Effect of ring size on photoisomerization properties of stiff stilbene macrocycles

• Sandra Olsson,
• Óscar Benito Pérez,
• Magnus Blom and
• Adolf Gogoll

Beilstein J. Org. Chem. 2019, 15, 2408–2418, doi:10.3762/bjoc.15.233

• well-established reactions (Scheme 2). The indanone is formed by intramolecular Friedel–Crafts acylation of 2 under microwave radiation as reported by Oliverio et al. [23]. The second step is the demethylation of indanone methyl ether 3 by aluminium trichloride in toluene at reflux [24]. Two indanone

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• . Crystal data: The crystal structure of compound 9a was measured on an Xcalibur-3 diffractometer (graphite monochromated Mo Kα radiation, CCD detector, ω-scanning). The structure was solved by the direct method using the SHELXTL package [34][35]. Full-matrix least-squares refinement against F2 in

Excited state dynamics for visible-light sensitization of a photochromic benzil-subsituted phenoxyl-imidazolyl radical complex

• Yoichi Kobayashi,
• Yukie Mamiya,
• Katsuya Mutoh,
• Hikaru Sotome,
• Masafumi Koga,
• Hiroshi Miyasaka and
• Jiro Abe

Beilstein J. Org. Chem. 2019, 15, 2369–2379, doi:10.3762/bjoc.15.229

• interleaved pulse train (RIPT) method [37]. A picosecond laser, PL2210A (EKSPLA, 1 kHz, 25 ps, 30 μJ pulse−1 for 355 nm), and a supercontinuum (SC) radiation source (SC-450, Fianium, 20 MHz, pulse width: 50–100 ps depending on the wavelength, 450–2000 nm) were employed as the pump–pulse and probe sources

Aggregation-induced emission effect on turn-off fluorescent switching of a photochromic diarylethene

• Luna Kono,
• Yuma Nakagawa,
• Ayako Fujimoto,
• Ryo Nishimura,
• Yohei Hattori,
• Toshiki Mutai,
• Nobuhiro Yasuda,
• Kenichi Koizumi,
• Satoshi Yokojima,
• Shinichiro Nakamura and
• Kingo Uchida

Beilstein J. Org. Chem. 2019, 15, 2204–2212, doi:10.3762/bjoc.15.217

• Science, the University of Tokyo, 4-6-1, Komaba, Meguro-ku, Tokyo 153-8505, Japan Japan Synchrotron Radiation Research Institute, 1-1-1 Kouto, Sayo-cho, Sayo-gun, Hyogo 679-5198 Japan Nakamura Laboratory, RIKEN Cluster for Science, Technology and Innovation Hub, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

• JP26107012 in Scientific Research on Innovative Areas “Photosynergetics”, the CREST program (JPMJCR17N2) of the Japan Science and Technology Agency. We thank Ms Y. Nishikawa (NAIST) for conducting the mass-spectroscopic measurement. The synchrotron radiation experiments were performed using the BL40XU

• beamlines of SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal No. 2019A1110).

Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• specimen from an environment of interest. Experimental FIND The device was crafted from polyoxymethylene by the technical staff of the Helmholtz-Institute for Radiation- and Nuclear Physics, Nussallee 14–16, 53115 Bonn. The central plate (127 mm by 92 mm by 1 mm) and the two symmetrical upper and lower

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

• Christoph W. Grathwol,
• Nathalie Wössner,
• Sören Swyter,
• Adam C. Smith,
• Enrico Tapavicza,
• Robert K. Hofstetter,
• Anja Bodtke,
• Manfred Jung and
• Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

• and spectra. Upon exposure of 2b to radiation of 365 nm, changes in the UV–vis spectra proceeded slowly, due to the low absorbance of 2b in this wavelength region. However, shorter wavelengths, i.e. 254 nm, revealed fast and dramatic changes (Figure 2). After an initial decline and blue shift of the

• absorption maximum, the UV–vis spectrum of 2b developed a more complex structure with further illumination. The initial spectrum did not restore, neither thermally by standing in the dark nor photochemically when exposed to daylight. Regarding 2f, 254 nm radiation was obligatory to obtain changes in the UV

