Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• be enhanced by ternary complexation. Results and Discussion Synthesis and thermal analysis of the ternary complexes The complexity of the starting materials, especially that of hazelnut oil, as well as the differences among their characteristics (hydrophobicity and water solubility) suggest the

• complexes is much higher (e.g., 11.8% for X3N complex). As a consequence, the 1:1:1 complexes lose relatively more hydration water than the corresponding 3:1:1 complexes. This can be explained by the high level of complexation for the 1:1:1 complexes. This aspect could be confirmed by thermal analysis

• thermal/oxidative stability of ternary complexes is similar to β-CD hydrate, as was evaluated by TG and DSC. Moreover, the formation of the molecular inclusion complexes is supported by thermal analysis (partial replacing of the hydration water by biologically active molecules and disappearance of the DSC

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• from 25 °C to 900 °C with a 10 K/min heating rate and the mass loss measured. The resulting data were evaluated with the NETZSCH Proteus – Thermal Analysis – V.5.2.1 software. Dynamic scanning calorimetry (DSC) was performed on a DSC 204F1 Phoenix (NETZSCH, Selb, Germany) under a N2 atmosphere (20.0 mL

• /min). Samples were placed in aluminum pans, heated up to 200 °C and then cooled to −50 °C (10 K/min). The heating/cooling was repeated two additional times. The resulting thermograms were analyzed with the NETZSCH Proteus – Thermal Analysis – V.5.2.1 software. The polymerization of 2-alkyl-2

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

• via co-precipitation. The results for the host–guest ratios were as follows: β-CD·BES (2:1), β-CD·PRO (2:1), γ-CD·BES (1:1), γ-CD·PRO (3:2). Fully assigned spectral analyses are also available (Figures S3–S8 and Tables S1–S4 in Supporting Information File 1). Thermal analysis The highly reproducible

• performed on a Bruker Ultrashield 400 Plus Spectrometer (Billerica, Massachusetts, U.S.A.) and the program MestReNova was used to analyse the resulting data [48]. Thermal analysis Hot stage microscopy (HSM): The crystals were immersed in a small amount of silicone oil and heated at a constant rate of 10

Water inside β-cyclodextrin cavity: amount, stability and mechanism of binding

• Stiliyana Pereva,
• Valya Nikolova,
• Silvia Angelova,
• Tony Spassov and
• Todor Dudev

Beilstein J. Org. Chem. 2019, 15, 1592–1600, doi:10.3762/bjoc.15.163

• differential thermal analysis with thermogravimetry (DTA/TG) and by differential scanning calorimetry (DSC) using a Perkin-Elmer DSC-7. The samples were heated from room temperature (25 °C) to 200 °C with different constant scanning rates – from 2 to 10 K min−1 in pure nitrogen atmosphere. Temperature and heat

Synthesis of polydicyclopentadiene using the Cp₂TiCl₂/Et₂AlCl catalytic system and thin-layer oxidation of the polymer in air

• Zhargolma B. Bazarova,
• Ludmila S. Soroka,
• Alex A. Lyapkov,
• Мekhman S. Yusubov and
• Francis Verpoort

Beilstein J. Org. Chem. 2019, 15, 733–745, doi:10.3762/bjoc.15.69

• -permeation chromatography on the instrument Agilent Technologies 1260 Infinity with a refractive index detector, GPC/SEC – styrogel column, length 300 mm, internal diameter 7.5 mm, eluent (CHCl3) rate 1 mL/s, calibration according to the polystyrene standards known molecular weight. Thermal analysis was

Selective formation of a zwitterion adduct and bicarbonate salt in the efficient CO₂ fixation by N-benzyl cyclic guanidine under dry and wet conditions

• Yoshiaki Yoshida,
• Naoto Aoyagi and
• Takeshi Endo

Beilstein J. Org. Chem. 2018, 14, 2204–2211, doi:10.3762/bjoc.14.194

• . Especially, the results of the thermal analysis revealed that the obtained zwitterion adduct and bicarbonate salt stabilized the dimer complexes based on multiple intermolecular hydrogen bonds. This also indicated that the zwitterion adduct, bicarbonate salt, and their dimers were a fairly stable structure

Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases

• Svetlana O. Kasatkina,
• Ekaterina E. Stepanova,
• Maksim V. Dmitriev,
• Ivan G. Mokrushin and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2018, 14, 1734–1742, doi:10.3762/bjoc.14.147

• simultaneous thermal analysis (STA, Table 1). According to the data obtained, PQTs 1a–h underwent thermal decomposition with a mass loss accompanied by an endothermic effect and CO evolution (Figure 4). The values of the mass loss corresponded to the elimination of a CO molecule from a PQT. Having taken into

• account the results of the thermal analysis, we examined the feasibility and conditions of the intermolecular reaction of the ketene generated from PQT 1a with benzalaniline (2a). The reaction mixtures obtained were investigated by UPLC–MS and the results are summarized in Table 2. The reaction mixtures

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• using elemental analysis, powder X-ray diffraction (PXRD), Raman, infrared and 13C{1H} CP-MAS NMR spectroscopies, and thermal analysis (TGA) to verify fisetin inclusion and to present a hypothetical structural arrangement for the host–guest units. The antioxidant activity of the γ-CD·fisetin inclusion

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• rich and more complicated phase space than indicated by simple thermal analysis. For BQR, variable temperature UV–vis spectroscopy mapped the transmitted light variations that accompany the phase change noted in the POM studies of BQR. We are currently studying the structural changes occurring in thin

Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin

• Daniel I. Hădărugă,
• Mustafa Ünlüsayin,
• Alexandra T. Gruia,
• Cristina Birău (Mitroi),
• Gerlinde Rusu and
• Nicoleta G. Hădărugă

Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20

• reduced after complexation and the ratio between the volumes of the titrant corresponding to “surface” and “strongly-retained” water can furnish further information on the molecular encapsulation efficiency (further studies are needed). Thermal analysis – KFT correlations Thermal analysis methods such as

• 10.0 °C·min−1 were used. The analysis was performed under nitrogen. The acquisition and handling of the data from the thermogravimeter were performed by using Netzsch Proteus – Thermal Analysis version 6.1 software. DSC analysis of β-CD/ASO complexes Calorimetric effects during heating of the β-CD/ASO

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• (2ME) and a series of cyclodextrins (CDs) was investigated in the solid state using thermal analysis and X-ray diffraction, while the possibility of enhancing its poor aqueous solubility with CDs was probed by means of equilibrium solubility and dissolution rate measurements. Single crystal X-ray

• investigated to gain insight into CD–steroid interaction modes and the stability of the resulting inclusion complexes. These researchers also used Fourier transform infrared spectroscopy (FTIR), thermal analysis and powder X-ray diffraction (PXRD) to infer the existence of solid native CD–steroid inclusion

• employed for preliminary investigation of single crystals of a putative inclusion complex between 2ME and DIMEB, prepared using the co-precipitation method. (Details of the thermal analysis of the DIMEB complex of 2ME are provided in the Supporting Information File 1). The crystals, immersed in silicone

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

• Jing Lin,
• Tao Kong,
• Lin Ye,
• Ai-ying Zhang and
• Zeng-guo Feng

Beilstein J. Org. Chem. 2015, 11, 2267–2277, doi:10.3762/bjoc.11.247

• chemical bond [22]. This confirmed that the PMPC segments were successfully attached to two ends of the pentablock polymer to convert γ-CD/PMA-PPO-PEO-PPO-PMA PPRs into the PR-based multiblock copolymers [14][23]. Thermal analysis TGA analysis was carried out to further confirm the structure of the PPRs

Consequences of the electronic tuning of latent ruthenium-based olefin metathesis catalysts on their reactivity

• Karolina Żukowska,
• Eva Pump,
• Aleksandra E. Pazio,
• Krzysztof Woźniak,
• Luigi Cavallo and
• Christian Slugovc

Beilstein J. Org. Chem. 2015, 11, 1458–1468, doi:10.3762/bjoc.11.158

• initiation efficacy is above all determined by the position of the trans–cis equilibrium which can be quickly reached at 110 °C [29][55]. In the second step, the initiators were tested in neat monomer using simultaneous thermal analysis (STA) for monitoring the polymerizations. As the monomer, either endo

Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths

• Yuchun Ren,
• Bin Wang and
• Xiuqing Zhang

Beilstein J. Org. Chem. 2015, 11, 1089–1095, doi:10.3762/bjoc.11.122

• spectra were recorded using a spectrophotometer (UV-3600, Shimadzu, Japan). Differential scanning calorimetry (DSC) was carried out on a thermal analysis (TA) DSC-Q30 in nitrogen at a heating rate of 10 K/min. Synthetic procedures Synthesis of m2–m12. 3β-[(2-hydroxyethyl)oxy]cholest-5-ene (m2) was

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• three crystalline inclusion complexes were also fully characterized by thermal analysis (hot stage microscopy, thermogravimetric analysis and differential scanning calorimetry). To complement the solid-state data, phase-solubility studies were conducted using a series of CDs (native and variously

• derivatised) to establish their effect on the aqueous solubility of trans-resveratrol and to estimate association constants for complex formation. Keywords: cyclodextrin; inclusion complexes; thermal analysis; trans-resveratrol; X-ray structures; Introduction The naturally occurring phytoalexin trans

• , although cellulose acetate was not tested in the present study. Conclusion A variety of methods (physical mixing, kneading, microwave irradiation) of effecting interaction between RSV and three CD hosts (TMA, DMB and TMB) was tested and a combination of thermal analysis and FTIR spectroscopy subsequently

Modification of physical properties of poly(L-lactic acid) by addition of methyl-β-cyclodextrin

• Toshiyuki Suzuki,
• Ayaka Ei,
• Yoshihisa Takada,
• Hiroki Uehara,
• Takeshi Yamanobe and
• Keiko Takahashi

Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

• plastics. In this study, the effect of methylcyclodextrin (MeCD) addition on the structure and physical properties, especially the drawing behavior, of PLLA was investigated. Through thermal analysis, it was found that MeCD addition lowers the crystallinity and enhances the mobility of PLLA. The sample

• abbreviated name (e.g., PL-MCD50 for MeCD/PLLA = 1:1). The obtained films were used for the experiments; for MeCD, the as received powder was used. Thermogravimetry/differential thermal analysis (TG-DTA) TG-DTA (Perkin-Elmer STA6000) was carried out at 10 °C min−1 under a nitrogen flow of 60 mL min−1 with 5

Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

• Daniel I. Hădărugă,
• Nicoleta G. Hădărugă,
• Corina I. Costescu,
• Ioan David and
• Alexandra T. Gruia

Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

• formation was determined by thermal analysis (TG, DSC), FTIR and XRD. The quality of the encapsulation has been studied by gas chromatographic methods. Methylchavicol and other structurally related volatiles were also encapsulated in various natural CDs such as α- and β-CD, as well as in semisynthetic

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

• Clara Orofino-Pena,
• Diego Cortizo-Lacalle,
• Joseph Cameron,
• Muhammad T. Sajjad,
• Pavlos P. Manousiadis,
• Neil J. Findlay,
• Alexander L. Kanibolotsky,
• Dimali Amarasinghe,
• Peter J. Skabara,
• Tell Tuttle,
• Graham A. Turnbull and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

• . Supporting Information Supporting Information File 398: Experimental procedures for all new compounds, thermal analysis, cyclic voltammograms and associated data, photophysical data, computational data, 1H NMR spectra for all new compounds. Acknowledgements The authors wish to thank the EPSRC for funding

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• isotherms and in the solid state by thermal analysis (DSC) and X-ray diffractometry. The variation of the alkyl chain structure of the p-hydroxybenzoic acid esters revealed that the stability of the inclusion complexes was deeply modified (see binding constants in Table 3). As depicted in Table 3, the

Copolymerization and terpolymerization of carbon dioxide/propylene oxide/phthalic anhydride using a (salen)Co(III) complex tethering four quaternary ammonium salts

• Jong Yeob Jeon,
• Seong Chan Eo,
• Jobi Kodiyan Varghese and
• Bun Yeoul Lee

Beilstein J. Org. Chem. 2014, 10, 1787–1795, doi:10.3762/bjoc.10.187

• using a Waters Millennium apparatus with polystyrene standards. The Tg data were determined from a second heating at a heating rate of 10 °C/min by differential scanning calorimetry (DSC) using a Thermal Analysis Q10 instrument. Typical procedure for PO/PA alternating copolymerizations. A bomb reactor

Aryl substitution of pentacenes

• Andreas R. Waterloo,
• Anna-Chiara Sale,
• Dan Lehnherr,
• Frank Hampel and
• Rik R. Tykwinski

Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178

• (vide infra). Thermal analysis The thermal stability of selected aryl pentacenes has been explored by traditional melting point analysis (MPA) in open capillary tubes, thermal gravimetric analysis (TGA), and differential scanning calorimetry (DSC) measurements; the results are summarized in Table 2. TGA

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

• Dyanne L. Cruickshank,
• Natalia M. Rougier,
• Raquel V. Vico,
• Susan A. Bourne,
• Elba I. Buján,
• Mino R. Caira and
• Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

• . Results and Discussion Thermal analysis Figure 2 shows representative thermogravimetric (TGA) and differential scanning calorimetric (DSC) traces for the novel inclusion complex DIMEB·1. Three reproducible thermal events occur in the DSC trace, the first of which is a small endotherm at 132 °C, which we

• guest from the inclusion complex resulted in an estimated 17.9 ± 0.3% (n = 2) mass loss, which is in good agreement with the theoretical value of 17.2% for a 1:1 host–guest complex. The complex stoichiometry deduced from thermal analysis was subsequently confirmed by NMR spectroscopy, as described below

• Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; email: deposit@ccdc.cam.ac.uk]. Thermal analysis Mass loss on heating the crystals of DIMEB·1 was measured on a TA-Q500 Thermogravimetric Analyzer, TA instruments, equipped with Universal Analysis 2000 software. The

Self-assembled organic–inorganic magnetic hybrid adsorbent ferrite based on cyclodextrin nanoparticles

• Ângelo M. L. Denadai,
• Frederico B. De Sousa,
• Joel J. Passos,
• Fernando C. Guatimosim,
• Kirla D. Barbosa,
• Ana E. Burgos,
• Fernando Castro de Oliveira,
• Jeann C. da Silva,
• Bernardo R. A. Neves,
• Nelcy D. S. Mohallem and
• Rubén D. Sinisterra

Beilstein J. Org. Chem. 2012, 8, 1867–1876, doi:10.3762/bjoc.8.215

• thermal analysis (TG/DTA), and by their magnetic behavior in aqueous suspension (see Supporting Information File 1). Fe-Ni/Zn and Fe-Ni/Zn/βCD nanoparticles morphologies were investigated in the solid state by scanning electronic microscopy (SEM), transmission electronic microscopy (TEM), and atomic force

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

• such as gel-permeation chromatography (GPC), or through a combination of these methods. Product purity and ligand-grafting rates and ratios can be determined through the use of techniques such as NMR spectroscopy, thermal analysis (DSC/TGA), elemental analysis, and other spectroscopic techniques (e.g

• surface. Thermal analysis indicated three thermal events for hybrids Au@68–12 at ~85 °C, ~100 °C and ~150 °C (Table 1), with arguments based on thermochemical values suggesting that the first corresponded well to a melting transition, whereas the third event was reminiscent of a nematic-to-isotropic phase

• determined by 1H NMR analysis. Through thermal analysis, POM and miscibility experiments, the existence of the nematic phase was deduced (Table 2), as evidenced by the Schlieren and marbled textures observed under crossed polarisers (Figure 14). The success of this approach prompted further work involving a

Novel carbazole–pyridine copolymers by an economical method: synthesis, spectroscopic and thermochemical studies

• Aamer Saeed,
• Madiha Irfan and
• Shahid Ameen Samra

Beilstein J. Org. Chem. 2011, 7, 638–647, doi:10.3762/bjoc.7.75

• of P2a in THF at room temperature. Thermochemical properties of the polymers The thermal properties of the two series of polymers, P1 and P2 were investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). For TGA the samples were heated (PerkinElmer Thermal Analysis

• System 409) from 25 °C to 85 °C at a rate of 10 °C/min and at a nitrogen gas flow rate of 80 mL/min. Polymers P1 and P2 lost weight gradually during the early phase of the experiment. A thermal gravimetric analysis curve of P1a is shown in Figure 3. The thermal analysis results indicated that polymers P1

• and P2 have a high decomposition temperature Td and good thermal stability above 300 °C, which is very attractive for the fabrication of stable organic electroluminescent devices. TGA thermograms for polymers P1 and P2 are shown in Figure 4 and the results of the thermal analysis are shown in Table 1