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Search for "solid state" in Full Text gives 456 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

  • Recep Isci and
  • Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

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  • absorption and emission maxima of 411 and 520 nm, respectively, with a mega Stokes shift of 109 nm and fluorescence quantum yields both in the solid state (41%) and in solution (86%). The optical properties were supported by computational chemistry using density functional theory for optimized geometry and
  • emitter for an organic light-emitting diode through a solution process. DMB-TT-TPA (8) displayed excellent performance in both device application and photophysical properties, i.e., a maximum solution fluorescence quantum yield of 86% in THF, maximum solid-state fluorescence quantum yield of 41%, maximum
  • ]thiophene (TT) core. The optical band gap (Eoptic) of DMB-TT-TPA (8) was calculated to be 2.52 eV from the onset wavelength of the absorption spectrum at 491 nm. The compound demonstrates high quantum efficiencies in the solid-state and in solution (THF) of 41 and 86%, respectively. The considerable quantum
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Published 07 Dec 2023

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

  • Dayanne Martins,
  • Roberta Lamosa,
  • Talis Uelisson da Silva,
  • Carolina B. P. Ligiero,
  • Sérgio de Paula Machado,
  • Daphne S. Cukierman and
  • Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

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  • -acylhydrazones were synthesized and fully characterized, both in solution and in the solid state. The compounds differ with respect to the carbonyl precursors, i.e., 3-substituted salicylaldehydes with either a methyl or a nitro group. Single crystals of both compounds were isolated from the respective mother
  • phenolic hydroxy group and the azomethine nitrogen was identified in the solid state and seems to be maintained in solution. Moreover, the presence of the electron-withdrawing nitro substituent makes this interaction stronger. However, the contact should probably not subsist for the nitro compound under
  • hydrazone, it is evident that deprotonation is almost complete at pH 7.4. For this reason, the intramolecular H-bond identified both in the solid state (XRD, IR) and in solution (1H NMR) is probably absent under physiological or pseudo-physiological conditions. Although still stable at pH 7.4, the hdz-NO2
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Published 10 Nov 2023

Quinoxaline derivatives as attractive electron-transporting materials

  • Zeeshan Abid,
  • Liaqat Ali,
  • Sughra Gulzar,
  • Faiza Wahad,
  • Raja Shahid Ashraf and
  • Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

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  • emissive nanoaggregates in a THF/H2O mixture. Altering the substituents proved as an effective approach to tune the electrochemical properties of the compounds, resulting in comparable LUMO energy levels. The products therefore hold potential as solid-state emitters and n-type materials for organic
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Published 09 Nov 2023

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

  • Swagat K. Mohapatra,
  • Khaled Al Kurdi,
  • Samik Jhulki,
  • Georgii Bogdanov,
  • John Bacsa,
  • Maxwell Conte,
  • Tatiana V. Timofeeva,
  • Seth R. Marder and
  • Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

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  • only introduced in n-dopants in 2010, when Bao and co-workers reported the use of N-DMBI-H (1bH, Figure 1) to n-dope fullerenes [7]. Although widely used, due to their facile synthesis, structural tunability, and good air stability in the solid state, 1H derivatives are relatively limited in dopant
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Published 01 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

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  • anion. The formed receptor: ion-pair 1:1 complex 4-CsF was stable in solution, as evidenced by 1H NMR spectroscopy. The binding constant Ka = 3.8·105 M−1 in CHCl3/MeOH 9:1 was reported. The XRD analysis in the solid state provided further proof of the binding mode, demonstrating the significant
  • ]. The CsF binding led to a supramolecular self-assembly process, inducing a sandwich host–guest complex formation in the solid state (Scheme 2). It was established that fluoride is preferred over any other halide anions. The binding of the ion pairs was observed in highly polar solvent media, but in the
  • , emphasising the structural motif's ability to stabilise guest molecules through primary and secondary sphere bonding interactions. Compound 19-Cr, similarly to 18a-Ti and 18a-V, also exhibited paramagnetic features. The solid state structure demonstrated the complex featuring a Cr3+ cation bound in a
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Published 27 Oct 2023

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

  • Nosheen Beig,
  • Varsha Goyal and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

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  • -Ph) in this manner (Scheme 29) [42]. The X-ray studies revealed two major structure types of the compounds [(NHC)Cu-ER3] in the solid state. In the case of bulky NHC ligands, such as IDipp, IMes, and It-Bu, the CuI complexes with ER3 = SiMe2Ph, SiPh3, SnMe3 as well as for Ph and CC-Ph, have monomeric
  • NEt3·3HF, AgHF2 could also be used. The complexes were found to be air-stable in the solid state and moderately stable in solution. They were unambiguously characterized on the basis of NMR studies including 19F NMR and X-ray crystal analysis. With the IMes ligand, an air-stable bis(NHC)Cu(I) complex
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Published 20 Sep 2023