• –vis spectrum. However even long-term radiation did not lead to a complex spectrum as with 2b, yet no stationary state was reached in the examined time. As in the case of 2b, the spectrum of 2f was not altered by daylight, nor by standing several days in the dark at room temperature. LC–HRMS analysis

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• absorption of long wavelength UV radiation, thus the molecule appears yellow or red [2]. The size of this energy gap can be altered by EWG (−M effect) and EDG (+M effect) substituents (Figure 3), through decreasing or increasing the LUMO energy, respectively [1][2][3][6][7][42][62][67][71]. In some cases

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

• Arnault Heynderickx,
• Sébastien Nénon,
• Olivier Siri,
• Vladimir Lokshin and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

• 1112 instrument. HRMS was made at the Spectropole (http://fr-chimie.univ-amu.fr/spectropole/). The X-ray crystallography data were collected on a Bruker-Nonius KappaCCD diffractometer with CCD detector using Mo Kα radiation, λ = 0.71073 Å. Crystallographic data (excluding structure factors) for the

Tautomerism as primary signaling mechanism in metal sensing: the case of amide group

• Vera Deneva,
• Georgi Dobrikov,
• Aurelien Crochet,
• Daniela Nedeltcheva,
• Katharina M. Fromm and
• Liudmil Antonov

Beilstein J. Org. Chem. 2019, 15, 1898–1906, doi:10.3762/bjoc.15.185

• Kα1 radiation (λ = 1.54186 Å). The crystal was kept at 250(2) K during data collection by an Oxford Cryosystem open-flow cryostat. Using Olex2 [30], the structure was solved with the ShelXT [31] structure solution program using Intrinsic Phasing and refined with the ShelXL [31] refinement package

Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif

• Andrea Rodil,
• Alexandra M. Z. Slawin,
• Nawaf Al-Maharik,
• Ren Tomita and
• David O’Hagan

Beilstein J. Org. Chem. 2019, 15, 1441–1447, doi:10.3762/bjoc.15.144

• Spectrometer, operating in positive and negative mode, from solutions of the analyte in methanol or acetonitrile. The X-ray structure analysis of 7 (CCDC deposition code 1911894) was obtained using a Rigaku XtaLAB P200 diffractometer, using multi-layer mirror monochromed Mo Kα radiation. Structures of

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• interfaced to an Apollo II Dual ESI/MALDI source. Single crystals were analysed on a Bruker SMART APEX-II CCD diffractometer (λ(Mo Kα)-radiation, graphite monochromator, ω and 4 scan mode) and corrected for absorption using the SADABS program [53]. The structures were solved by direct methods and refined by

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

• Andrew T. King,
• Hugh G. Hiscocks,
• Lidia Matesic,
• Mohan Bhadbhade,
• Roger Bishop and
• Alison T. Ung

Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

• using IµS Incoatec Microfocus Source with Mo Kα radiation (λ = 0.710723 Å). The single crystal, mounted on the goniometer using a cryo-loop for intensity measurements, was coated with immersion oil type NVH and then quickly transferred to the cold nitrogen stream generated by an Oxford Cryostream 700

Bambusuril analogs based on alternating glycoluril and xylylene units

• Tomáš Lízal and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2019, 15, 1268–1274, doi:10.3762/bjoc.15.124

• -hydroxycinnamic acid (HCCA) matrix. Diffraction data were collected at 120 K on a diffractometer with graphite-monochromated Mo Kα radiation. Macrocycles 1a and 1b 2,4-Dimethylglycoluril (1.70 g, 10 mmol) and LiClO4 (1.06 g, 10 mmol) were suspended in dry THF (200 mL) under an Ar atmosphere. After addition of LiH

Mechanochemical synthesis of hyper-crosslinked polymers: influences on their pore structure and adsorption behaviour for organic vapors

• Sven Grätz,
• Sebastian Zink,
• Hanna Kraffczyk,
• Marcus Rose and
• Lars Borchardt

