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Search for "crystals" in Full Text gives 627 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthetic approach to borrelidin fragments: focus on key intermediates

  • Yudhi Dwi Kurniawan,
  • Zetryana Puteri Tachrim,
  • Teni Ernawati,
  • Faris Hermawan,
  • Ima Nurasiyah and
  • Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

Graphical Abstract
  • LiAlH4 in ether to form alcohol 40 (89%) (Scheme 3). The primary alcohol 40 was then converted to its iodide derivative 42 (89%), from which single crystals were obtained, and its structure was determined unequivocally by XRD crystallography. Iodide 42 was then reacted with sodium phenylsulfinate in DMF
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Published 12 Jun 2025

Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold

  • Henry S. T. Smith,
  • Ben Giuliani,
  • Kanchana Wijesekera,
  • Kah Yean Lum,
  • Sandra Duffy,
  • Aaron Lock,
  • Jonathan M. White,
  • Vicky M. Avery and
  • Rohan A. Davis

Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90

Graphical Abstract
  • undescribed amine analogues 2–15 were fully characterised following 1D/2D NMR, UV, and HRMS data analyses. X-ray crystallographic analysis of crystals obtained from the aminated products 2, 7, 10, and 15 are also reported here. The new library of amine-substituted triazolopyrazines was screened against the
  • with relevant position numbering. Crystals obtained for 2 were analysed by X-ray crystallographic studies and confirmed the NMR-based structure assignment. The crystal structure of 2 is shown as a thermal ellipsoid plot below (Figure 3). With a simplified approach for the synthesis of aminated
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Published 10 Jun 2025

Gold extraction at the molecular level using α- and β-cyclodextrins

  • Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

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  • expected tridimensional CD-MOF in the presence of KAuBr4 in aqueous solution. Instead, they self-assembled into unidimensional threads that aggregated into superstructures and formed, in less than one minute, needle-shaped crystals visible to the naked eye. In these crystals, the molecules of α-CD stacked
  • diffraction of single crystals (Figure 3), showing, for both 1:1 and 2:1 stoichiometries, cyanoaurate anions inside the host cavity and potassium cations interacting with hydroxy groups of adjacent cyclodextrins. The strong host–guest affinity and complex stability in the solution phase has been studied by
  • added to reach a final concentration of 0.25% (v/v). To better understand the role of DBC, crystals of the ternary complex β-CD·KAuBr4·DBC were obtained by slow vapor diffusion of DBC into an aqueous solution of KAuBr4 and β-CD over three days. Single-crystal diffraction showed the [AuBr4]− anion
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Published 06 Jun 2025

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

  • Krishna Pandey,
  • Lucas X. Orton,
  • Grayson Venus,
  • Waseem A. Hussain,
  • Toby Woods,
  • Lichang Wang and
  • Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

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  • further understand the complexation with metal cations, separate co-crystals of HIM 1 with LiBArF20 and NaBArF24 were obtained by vapor diffusion of diethyl ether into acetone. The details of the co-crystallization experiment are provided in the crystallographic information section of Supporting
  • Information File 1. Single crystals with quality suitable for XRD analysis were obtained in both cases (Figure 5). Unlike the previous assumption of metal coordination at the macrocycle core [17], the crystal structures reveal complexation of both cations at the periphery of the macrocycle. Both 1/LiBArF20
  • similar trend was seen in the HIM–Na+ crystals where complex 4 and complex 5 are similar in energy with a difference of less than 1.5 kJ/mol. While both Li+ and Na+ crystals were prepared in similar conditions, the difference in the resulting crystal structure (e.g., location of benzyl rings) could arise
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Published 30 May 2025

Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions

  • Wen-Hui Mi,
  • Teng-Yu Huang,
  • Xu-Dong Wang,
  • Yu-Fei Ao,
  • Qi-Qiang Wang and
  • De-Xian Wang

Beilstein J. Org. Chem. 2025, 21, 884–889, doi:10.3762/bjoc.21.72

Graphical Abstract
  • target ultracyclic hosts. The synthesized ultracycles were fully characterized by spectrometric and elemental analysis (Scheme 1 and Schemes S1‒S3 in Supporting Information File 1). Single crystals of B4aH were obtained by slow vapor diffusion of ethyl ether into an acetonitrile/chloroform 1:1 (v/v
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Published 06 May 2025

Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation

  • Zhihua Liu,
  • Ya-Zhi Chen,
  • Ji Wang,
  • Qingling Nie,
  • Wei Zhao and
  • Biao Wu

Beilstein J. Org. Chem. 2025, 21, 845–853, doi:10.3762/bjoc.21.68

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  • understand cooperative interactions between complexed ions, we tried to grow the crystal structure of studied salts. Fortunately, single crystals of Cs2CO3 and Cs3PO4 complexes were obtained by slow vapor diffusion from acetonitrile and diethyl ether. Notably, clearly stronger ion-dipole interactions of
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Published 29 Apr 2025

Development and mechanistic studies of calcium–BINOL phosphate-catalyzed hydrocyanation of hydrazones

  • Carola Tortora,
  • Christian A. Fischer,
  • Sascha Kohlbauer,
  • Alexandru Zamfir,
  • Gerd M. Ballmann,
  • Jürgen Pahl,
  • Sjoerd Harder and
  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2025, 21, 755–765, doi:10.3762/bjoc.21.59

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  • conditions. The product was isolated as colorless crystals in good yield of 81% (Scheme 1). Complex 4 crystallizes as a C2-symmetric chiral mononuclear complex in which Ca is bound to two monodentate phosphate ligands (Figure 1). Four MeOH ligands complete the slightly distorted octahedral coordination
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Published 14 Apr 2025

Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups

  • Christian Akakpo,
  • Peter Y. Zavalij and
  • Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55

Graphical Abstract
  • hydrophobic region of the guest which changes the orientation of Ha with respect to the magnetically shielding region [54][63][64]. X-ray crystal structure of C1 We were fortunate to obtain single crystals of the C1·Me6CHDA complex and solved the crystal structure by X-ray diffraction (CCDC 2411723). Figure 5
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Published 03 Apr 2025

Origami with small molecules: exploiting the C–F bond as a conformational tool

  • Patrick Ryan,
  • Ramsha Iftikhar and
  • Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

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  • stereoelectronic effects such as hyperconjugation and electrostatic attraction/repulsion. These fluorine-derived conformational effects have been exploited to control the shapes, and thereby enhance the properties, of a wide variety of functional molecules including pharmaceutical agents, liquid crystals
  • stereochemical change can have upon physical properties. Another functional context in which multivicinal fluoroalkanes have been explored is in liquid crystals [8][40]. Liquid crystalline materials require the molecules to be rod-shaped, and to have a dipole moment that is oriented perpendicular to the long
  • molecular properties. The fluorine–oxygen gauche effect has been exploited to influence the properties of liquid crystals [86][87]. For example, the vicinal fluoroether 50 (Figure 7) can adopt a low-energy conformation in which the terminal C–F bond aligns gauche to the vicinal C–O bond. This orientation of
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Published 02 Apr 2025

Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

  • Yuuki Ishii,
  • Minoru Yamaji,
  • Fumito Tani,
  • Kenta Goto,
  • Yoshihiro Kubozono and
  • Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53

Graphical Abstract
  • processes contributing to the low fluorescence quantum yield of the F8-phenacenes (cf. Table 1). Because fluorescence behavior in the solid state reflects molecular alignment and intermolecular interactions in the crystals, solid-state fluorescence of the F8-phenacenes was investigated. We observed
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Published 24 Mar 2025

Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters

  • Olesja Koleda,
  • Janis Sadauskis,
  • Darja Antonenko,
  • Edvards Janis Treijs,
  • Raivis Davis Steberis and
  • Edgars Suna

Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50

Graphical Abstract
  • NMR methods, and all attempts to obtain crystals suitable for X-ray crystallographic analysis were unsuccessful. N-Protected 2-aminoproline derivatives 6 are relatively stable under basic conditions as evidenced by successful hydrolysis of the ester moiety in 6a,d,e using aqueous LiOH to provide acids
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Published 19 Mar 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • colorless crystals from the reaction between Et3N and CH2Cl2 at 100 °C in DMF. Subsequently, the corresponding α-aminophosphonate 35a was obtained by heating 36a with an equal amount of diethyl phosphite (Scheme 28b). Furthermore, when the reaction was carried out with CD2Cl2, the corresponding deuterated
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Published 13 Mar 2025

Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

  • Long K. San,
  • Sebastian Balser,
  • Brian J. Reeves,
  • Tyler T. Clikeman,
  • Yu-Sheng Chen,
  • Steven H. Strauss and
  • Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

Graphical Abstract
  • crystals, addition of a drop of 1,2-dibromoethane). Only the addition of 1,2-dibromoethane enabled the generation of the Grignard reagent which was observed by bubbles and an instant increase of the reaction mixture’s temperature. CF2C6F5I (97.5 µL, 625 µmol) dissolved in dry THF (20 mL) was added with a
  • concentrations used for ANTH, 9,10-ANTH(BnF)2, and quinine sulfate were 1.89, 1.14, and 1.94 (10−5 M), respectively. Relative quantum yields were calculated using the following equation referenced to quinine sulfate (Φf = 0.55 in 0.1 M H2SO4): X-ray crystallography The diffraction-quality single crystals of 9
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Published 07 Mar 2025

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

  • Metodej Dvoracek,
  • Brendan Twamley,
  • Mathias O. Senge and
  • Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

Graphical Abstract
  • packing mode. Extra precautions were taken to shield the compounds from light during synthesis, purification, and storage. After crystallizing each bimane, a vial containing multiple crystals was selected for irradiation studies. Cl2B (B), which showed 5% presence of the [2 + 2] dimer after
  • ). Crystallographic bond length restraints and constraints were used in each model and bond lengths and angle accuracy are affected by the disorder model (see Supporting Information File 1 for further details). In the case of Cl2B (all crystals, Figure 5), the torsion angle between the two double bonds in the bimane
  • fluorescence spectrum and η is the refractive index of the solvent. Single crystal X-ray diffraction studies Crystals of Me4B, Cl2B (A), (B), (C), and Me2B were mounted on a MiTeGen micromount with NVH immersion oil. Data were collected from a shock-cooled single crystal at 100(2) K on a Bruker Apex Kappa Duo
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Published 05 Mar 2025

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

  • Francesco Mele,
  • Ana M. Constantin,
  • Andrea Porcheddu,
  • Raimondo Maggi,
  • Giovanni Maestri,
  • Nicola Della Ca’ and
  • Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

Graphical Abstract
  • studied to get insights into the impact of light energy onto crystals [60][61]. In the following, we describe selected examples with an emphasis on the role of manual grinding in improving irradiation. Mechanochemistry is a linchpin in topochemical solid-state reactions, where the correct molecular
  • spectroscopy (Scheme 1). During the reaction progress, the C=C bonds of bpe ligands undergo pedal-like motion prior to photodimerization [63]. For the single-crystal irradiation, the slow reactivity can be attributed to the hindered pedal motion in the single crystals, likely due to the presence of
  • coordinative bonds on one side and hydrogen bonds on the other. Surprisingly, when the crystals were manually ground for 5 min before irradiation, the conversion to dimer 1.2 remarkably increased to 88% in only 4 h of UV irradiation time. Overall, the role of manual grinding was not only to increase the
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Published 03 Mar 2025

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

  • Yurii A. Sayapin,
  • Eugeny A. Gusakov,
  • Inna O. Tupaeva,
  • Alexander D. Dubonosov,
  • Igor V. Dorogan,
  • Valery V. Tkachev,
  • Anna S. Goncharova,
  • Gennady V. Shilov,
  • Natalia S. Kuznetsova,
  • Svetlana Y. Filippova,
  • Tatyana A. Krasnikova,
  • Yanis A. Boumber,
  • Alexey Y. Maksimov,
  • Sergey M. Aldoshin and
  • Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