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

  • Nadia Ledermann,
  • Alae-Eddine Moubsit and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

Graphical Abstract
  • absorption maximum of indole derivative 8b appears at 309 nm with an absorption coefficient ε = 10700 M−1 cm−1 and the emission maximum is found at 423 nm with a Stokes shift of 8700 cm−1 (Figure 1A). Moreover, compound 8b emits intensively blue in both the solid state and solution (Figure 1B). Conclusion In
  • interest as indole-based blue emitters in solution and in the solid state. The expansion of this practical concise synthesis of indoles and azaindoles and their exploration as biologically active apoptosis inducers [37] and as functional blue emitters is currently underway. Experimental Consecutive four
  • , 6.29; N, 4.52. A: Absorption and emission spectra of 1-methyl-2-phenyl-3-(p-tolyl)-1H-indole (8b), recorded in dichloromethane, T = 298 K, λexc = 290 nm. B: Emission of compound 8b in the solid state (right) and in solution (left) (UV lamp, λexc = 365 nm. Consecutive alkynylation–cyclization–alkylation
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Published 14 Sep 2023

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

  • Winnie Chemutai Sum,
  • Sherif S. Ebada,
  • Didsanutda Gonkhom,
  • Cony Decock,
  • Rémy Bertrand Teponno,
  • Josphat Clement Matasyoh and
  • Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

Graphical Abstract
  • Chemical exploration of solid-state cultures of the polypore Fomitopsis carnea afforded two new C31 lanostane-type triterpenoid glycosides, forpiniosides B (1) and C (2) together with two known derivatives, namely 3-epipachymic acid (3) and (3α,25S)-3-O-malonyl-23-oxolanost-8,24(31)-dien-26-oic acid (4
  • solid-state cultivated cultures of F. carnea, with forpinioside B (1) proving to be a potential antimicrobial. In addition, our findings provide significant insights to decipher the SARs of the lanostanoid triterpenoids. Experimental General experimental methods The samples were analyzed on an amaZon
  • comparison of its morphological traits to close relatives. Fermentation and metabolites extraction Mycelial cultures of F. carnea were fermented on solid and liquid-state media based on previously established methodologies [37]. Essentially, the preparation of solid-state media was as follows: 90 mg of rice
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Published 02 Aug 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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Published 28 Jul 2023

Light-responsive rotaxane-based materials: inducing motion in the solid state

  • Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

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  • Adrian Saura-Sanmartin Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, 30100 Murcia, Spain 10.3762/bjoc.19.64 Abstract Light-responsive rotaxane-based solid-state materials are ideal scaffolds in order to develop smart materials due to the properties provided by the
  • is the functionalization of mesoporous silica nanoparticles with light-responsive rotaxane-based molecular shuttles to control the uptake and release of target molecules [31][32][33][34]. This perspective is focused on recent examples of light-responsive rotaxane-based solid-state materials in which
  • analyze selected recent examples, a critical opinion on the state of the art is provided, including some future directions of this research field and postulating light-responsive solid-state rotaxane materials as tailorable scaffolds which will be used in a wide range of advanced applications. Discussion
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Published 14 Jun 2023

Construction of hexabenzocoronene-based chiral nanographenes

  • Ranran Li,
  • Di Wang,
  • Shengtao Li and
  • Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

Graphical Abstract
  • of 91 was significantly improved. The enantiomers of 91 were proved as NIR-CPL emitters with 600 to 800 nm range of emission and glum values of 3 × 10−3 both in solution and in the solid state. Multilayer (e.g., bilayer and trilayer) graphenes that are composed of stacked graphenic layers exhibit
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Published 30 May 2023

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

  • Nan Yang,
  • Yi-Yan Zhu,
  • Wei-Xiu Lin,
  • Yi-Long Lu and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

Graphical Abstract
  • reaction to generate the corresponding multiple Schiff bases and then reduced with sodium borohydride (Scheme 1a). The structure of CS-TPE was characterized by 1H NMR spectra and solid-state CP/MAS 13C NMR spectra, and the results were found to agree with the proposed structure. For instance, the products
  • 20 mol % was calculated to be 1.6, 3.2 and 6.6 mol %, respectively, increasing as Rf increased. Fluorescent properties of CS-TPE in the solid state. CS-TPE bioconjugates were found to be AIE active, like other TPE-modified derivatives in previous works [25][26]. As shown in Figure 2a, the solid
  • illumination in the solid state due to powerful self-quenching effects in the aggregates [25]. Strong emission is observed at approximately 485 nm for all CS-TPE bioconjugates in the solid state (Figure 2b). A major reason for the emission behavior is the restriction in intramolecular rotation (RIR) of
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Published 08 May 2023

