro-2,4-diaryl-5,6,7,8-tetrahydroacridine derivatives 4a–g 2,4-Dibromo-9

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• [104]. The manganese(I)-catalyzed intermolecular alkenylation of tryptophan-containing peptides 32 was performed under basic conditions, yielding hybrid peptides 34 without racemization, containing a trans-alkene linker bearing biologically active motifs in chemo- and site-selective manners assisted by

• -NH tryptophan. Notably, alkenylative ligation of tryptophan-containing peptides and alkynes containing biomolecular motifs including sugar, menthol, or coumarin units was successful, delivering unprecedented hybrid complex peptides 34d–f in good yield. Based on the developed intermolecular process

Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions

• Susanne M. Fischer,
• Simon Renner,
• A. Daniel Boese and
• Christian Slugovc

Beilstein J. Org. Chem. 2021, 17, 1689–1697, doi:10.3762/bjoc.17.117

• TURBOMOLE program (version 7.4.1) [43]. Geometries were pre-optimized using the PBE [44] functional, the def2-SVPD [45][46] basis set and D3 [47] dispersion correction. All structures were then re-optimized using the hybrid functional B3LYP [48][49][50][51] D3 with the def2-TZVPPD basis set. For gas-phase

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• equilibrium conformer at ground state was first found at AM1 level. Then, further optimizations through density functional theory (DFT) approach [73] at the restricted Becke3–Lee–Yang–Parr hybrid functional (B3LYP) with standard basis set 6-31G were carried out. Experimental procedure and spectroscopic data

Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes

• Suraj Patel,
• Tyson N. Dais,
• Paul G. Plieger and
• Gareth J. Rowlands

Beilstein J. Org. Chem. 2021, 17, 1518–1526, doi:10.3762/bjoc.17.109

• . ESIMS was recorded on a Dionex UltiMate 3000. High-resolution mass spectrometry was performed using a ThermoScientific Q Exactive Focus Hybrid Quadrupole-Orbitrap mass spectrometer or a Bruker Daltonics MicrOTOF spectrometer. Infrared spectroscopy of compounds was completed on a ThermoFisher Nicolet iS5

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

• was well accommodated in a hybrid DNA:RNA duplex and stabilized bulged duplex and three way junctions [45]. The potential of the double-headed nucleoside 19 in secondary nucleic acid structures was compared with the earlier reported monomer 11 and found to be inferior to double-headed nucleoside 11

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• 0.2–0.8 °C in the thermal stability of RNA/DNA hybrid duplexes for each AM1 modification [11][78]. NMR structural studies have shown that the AM1 modification is well tolerated in an RNA duplex, with little effect on the global structure [79]. Furthermore, siRNA duplexes with amide modifications at

• increase in silencing activity for AM1-modified siRNAs with amide linkages at specific sites [75]. Structural insight into this observation was obtained using the crystal structure of the complex between Bacillus halodurans RNase H and the r(GAC ACC UGA UAM1UC) - d(GAA TCA GGT GTC) hybrid duplex [73

• modification has been attractive in antisense therapeutics as these altered oligonucleotides can form a hybrid duplex with unmodified RNA, which is recognized by RNase H [89][90]. While the thermal stability of PS2-modified RNA duplexes slightly decreases compared to the unmodified duplex, there is an increase

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

• Ke Wu,
• Yichen Ling,
• An Ding,
• Liqun Jin,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

• incomparable chelating ability towards selected transition metals, and the corresponding complexes were applied in various areas such as chemical-sensor materials, tunable redox-potential complexes, polymer hybrid luminescence materials, building blocks for multinuclear complexes, and as catalysts for cross

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• . For example, fullerene-containing materials are used as electron-withdrawing components and buffer layers in the development and design of photoconductors [41][42], supercapacitors [43][44], field effect transistors (FET) [45][46], organic light-emitting diodes (OLEDs) [47][48] and organic or hybrid

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• not require the preparation of 1-aminoalkylphosphonic acid or 1-aminoalkylphosphonous acid derivatives first as starting materials (Scheme 28) [42]. Similarly, phosphinopeptides [45][46], phosphinodepsipeptides [47], and hybrid sulfonophosphinopeptides [48][49] were prepared from amino amides and 2

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

• Vladislav A. Budevich,
• Sergei V. Voitekhovich,
• Alexander V. Zuraev,
• Vadim E. Matulis,
• Vitaly E. Matulis,
• Alexander S. Lyakhov,
• Ludmila S. Ivashkevich and
• Oleg A. Ivashkevich

Beilstein J. Org. Chem. 2021, 17, 385–395, doi:10.3762/bjoc.17.34

• –vis spectra and charge transfer were carried out within density functional theory for ground states and time-dependent density functional theory (TD-DFT) for excited states using the τ-dependent hybrid tHCTHhyb functional [37] with the 6-311+G(2d,p) basis set [38]. The chosen functional allows to

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

• Minzan Zuo,
• Krishnasamy Velmurugan,
• Kaiya Wang,
• Xueqi Tian and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

• with various macrocyclic hosts as well as on the role of macrocyclic-hosts-assisted hybrid materials in energy transfer. To keep the clarity of this review, the macrocycles are categorized into the most commonly used supramolecular hosts, including crown ethers, cyclodextrins, cucurbiturils