Graphical Abstract
  • cell parameters and reflection intensities for compound 7b (a three-dimensional set) were measured on an Xcalibur EOS autodiffractometer (Mo Kα irradiation, graphite monochromator, 150 K). Orange monoclinic crystals, chemical formula C21H14NO2Cl3, М = 418.68, a = 11.4480(3), b = 7.4883(2), с = 21.7720
  • added and incubated for another 2 h under CO2 incubator conditions. At the end of cultivation, the medium with MTT was completely removed from the wells, and the formed formazan crystals were dissolved in DMSO and the optical density of the resulting solution was measured at 540 nm. The level of
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Published 17 Feb 2025

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

  • Kirill A. Gomonov,
  • Vasilii V. Pelipko,
  • Igor A. Litvinov,
  • Ilya A. Pilipenko,
  • Anna M. Stepanova,
  • Nikolai A. Lapatin,
  • Ruslan I. Baichurin and
  • Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

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  • phase and visualized under UV light (λ 254 nm). X-ray structure determination X-ray diffraction studies of single crystals of compounds 5a, 5b, 6b, 6c, and 7a were carried out on a Bruker D8 QUEST diffractometer. The cell parameters and experimental data were obtained at 100 K (graphite monochromator
  • , λMo Kα = 0.71073 Å, ω and φ scanning in 0.5° steps) at the distributed spectral-analytical center of shared facilities for study of structure, composition and properties of substances and materials of FRC Kazan scientific center of Russian academy of sciences. Crystals of compounds suitable for X-ray
  • structural analysis were obtained by crystallization from MeOH (5a), EtOH (5b), or DMFA (6b, 6c, and 7a). Single crystals of a suitable size were glued to the top of a glass fiber in a random orientation. The preliminary unit cell parameters were determined using three runs at different ω angle positions
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Published 12 Feb 2025

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

  • Islam S. Marae,
  • Jingyun Tan,
  • Rengo Yoshioka,
  • Zakaria Ziadi,
  • Eugene Khaskin,
  • Serhii Vasylevskyi,
  • Ryota Kabe,
  • Xiushang Xu and
  • Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

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  • and photonics [32][33][34][35]. However, precise preparation and shape control over organic crystals are still elusive targets [36]. We carried out SEM analysis of crystals of BPP-OiPr 3 obtained by slow evaporation of its solution in a mixture of dichloromethane and n-hexane (Figure 3). The formation
  • Supporting Information File 1), suggesting that the BPP core can lead to such rod-shaped crystals and nanowires. Conclusion In summary, we achieved a facile synthesis of BPP-OiPr 3 and studied its optical properties in comparison to pristine BPP 2 and its oxidation product BPP-dione 4. Both BPP-OiPr 3 and
  • variety in crystallization, including differences in shape, length, and width, b) rod-like crystals with lengths of hundreds of nanometers, c) rod-like crystals with lengths of hundreds of micrometers, and d) longer wire. Synthesis of BPP-OiPr 3 and BPP-dione 4. Reaction conditions for the synthesis of
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Published 04 Feb 2025

Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

  • Wentao Yu,
  • Zhiyao Yang,
  • Chengkan Yu,
  • Xiaowei Li and
  • Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

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  • ]. This is not only due to their rich host–guest chemistry but also due to π-surface-enabled self-assembly that enables the creation of various supramolecular structures, such as discotic liquid crystals [33], nanodimers [34], and organic frameworks [35]. Among them, shape-persistent hydrogen-bonded
  • the resonance of the internal aromatic protons Ha and Hb in the host H (Δδ= −0.170 and +0.218 ppm, respectively), which all pointed toward the existence of strong host–guest interactions in solution. Then we attempted to grow single crystals of the complex out of curiosity, wondering whether the 2:2
  • structure would also be found in the solid state. Fortunately, single crystals of the complex H1 ⊃ G1 were obtained by slow evaporation of chloroform/acetone solvent (1:1, v/v) into a small amount of methanol over the course of two weeks. Indeed, analysis of the crystal structure of the complex revealed a
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Published 17 Jan 2025

Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

  • Yongming Xiong,
  • Xue Lin Ma,
  • Shilong Su and
  • Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

