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

• 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

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

• 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

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

• 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

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

• 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

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

• 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

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

• 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

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

• ]. 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

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

• 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

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

• 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

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

• -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

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

• 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

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

• 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

4,6-Diaryl-5,5-difluoro-1,3-dioxanes as chiral dopants for liquid crystal compositions

• Maurice Médebielle,
• Peer Kirsch,
• Jérémy Merad,
• Carolina von Essen,
• Clemens Kühn and
• Andreas Ruhl

Beilstein J. Org. Chem. 2024, 20, 2940–2945, doi:10.3762/bjoc.20.246

• dopants for liquid-crystal compositions. Keywords: chiral dopant; chirality; cholesteric phase; diols; fluorine; helical twisting power; liquid crystal; Introduction Liquid crystals for use in liquid crystal displays (LCDs) have become one of the most prominent application areas of fluoroorganic

• chemistry [1][2][3]. In particular, cholesteric, i.e., chiral nematic, liquid crystals (LCs) are attractive for many display applications due to their chiroptical characteristics as well as the selective reflection of light giving rise to Bragg interference colors [4]. Cholesteric LCs can be obtained either

• ) LCDs which need a higher HTP or increased dopant concentrations [8][9]. TN and STN displays are still based on liquid crystals in the nematic or cholesteric mesophase. Even higher concentrations of chiral dopants with extremely high HTP tend to induce a Blue Phase, which is a cubic mesophase composed

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• enhanced push–pull effect in this molecule due to the presence of a stronger acceptor. Furthermore, the energy of the LUMO of compound 3 is comparable to reported PDI-based acceptors which have been used in OPVs with PCE > 7% [34]. Crystallographic study Needle-shape crystals of compound 3b suitable for

Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction

• Yuta Kabumoto,
• Eiichiro Yoshimoto,
• Bing Xiaohuan,
• Masato Morita,
• Motohiro Yasui,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2776–2783, doi:10.3762/bjoc.20.233

•  1a, 1, 2) [10][11][12], liquid crystals (Figure 1b, 3, 4) [13][14][15][16][17], fluorescence materials (Figure 1c, 5) [18][19], and so on, have been developed in recent years. In sharp contrast to the major development of such non-chiral tetrafluoroethylenated compounds, there have been only few

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

• Connor R. M. MacDonald and
• Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

• material in its hydrated state. Cryogenic techniques utilise a vitrification process to maximise the formation of vitreous ice to minimise the formation of ice crystals which can disrupt the material structure. The ability of cryo-EM to probe the structure of soft nanostructured materials has led to a

• area-to-volume ratio which reduces the cooling rate reached in the vitrification process. High-pressure freezing (HPF) methods are capable of fixing samples 100 times thicker than plunge freezing. HPF reduces the growth of crystals during the fixation of cryo-SEM samples by using very high pressures of

Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

• Alfiya R. Gimadieva,
• Yuliya Z. Khazimullina,
• Aigiza A. Gilimkhanova and
• Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

• mixture to room temperature, concentrated H2SO4 was slowly added until pH 6–7 according to litmus paper and left standing for 12 h. The precipitated white crystals were filtered off, washed with water, and dried in air. Compound 2 yields are given in [13] and compound 5 yields are given in Table 1. b

• temperature, concentrated H2SO4 was slowly added until pH 6–7 according to litmus paper and left standing overnight (12 h). The precipitated crystals were filtered off, washed with water, acetone, and dried in air. The crude product was recrystallized from water with activated carbon. The yield of compound 2

• H2SO4 was added and the reaction mixture was stirred at the same temperature for 1 h and cooled. The precipitated crystals were filtered off, washed with cold distilled water to pH 6–7 (2 × 5 mL), and recrystallized from ethanol. 5-Hydroxy-6-methyluracil (3). Yield 98%. The spectral characteristics are

Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures

• Yohei Haketa,
• Takuma Matsuda and
• Hiromitsu Maeda

Beilstein J. Org. Chem. 2024, 20, 2567–2576, doi:10.3762/bjoc.20.215

• orthogonal arrangement in comparison with the phenyl moieties in 1b+. Solid-state ion-pairing assemblies of the ion pairs 2+-X− (X− = Cl−, BF4−, PF6−, B(C6F5)4−, and PCCp−) were investigated by X-ray analysis of the orange rod-shaped single crystals, which were obtained by vapour diffusion using CHCl3/n

• -heptane for 2+-Cl−, 2+-BF4−, and 2+-PCCp−, CH2Cl2/n-heptane with small amounts of MeOH and toluene for 2+-PF6−, and toluene/n-hexane for 2+-B(C6F5)4− (Figure 3 and Figures S11–15 in Supporting Information File 1) [32]. In the single crystals, 2+ showed highly planar core structures with mean-plane

HFIP as a versatile solvent in resorcin[n]arene synthesis

• Hormoz Khosravi,
• Valeria Stevens and
• Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

• , chlorinated species 1h and 1i, and carboxylic acid-containing 1s, developed high quality crystals from standing solutions in dimethyl sulfoxide for 1h and 1i, and methanol for 1s. Their molecular crystal structures were determined and are shown in Figure 1b displaying the classic cone conformation for both

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• ), HRMS, and elemental analysis. The molecular structures of compounds 5, 6 and 8 in crystal state were determined by single-crystal X-ray analysis. X-ray data The X-ray suitable crystals 5, 6·0.5CH3CN, and 8 were grown by slow recrystallization of the compounds from acetonitrile solutions. The unit cells

• of complexes 5 and 8 do not contain any solvent molecules, while the unit cell of crystals 6·0.5CH3CN contains one acetonitrile molecule per two catechol molecules. The nitro-substituted pyridine group in 5 is disordered in two positions. The X-ray structure of catechol 5 is shown in Figure 1, and

• of neighboring molecules [57][58][59][60][61]. The intra- and intermolecular interactions in crystals 5, 6·0.5CH3CN, and 8 lead to different complex structural motifs in crystals of these compounds. Two intramolecular hydrogen bonds (Figure 1) are observed in the crystal structure of 5: between OH

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• ][12][13]. The most promising applications of truxene-based systems have been found in organic photovoltaics (OPVs), dye‐sensitized solar cells (DSSCs), fluorescent probes, organic thin‐film transistors (OTFTs), lasers, organic light emitting diodes (OLEDs), liquid crystals, non-linear optical (NLO

Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies

• Beatrice E. Jones,
• Camille Blayo,
• Jake L. Greenfield,
• Matthew J. Fuchter,
• Nathan Cowieson and
• Rachel C. Evans

Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176

• Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany 10.3762/bjoc.20.176 Abstract Dynamic, responsive materials can be built using photosurfactants (PS) that self-assemble into ordered nanostructures, such as micelles or liquid crystals. These PS contain photoswitchable groups, such as

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• Alexander V. Tsygankov Vladyslav O. Vereshchak Tetiana O. Savluk Serhiy M. Desenko Valeriia V. Ananieva Oleksandr V. Buravov Yana I. Sakhno Svitlana V. Shishkina Valentyn A. Chebanov Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of

Synthesis and characterization of 1,2,3,4-naphthalene and anthracene diimides

• Adam D. Bass,
• Daniela Castellanos,
• Xavier A. Calicdan and
• Dennis D. Cao

Beilstein J. Org. Chem. 2024, 20, 1767–1772, doi:10.3762/bjoc.20.155

• . Crystallography Despite exhaustive efforts, we were unable to obtain single crystals of 7-Hex and 8-Hex; these compounds formed polycrystalline bundles that are fragile and insufficient for obtaining diffraction data. Fortunately, single crystals of the N-phenyl compounds were successfully grown by slow