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

  • Josipa Matić,
  • Tana Tandarić,
  • Marijana Radić Stojković,
  • Filip Šupljika,
  • Zrinka Karačić,
  • Ana Tomašić Paić,
  • Lucija Horvat,
  • Robert Vianello and
  • Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

Graphical Abstract
  • applications [9]. These compounds have a very large aromatic surface suitable to form self-assembled supramolecular structures by intermolecular π–π interactions and showed excimer fluorescence in thin film and in the solid state. Kawai et al. reported exciplex formation between pyrene and guanine in polar
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Published 26 Apr 2023

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K3PO4

  • Ina Remy-Speckmann,
  • Birte M. Zimmermann,
  • Mahadeb Gorai,
  • Martin Lerch and
  • Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

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  • complexes: Synthesis of bifunctional catalyst 5 via transmetallation. Mes = mesityl [48][49]. Application of bifunctional catalyst 5 in copper(I)-catalyzed hydrogenations: comparison of 5 prepared by solid state/ball milling (5bm) and liquid state (5ls) synthesis. Standard conditions: Substrate (0.40 mmol
  • ), 10 mol % 5, 1.1 equiv NaOt-Bu, 1.3 equiv 15-crown-5, 100 bar H2, 1,4-dioxane (3 mL), 70 °C, 24 h. Attempted direct synthesis of bifunctional catalyst 5 from imidazolinium salt 3: liquid and solid state approaches. Synthesis of standard Cu(I)/NHC-complexes using K3PO4 as a weak base (standard
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Published 14 Apr 2023

Preparation of β-cyclodextrin/polysaccharide foams using saponin

  • Max Petitjean and
  • José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

Graphical Abstract
  • , certainly because of a higher homogenization of the pre-crosslinked matrix. When prepared in powder (solid-state) form (45spPow), adding saponin will decrease the percent yield from 70% to 50%. Interestingly, the yield is not affected in that way when adding saponin into the liquid mixture (45spLiq
  • or in the solid state, as shown in Figure 8. Thus, the solid mixtures were homogenized using a mortar as in previous works [38][39], and crosslinked at 170 °C during 20 or 45 min (samples 20Pow and 45Pow). A solid-state mixture with the addition of 0.5 g of saponin and a thermal crosslinking at 170
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Published 24 Jan 2023

Improving the accuracy of 31P NMR chemical shift calculations by use of scaling methods

  • William H. Hersh and
  • Tsz-Yeung Chan

Beilstein J. Org. Chem. 2023, 19, 36–56, doi:10.3762/bjoc.19.4

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  • compounds when using the M06-2X optimization and the M06-L/GIAO NMR calculation (Table 4, entry 14). Interestingly, this functional was not recommended in a recent study on calculation of solid-state chemical shifts for 31P NMR [103]. Use of the CSGT NMR method gave a higher MAD (Table 4, entry 15) and M06
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Published 10 Jan 2023

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

  • Alexios I. Vicatos,
  • Zakiena Hoossen and
  • Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

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  • , which is a distinct disadvantage for solid-state structural investigation and complex characterization by X-ray diffraction methods. Results and Discussion Complex screening The isolation of solid inclusion complexes of BES and PRO with the native cyclodextrins β-CD and γ-CD was successfully achieved by
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Published 22 Dec 2022

Inline purification in continuous flow synthesis – opportunities and challenges

  • Jorge García-Lacuna and
  • Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

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  • purification via a catch and release strategy [96]. Additionally, functionalized residues can be used to perform a solid-state synthesis approach, such as in the synthesis of 2-aminopyridine derivatives starting from amino-iminium residues [97]. To improve on this technology, Baxendale and co-workers utilized
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Published 16 Dec 2022

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

  • Ruslan P. Shekurov,
  • Mikhail N. Khrizanforov,
  • Ilya A. Bezkishko,
  • Tatiana P. Gerasimova,
  • Almaz A. Zagidullin,
  • Daut R. Islamov and
  • Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

Graphical Abstract
  • °, respectively, has been observed, although a propeller-like gauche-gauche-gauche configuration of alkyl(aryl)thio groups has been observed for trithiophosphites even in the solid state [7] or in the gas phase [8][9][10]. Triferrocenyl trithiophosphite has nine axes of internal rotation: three P–S bonds, three C
  • ···π-bonded dimers (Figures S4 and S5 in Supporting Information File 1). The computations of the relative energies of five possible conformers of (PhS)3P (ggg, ttt, ttg, ggt, ccg) predict the lowest energy for the ccg conformation (Figure 5). The propeller-like ggg conformer found in the solid state
  • optimized ttg conformer (left) and for two neighboring molecules (right) from X-ray analysis data. Molecular structures in the solid state of a) (FcS)3P, b) (FcS)3PO [19], and c) (FcS)3PS [7] as established by single crystal X-ray diffraction analyses. C atoms – grey, Fe atoms – brown, O atoms – red, P
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Published 25 Oct 2022