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  • theoretical carbon structures known as carbon schwarzites or Mackay crystals. These names honor A. L. Mackay and H. A. Schwarz for their pioneering contributions. In 1991, Mackay introduced the idea of negatively curved carbon allotropes by incorporating octagons into the graphitic lattice [3]. Earlier, in
  • the 1880s, Schwarz described triply periodic minimal surfaces, which serve as the topological foundation for what are now known as Mackay crystals. Despite predictions that carbon schwarzites would have intriguing properties for various potential applications [4][5], they have not yet been
  • yellow crystals from the same solution. X-ray crystallography reveals that in the colorless crystal [27], compound 1 adopts a conformation with approximate Cs symmetry, with the plane of symmetry (σ) shown in the top view in Figure 2a. The structure of Cs-1 in this crystal is essentially the same as that
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Published 02 Jan 2025

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

  • Beatriz Dedeiras,
  • Catarina S. Caldeira,
  • José C. Cunha,
  • Clara S. B. Gomes and
  • M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

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  • benziodoxolone, 2d) were obtained with quantitative yields, as white solids on the gram-scale, easy to manipulate and long-term stable below 0 °C. Crystals of compound 2d were successfully obtained and its molecular structure was confirmed through single-crystal X-ray diffraction. The X-ray analysis revealed a
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Published 19 Dec 2024

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

  • Yang Chen,
  • Jiao He,
  • Hang Lin,
  • Hai-Feng Wang,
  • Ping Hu,
  • Bi-Qin Wang,
  • Ke-Qing Zhao and
  • Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

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  • -67034 Strasbourg, France 10.3762/bjoc.20.270 Abstract The high potential of non-covalent arene–fluoroarene intermolecular interactions in the design of liquid crystals lies in their ability to strongly promote self-assembly, improve the order and stability of the supramolecular mesophases, and enable
  • crystals (F-DLCs) [13][14][15][16][17] of interest for organic electronics and optical advanced materials, as they tend to promote more efficient molecular stacking into columns than their purely hydrogenated counterparts [18][19], thereby improving one-dimensional charge transport properties [20][21][22
  • ) was prepared to grow single crystals suitable for X-ray analysis (Scheme S2 in Supporting Information File 1) in order to confirm the annulation reaction pattern, and 2,3,6,7-tetrakishexyloxy-10-phenyltriphenylene (BTP6, Scheme S3), the non-fluorinated isomer of F6 and PH6 (Figure 1), for probing the
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Published 16 Dec 2024

Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF5- and CF3SF4-containing [2]staffanes

  • Jón Atiba Buldt,
  • Wang-Yeuk Kong,
  • Yannick Kraemer,
  • Masiel M. Belsuzarri,
  • Ansh Hiten Patel,
  • James C. Fettinger,
  • Dean J. Tantillo and
  • Cody Ross Pitts

Beilstein J. Org. Chem. 2024, 20, 3134–3143, doi:10.3762/bjoc.20.259

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  • for the first time created an opportunity for structural analysis. We previously reported and contextualized single-crystal X-ray diffraction (SC-XRD) data on 2 [36]; thus, we proceeded to grow crystals of 3 suitable for X-ray analysis through slow evaporation of ethyl acetate. To our surprise, an
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Published 29 Nov 2024

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

  • Anastasia I. Ershova,
  • Sergey V. Fedoseev,
  • Konstantin V. Lipin,
  • Mikhail Yu. Ievlev,
  • Oleg E. Nasakin and
  • Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

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  • the E-configuration. Spectral–luminescence properties Compounds 1 form colored crystals, from pale-yellow (i.e., 1a) to almost black (i.e., 1h). They are soluble and luminescent in most common organic solvents. Solvatochromism of stilbazole 1c, containing a para-methoxy group, was studied first (see
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Published 19 Nov 2024

Tailored charge-neutral self-assembled L2Zn2 container for taming oxalate

  • David Ocklenburg and
  • David Van Craen

Beilstein J. Org. Chem. 2024, 20, 3007–3015, doi:10.3762/bjoc.20.250

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  • of oxalate is an order of magnitude higher than the one of acetate and benzoate which is in line with the fact that oxalate is supposed to be pinched between both zinc centers while the monocarboxylates coordinate only to one zinc atom. Unfortunately, we could not grow suitable single crystals of
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Published 18 Nov 2024
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