Beilstein J. Org. Chem. 2019, 15, 1154–1161, doi:10.3762/bjoc.15.112

• utilized and the resulting spectra were treated with ATR-correction by the OPUS 6.5 software. Powder X-ray diffraction (PXRD) patterns were collected in transmission geometry (MYTHEN 1K detector) with a STOE STADI P diffractometer operated at 40 kV and 30 mA with a Ge monochromator using Cu Kα1 radiation

Unexpected polymorphism during a catalyzed mechanochemical Knoevenagel condensation

• Sebastian Haferkamp,
• Andrea Paul,
• Adam A. L. Michalchuk and
• Franziska Emmerling

Beilstein J. Org. Chem. 2019, 15, 1141–1148, doi:10.3762/bjoc.15.110

• in the main text. The final products were characterized by XRPD. X-ray powder diffraction (XRPD): All samples were characterized by XRPD analysis using a Bruker D8 diffractometer with Cu-Kα1 radiation (λ = 1.54106 Å) in a range of 5.0° ≤ 2 θ ≤ 40°. The data were obtained in transmission mode with a

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• )°, b = 77.989(8)°, γ = 87.527(7)°, V = 1141.3(2) Å3, Mr = 479.45, Z = 2, space group , dcalc = 1.395 g/cm3, μ(Mo Ka) = 0.109 mm−1, F(000) = 496. Intensities of 8769 reflections (3910 independent, Rint = 0.027) were measured on the «Xcalibur-3» diffractometer (graphite monochromated Mo Kα radiation, CCD

• reflections (5089 independent, Rint = 0.060) were measured on the«Xcalibur-3» diffractometer (graphite monochromated Mo Kα radiation, CCD detector, ω-scaning, 2Θmax = 60°). The crystals of 16a (C28H24N4O2) are triclinic. At 293 K a = 8.322(3) Å, b = 9.563(6) Å, c = 16.053(5) Å, α = 94.08(4)°, β = 101.46(3

• )°, γ = 109.97(4)°, V = 1163.3(10) Å3, Mr = 448.53, Z = 2, space group , dcalc = 1.2804 g/cm3, μ(Mo Ka) = 0.083 mm−1, F(000) = 472. Intensities of 12048 reflections (3968 independent, Rint = 0.167) were measured on the «Xcalibur-3» diffractometer (graphite monochromated Mo Kα radiation, CCD detector, ω

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

• Leon Buschbeck,
• Aleksandra Markovic,
• Gunther Wittstock and
• Jens Christoffers

Beilstein J. Org. Chem. 2019, 15, 981–991, doi:10.3762/bjoc.15.96

• spectra were recorded first among all spectra there is indication of radiation damage by the doublet at 163.3 eV in SAM 7 (Figure 3) [60][61][62]. This signal is not found in monolayers from SAM 3 (Figure 2). There is only one N 1s component at 399.3 eV which corresponds to all nitrogen atoms at both SAMs

• obtained from the O 1s, F 1s, N 1s, C 1s and S 2p region with a pass energy of 30 eV, a step size of 0.05 eV and 50 ms dwell time. In order to avoid radiation damage of the SAMs, which becomes evident by the appearance of a second S 2p doublet at 163.3 eV/164.5 eV [60][61][62], 35 scans were averaged from

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• (NIR) photons are excellent light sources in physiological studies as this wavelength of light is less harmful to living tissue than ultraviolet irradiation. Deeper penetration of NIR photons into biological samples is possible using NIR radiation with wavelengths of 650–1050 nm (= 27–44 kcal mol−1

Coordination chemistry and photoswitching of dinuclear macrocyclic cadmium-, nickel-, and zinc complexes containing azobenzene carboxylato co-ligands

• Jennifer Klose,
• Tobias Severin,
• Peter Hahn,
• Alexander Jeremies,
• Jens Bergmann,
• Daniel Fuhrmann,
• Jan Griebel,
• Bernd Abel and
• Berthold Kersting