Dissecting Mechanochemistry III

  • Lars Borchardt and
  • José G. Hernández

Beilstein J. Org. Chem. 2022, 18, 1454–1456, doi:10.3762/bjoc.18.150

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  • halides as substrates in multiple reactions. For instance, within this Thematic Issue, the synthetic relevance of aryl halides was evidenced during the development of a protocol for the solid-state palladium-catalyzed borylation reported by Kubota, Ito, and co-workers (Scheme 2) [6]. Moreover, Štrbac and
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Published 12 Oct 2022

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

  • Sanaz Ahmadipour,
  • Alice J. C. Wahart,
  • Jonathan P. Dolan,
  • Laura Beswick,
  • Chris S. Hawes,
  • Robert A. Field and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

Graphical Abstract
  • minimum volume of hot EtOH, enabling solid state analysis (Figure 2). Crystals of 16 were analysed by single crystal X-ray diffraction and the data were solved in the monoclinic space group P21. Although the crystals suffered from intrinsic non-merohedral twinning through a non-crystallographic rotation
  • , the structural model allowed unambiguous assignment of the solid state molecular structure and absolute configuration. As shown in Figure 2, the desired axial anomeric phosphate was clearly visible alongside an interesting gg rotameric form for the C6–chloro side chain substituent (pyranose side chain
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Published 30 Sep 2022

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

  • Attila Palágyi,
  • Jindřich Jindřich,
  • Juraj Dian and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

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  • benzaldehyde) and static headspace-gas chromatography (for benzaldehyde, heptanal, and 5-methylfurfural). The aldehyde release rate from the imine was shown to depend substantially on the pH from the solution and the air humidity from the solid state. Keywords: aldehyde; controlled release; cyclodextrin
  • the release of flavor in solution or solid state [29][30][31]. The aldehyde release was studied using three different sampling time intervals corresponding to three time regions I, II, and III, in Figures 5–7. This experiment mode enabled better observation of the trends in the change of the aldehyde
  • the system. Sustained release of the aldehyde was demonstrated both in aqueous solutions and from a solid state upon humidity exposure. Experimental Instruments, general methods, and chemicals 1H NMR, 13C NMR, 2D NMR (H,H-COSY, HSQC, and HMBC) were measured on Bruker AVANCE III 600 MHz (600.17 MHz for
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Published 28 Sep 2022

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

  • Merve Karaman,
  • Abhishek Kumar Gupta,
  • Subeesh Madayanad Suresh,
  • Tomas Matulaitis,
  • Lorenzo Mardegan,
  • Daniel Tordera,
  • Henk J. Bolink,
  • Sen Wu,
  • Stuart Warriner,
  • Ifor D. Samuel and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

Graphical Abstract
  • suggests that the conformation of the emitter in the solid state is slightly more conjugated than that in solution or that there are specific host–guest interactions with the DPA unit that perturbs the energy of the excited state. The emission is broader than that of a structurally similar emitter, QAD
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Published 22 Sep 2022

Polymer and small molecule mechanochemistry: closer than ever

  • José G. Hernández

Beilstein J. Org. Chem. 2022, 18, 1225–1235, doi:10.3762/bjoc.18.128

Graphical Abstract
  • solution and when ball milled in the solid state [29]. The results for bottlebrush polymers demonstrated a more pronounced arm scission by ball milling than by sonication, compared to the extent of backbone rupture. However, for dendronized polymers, arm scission could be accomplished by ball milling but
  • between ball milling and ultrasonication were associated with the more restricted chain mobility in the solid state and with the dissimilar distribution of mechanical forces on the backbone and arms. With ball milling, these were more pronounced towards the arms of the polymer [29]. Other studies have
  • to generate radicals (Scheme 3) [67]. The difference in the C–C bond scission between 6 and 8 was explained based on the ability of diarylurea moieties in 8 to form strong self-assemblies through hydrogen bonding. In the solid state, this enabled the transduction of mechanical force to the
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Published 14 Sep 2022

From amines to (form)amides: a simple and successful mechanochemical approach

  • Federico Casti,
  • Rita Mocci and
  • Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126

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  • ]. In general, mechanochemistry refers to studying solid-state chemical changes promoted by external mechanical energy, such as grinding or milling. A deeper understanding of its mechanistic aspects laid the basis for further growth in this topic, opening new routes to more efficient mechanochemical
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Published 12 Sep 2022
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