• , calixarenes, and pillararenes. This minireview not only summarizes the role that macrocycles play in photocatalytic reactions but also clarifies the photocatalytic mechanisms. Finally, the future research efforts and new pathways to apply macrocycles and supramolecular hybrid materials in photocatalysis are

• -dependent selective arrangement of one or two substrates within the cavity for photocatalysis. Therefore, this review will focus on: i) the role of the supramolecular system in mediating the photocatalytic selectivity, yield, and the rate of the photocatalytic products and ii) macrocycle-assisted hybrid

Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

• Daria I. Tonkoglazova,
• Anna V. Gulevskaya,
• Konstantin A. Chistyakov and
• Olga I. Askalepova

Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

• , we synthesized carbazole-based [6]helicenes fused with an azine ring (quinoxaline, pyrazine or pyridine ones). Scheme 2 represents the current work. We envisaged that combining the carbazole unit with the readily available azine building block would result in the formation of donor–acceptor hybrid

• quinoxaline-fused hybrid 10a is intermediate (52.8° and 50.5°). Comparing the sum of the inner helix torsion angles of the helicenes 10a–c and 12 reveals the same patterns. Evidently, the repulsive interaction of the H(14) and H(g) atoms of 10c is the main reason for the observed extra twisting, whereas

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• synthesised by NRPS gene clusters (surfactin, plipastatin, and bacillibactin) and one by a hybrid NRPS–PKS gene cluster (bacillaene, Figure 1). The well-studied biosurfactant surfactin, encoded by the srfAA-AD gene cluster, reduces the surface tension needed for swarming and sliding motility [38][39]. The

• incubated at 30 °C with continuous shaking (548 cpm, 2 mm), and the OD600 was measured in 15 min intervals over 24 h. All graphical visualisations were prepared using ggplot2 [79]. Overview of the NRPs surfactin, plipastatin, bacillibactin, and iturin as well as the hybrid NRP-PK bacillaene produced by

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

• Jonas Becher,
• Daria V. Berdnikova,
• Heiko Ihmels and
• Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

• temperature than the other ones. Most notably, the representative DNA denaturation analysis with ligand 4e and different quadruplex forms clearly reveals a significant selectivity. Hence, the hybrid antiparallel G4-DNA 22AG as well as the parallel quadruplex-forming KRAS sequence are stabilized to a

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

• Viola Kolaříková,
• Markéta Rybáčková,
• Martin Svoboda and
• Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

• internal standards. Chemical shifts are given in parts per million and coupling constants in hertz. Mass spectra (ESI, APCI) and HRMS spectra were measured with a hybrid LTQ Obitrap XL instrument (Thermo Fisher Scientific). All reactions were performed in a dry inert atmosphere (Ar) in oven-dried flasks

Encrypting messages with artificial bacterial receptors

• Pragati Kishore Prasad,
• Naama Lahav-Mankovski,
• Leila Motiei and
• David Margulies

Beilstein J. Org. Chem. 2020, 16, 2749–2756, doi:10.3762/bjoc.16.225

• during bacterial growth. The emission spectra of the bacterial samples labeled with the three DNA-based receptors were recorded using black flat-bottom 384-well microplates (Corning) and a BioTek synergy H4 hybrid multiwell plate reader. The fluorescence responses were measured using excitation

Leveraging glycomics data in glycoprotein 3D structure validation with Privateer

• Haroldas Bagdonas,
• Daniel Ungar and
• Jon Agirre

Beilstein J. Org. Chem. 2020, 16, 2523–2533, doi:10.3762/bjoc.16.204

• containing glycans that were previously unreported and inconsistent with glycan biosynthetic pathways. In particular, the model contained oligosaccharide chains with Man-(1→3)-GlcNAc and GlcNAc-(1→3)-GlcNAc linkages, β-galactosyl motifs capping oligomannose-type glycans and hybrid-type glycans containing

Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction

• Tony Jin,
• Malickah Hicks,
• Davis Kurdyla,
• Sabahudin Hrapovic,
• Edmond Lam and
• Audrey Moores

Beilstein J. Org. Chem. 2020, 16, 2477–2483, doi:10.3762/bjoc.16.201

• parameters were performed on PdCl2 and either ChNC or ChsNC, but with no H2 reductant. In this case, the solution color remained yellow, indicating that using either ChNC or ChsNC alone cannot fully reduce PdCl2. The resulting hybrid materials are noted PdNP@ChNC and PdNP@ChsNC, respectively. Dihydrogen was

Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

• Tatsuhiro Uchikura,
• Nanami Kamiyama,
• Taisuke Ishikawa and
• Takahiko Akiyama

Beilstein J. Org. Chem. 2020, 16, 2442–2447, doi:10.3762/bjoc.16.198

• diamine ligandsa. Supporting Information Supporting Information File 480: Details of screening experiments, synthetic procedures and characterization data of new compounds, and copies of spectra. Funding JSPS KAKENHI Grant Numbers JP17H03060, JP20H00380, and JP20H04826 (Hybrid Catalysis)

Recent developments in enantioselective photocatalysis

• Callum Prentice,
• James Morrisson,
• Andrew D. Smith and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197