Beilstein J. Org. Chem. 2019, 15, 840–851, doi:10.3762/bjoc.15.81

• and mounted on the tip of a glass fiber. The data sets were collected at 213(2) K or 200 K (7) using a STOE IPDS-2T diffractometer equipped with graphite monochromated Mo Kα radiation (0.71073 Å). Table S7 in Supporting Information File 1 lists selected crystallographic data. The intensity data were

Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

• Rodrigo Abonia,
• Luisa F. Gutiérrez,
• Braulio Insuasty,
• Jairo Quiroga,
• Kenneth K. Laali,
• Chunqing Zhao,
• Gabriela L. Borosky,
• Samantha M. Horwitz and
• Scott D. Bunge

Beilstein J. Org. Chem. 2019, 15, 642–654, doi:10.3762/bjoc.15.60

• . A crystal was mounted onto a fiber from FluorolubeTM and was placed under a liquid N2 cooled stream, on a Bruker AXS diffractometer updated with an APEX II CCD detector. The radiation used was graphite monochromatized Mo Kα radiation (λ = 0.7107 Å). Lattice determination, data collection, structure

Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

• Pedro N. Batalha,
• Luana da S. M. Forezi,
• Maria Clara R. Freitas,
• Nathalia M. de C. Tolentino,
• Ednilsom Orestes,
• José Walkimar de M. Carneiro,
• Fernanda da C. S. Boechat and
• Maria Cecília B. V. de Souza

Beilstein J. Org. Chem. 2019, 15, 388–400, doi:10.3762/bjoc.15.35

• temperature, using a microfocus X-ray source using Mo Kα radiation (λ = 0.71073 Å). The crystal was mounted on a Kappa goniometer. Reflections were collected at room temperature, using a PHOTON 100 detector, which uses a CMOS sensor. Data collection and cell refinement were performed with the Bruker

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• ., iodonium salt). Thus, promising photoinitiating systems using Ir complexes have been proposed for polymerization under household fluorescence bulbs and even under sun radiation (useful for development of green technologies) [54]. Despite the really interesting properties of Ru and Ir complexes, they have

MoO₃ on zeolites MCM-22, MCM-56 and 2D-MFI as catalysts for 1-octene metathesis

• Hynek Balcar,
• Martin Kubů,
• Naděžda Žilková and
• Mariya Shamzhy

Beilstein J. Org. Chem. 2018, 14, 2931–2939, doi:10.3762/bjoc.14.272

• temperature for 3 h. The supports were characterized by XRD (Bruker AXS D8 Advance diffractometer with a graphite monochromator and a Vantec-1 position sensitive detector using Cu Kα radiation in Bragg−Brentano geometry) and by N2 adsorption (77 K, Micromeritics GEMINI II 2370 volumetric Surface Area Analyzer

Bioinspired cobalt cubanes with tunable redox potentials for photocatalytic water oxidation and CO₂ reduction

• Zhishan Luo,
• Yidong Hou,
• Jinshui Zhang,
• Sibo Wang and
• Xinchen Wang

Beilstein J. Org. Chem. 2018, 14, 2331–2339, doi:10.3762/bjoc.14.208

• TECNAIG2F20 instrument. Powder X-ray diffraction (XRD) patterns were collected on Bruker D8 Advance diffractometer with Cu K1 radiation (λ = 1.5406 Å). Photocatalytic test for water oxidation system [69]: Photocatalytic O2 production was carried out in a Pyrex top-irradiation reaction vessel connected to a

Novel photochemical reactions of carbocyclic diazodiketones without elimination of nitrogen – a suitable way to N-hydrazonation of C–H-bonds

• Liudmila L. Rodina,
• Xenia V. Azarova,
• Jury J. Medvedev,
• Dmitrij V. Semenok and
• Valerij A. Nikolaev

Beilstein J. Org. Chem. 2018, 14, 2250–2258, doi:10.3762/bjoc.14.200

• 1c (CCDC 1584937) and 2b (CCDC 1584938) an Agilent Technologies «Xcalibur» diffractometer with monochromated MoKα radiation was used. All samples were measured at 100 K. The unit cell parameters were refined by least square techniques in CrysAlisPro (Agilent Technologies, 2012) program complex