Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162

• their HOMO/LUMO energy levels were estimated by cyclic voltammetry measurements. Besides, density functional theory calculations were carried out for further exploration of their electronic properties. Keywords: catalysis; cross-coupling; cyclization; fluorescence; palladium; Introduction π-Conjugated

• cyclic voltammetry (CV) in dry acetonitrile. The obtained voltammogram, recorded at a scanning rate of 50 mV/s, is given in Figure 11. The HOMO and LUMO energy levels were deduced from the onset potentials of the oxidation and reduction waves, respectively. The potential of the saturated Ag/AgCl

• PC spectrophotometer in quartz cuvettes with a path length of 1 cm. Emission spectra were recorded on a Perkin-Elmer LS 50B spectrofluorimeter. Cyclic voltammetry was performed in anhydrous acetonitrile solution containing 0.1 M of tetrabutylammonium tetrafluoroborate (n-Bu4NBF4) as a supporting

Icilio Guareschi and his amazing “1897 reaction”

• Gian Cesare Tron,
• Alberto Minassi,
• Giovanni Sorba,
• Mara Fausone and
• Giovanni Appendino

Beilstein J. Org. Chem. 2021, 17, 1335–1351, doi:10.3762/bjoc.17.93

• alcohol side product was not labeled, suggesting that alcohols are formed by radical trapping by oxygen and the intermediate formation of hydroperoxides. Conversely, cations would have been trapped by water, resulting in the formation of labeled alcohols. Cyclic voltammetry experiments showed an

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

• Mio Matsumura,
• Takahiro Teramoto,
• Masato Kawakubo,
• Masatoshi Kawahata,
• Yuki Murata,
• Kentaro Yamaguchi,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56

• –426 nm (Table 2). P-methylated cation 5 exhibited the longest wavelength and the highest quantum yield. The electrochemical properties of benzonaphthophosphoindoles were investigated by using cyclic voltammetry, and the electrochemical data are summarized in Table 3 and Figure S4, Supporting

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• % yield [100]. Photolysis of derivatives of para-substituted 3-fluoromethyl-3-phenyldiazirones in the presence of C60 gave phenylmethanofullerenes 53–56 in acceptable yields (Scheme 17) [101]. The electrochemical properties of the products were characterized by cyclic voltammetry and differential pulse

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• transfer (MLCT), and intraligand charge transfer (ILCT) transitions were identified. The vis–NIR spectroscopy revealed that in complex 17 the metal-to-ligand stoichiometry is equal to 1:1. In turn, cyclic voltammetry was used to investigate the electrochemical behavior of complex 17. The measurements on a

• Information File 65: Experimental details, synthetic procedures, and characterization data of new compounds including copies of spectra. Supporting Information File 66: Experimental details, computational details, X-ray crystallographic data, FTIR and vis–NIR spectra, and cyclic voltammetry for compounds 7

Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands

• Sergey V. Norkov,
• Anton V. Cherkasov,
• Andrey S. Shavyrin,
• Maxim V. Arsenyev,
• Viacheslav A. Kuropatov and
• Vladimir K. Cherkasov

Beilstein J. Org. Chem. 2021, 17, 273–282, doi:10.3762/bjoc.17.26

•  1 summarizes the results of the electrochemical studies. Usually, the electrochemistry of sterically hindered o-quinones is relatively simple, it includes two one-electron steps with separation of potentials. Cyclic voltammetry studies reveal that the reduction of 3a, 6a and 7 takes place in two

Controlled decomposition of SF₆ by electrochemical reduction

• Sébastien Bouvet,
• Bruce Pégot,
• Stéphane Sengmany,
• Erwan Le Gall,
• Eric Léonel,
• Anne-Marie Goncalves and
• Emmanuel Magnier

Beilstein J. Org. Chem. 2020, 16, 2948–2953, doi:10.3762/bjoc.16.244

• = 0.00 ppm) for 19F (188 or 282 MHz) NMR spectra. The 19F NMR of the final mixture was recorded after concentration under vacuum to see a broad fluoride signal. (a) Cyclic voltammetry onto microelectrode arrays (Ø = 20 µm) in acetonitrile freshly distilled after the addition of TBAClO4 (0.1 M) at room

Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• planar and conformationally restricted systems [48]. In order to get information about the redox properties and energetics of the frontier orbitals, the S,N-heteroacenes were studied by cyclic voltammetry and all potentials were referenced against the ferrocene/ferricenium couple (Table 1). In the series

Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes

• Henrik Hupatz,
• Marius Gaedke,
• Hendrik V. Schröder,
• Julia Beerhues,
• Arto Valkonen,
• Fabian Klautzsch,
• Sebastian Müller,
• Felix Witte,
• Kari Rissanen,
• Biprajit Sarkar and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2020, 16, 2576–2588, doi:10.3762/bjoc.16.209

• electrochemical analytical tools, e.g., cyclic voltammetry (CV), exhibit great potential to investigate the kinetic and thermodynamic parameters of the switching processes [32][33]. Although various redox-active crown ethers have been described [14][21][34], they are not commonly implemented into crown ether

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• -containing rotaxane 1a was studied by cyclic voltammetry in CH2Cl2/CH3CN 1:5 (v/v) using a three-electrode cell, with a glassy carbon working electrode, a silver wire counter electrode and an Ag/AgCl (3 M KCl) reference electrode. Tetrabutylammonium hexafluorophosphate was used as the supporting electrolyte

• -diaminomethylbenzene molecules, in the presence of a suitable hydrogen-bonding template. Among the different templates employed, 4a proved to be the most successful giving rise to rotaxane 1a in 41% yield. Meanwhile, 4b and 4c gave little or no rotaxane formation. Cyclic voltammetry showed that the electroactive

• voltage was maintained at 3200 V and the capillary temperature set to 320 °C. Samples were introduced by injection through a 20 µL loop into a 300 µL/min flow of methanol from the LC pump. Electrochemistry: Cyclic voltammetry was carried out in a Metrohm Autolab PGSTAT302N potentiostat using a three

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• compounds, based on theoretical calculations and experimental measurements, as well as the electrochemical and thermal properties, are discussed. The synthesized compounds form glasses with glass-transition temperatures ranging from 116 °C to 123 °C. The ionization potentials estimated by cyclic voltammetry

• substituents of the quinazoline derivatives 1–3, whereas the LUMO energies were close and characteristic of the quinazoline unit. The electron-donating characteristics were investigated experimentally by cyclic voltammetry (CV). All three compounds showed reversible oxidation (Figure 3) and the data are

• nucleophilic aromatic substitution reaction. The dimethyldihydroacridine and phenothiazine-containing quinazoline compounds formed molecular glasses with glass-transition temperatures of 123 °C and 116 °C, respectively. The ionization potentials estimated by cyclic voltammetry of the derivatives were found to

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

• Nuray Altinolcek,
• Ahmet Battal,
• Mustafa Tavasli,
• William J. Peveler,
• Holly A. Yu and
• Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

• spectroscopy, mass spectrometry, FTIR, thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and absorption and emission spectroscopy. Compounds 7a and 7b, both of which were amorphous solids, were stable up to 291 °C and 307 °C, respectively. Compounds 7a and 7b show three

• of compounds 7a and 7b are depicted in Figure 1. Thermal properties of compounds 7a and 7b are also summarised in Table 1. Electrochemical properties The redox behaviour of compounds 7a and 7b was investigated by cyclic voltammetry in dichloromethane solution under argon atmosphere using

Aryl-substituted acridanes as hosts for TADF-based OLEDs

• Naveen Masimukku,
• Dalius Gudeika,
• Oleksandr Bezvikonnyi,
• Ihor Syvorotka,
• Rasa Keruckiene,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

• derivatives 3–6 were investigated by cyclic voltammetry (CV). The cyclic voltammograms of compounds 3–6 are shown in Figure 4a and Figure S2 of Supporting Information File 1, and the data are collected in Table 2. Close values for the potentials of reversible oxidation of ca. 0.3–0.4 V were observed for the

• ] and Gaussview 6 software. The ionization potential measurements of the solid samples were performed by the photoelectron emission method in air [36]. Cyclic voltammetry (CV) measurements of the liquid samples were carried out as described earlier [37]. Charge drift mobility measurements for the

• 3–6. Electroluminescence characteristics of OLEDs. Supporting Information Supporting Information File 286: Charge drift mobility measurements, TGA curves of 3–6, cyclic voltammetry data of 4–6, TOF and CELIV current transients for 4, 5, and 6, current efficiency, and power efficiency versus current

Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes

• Aya Yoshimura,
• Hitoshi Kimura,
• Kohei Kagawa,
• Mayuka Yoshioka,
• Toshiki Itou,
• Dhananjayan Vasu,
• Takashi Shirahata,
• Hideki Yorimitsu and
• Yohji Misaki

Beilstein J. Org. Chem. 2020, 16, 974–981, doi:10.3762/bjoc.16.86

• peripheral part of TTF. The LUMO of 1a spread over the whole molecule except the outer 1,3-dithiole rings. The orbital energy of the HOMO of 1a (−4.41 eV) was slightly higher than that of TTF (−4.57 eV). As such, the first oxidation of 1a might occur at a lower potential than TTF [43]. Cyclic voltammetry

• analysis The redox behavior of 1–4 was investigated by cyclic voltammetry. The compounds 1a and 1b exhibited four and three pairs of redox waves, respectively (around +0.03, +0.10, +0.17, and +0.42 V vs Fc/Fc+ for 1a and −0.05, +0.10, and +0.46 V vs Fc/Fc+ for 1b, Figure 4). The redox potentials of 1a,b

Copper catalysis with redox-active ligands

• Agnideep Das,
• Yufeng Ren,
• Cheriehan Hessin and
• Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

• another family of galactose oxidase mimics based on copper(II) complex 4 bearing a non-innocent iminophenol-iminopyridine hybrid ligand 3 that performed two-electron oxidations of primary alcohols to aldehydes (Scheme 2) [15]. Catalyst 4 was fully characterized by combined EPR, cyclic voltammetry and

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation

• Ji Ma,
• Yubin Fu,
• Junzhi Liu and
• Xinliang Feng

Beilstein J. Org. Chem. 2020, 16, 791–797, doi:10.3762/bjoc.16.72

• 1.78 eV from the onset of its UV–vis absorption spectrum. Similar to the cyclopenta-fused pyrene derivatives [28][29], compound 1 does not show detectable fluorescence emission. Furthermore, the electrochemical properties of 1 was probed by cyclic voltammetry (CV) in DCM (Figure 3b). According to the

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• substituted BODIPY cores, higher emission quantum yields of 0.86 and 0.77 were estimated, respectively (Table 1). Electrochemical properties Cyclic voltammetry and differential pulse voltammetry of the BODIPY derivatives 3a–6a were performed in dichloromethane solutions containing 0.1 M tetra-n-butylammonium

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

• Mingbing Zhong,
• Xavier Pannecoucke,
• Philippe Jubault and
• Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

• and co-worker described the synthesis of a new heteroleptic copper complex bearing a substituted bipyridine ligand (Scheme 18) [34]. The novel copper catalyst was fully characterized by X-ray crystallographic analysis, UV–visible absorption and emission as well as cyclic voltammetry. The catalyst [Cu

• , probably due to their intrinsic reduction potential. Interestingly, the bromide substrate derived from menthol was readily reduced in an excellent 74% isolated yield. The authors conducted some mechanistic studies (including cyclic voltammetry and Stern–Volmer quenching experiments, for instance), and

Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid

• Kaj M. van Vliet,
• Nicole S. van Leeuwen,
• Albert M. Brouwer and
• Bas de Bruin

Beilstein J. Org. Chem. 2020, 16, 398–408, doi:10.3762/bjoc.16.38

• contains a carboxyl group that could perhaps be oxidatively decarboxylated to generate a chloromethyl radical. In this study, we investigated the possibility of redox neutral, visible light photoredox catalyzed C–C bond formation with monochloroacetic acid. Results and Discussion First, we used cyclic

• voltammetry to determine the oxidation potential (EOx) of monochloroacetic acid in acetonitrile (Figure 2). This way it could be verified, if monochloroacetic acid can quench the excited state of one of the common photoredox catalysts. In Figure 1 the cyclic voltammogram of monochloroacetic acid is shown. One

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• efficient brominations, they employed sodium bromide in the presence of oxygen. The activation of the photocatalyst through protonation was shown by cyclic voltammetry, and the other interactions were revealed by emission quenching experiments and UV–vis spectroscopy. As can be seen in Scheme 21, the group

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

• Daniel R. Sutherland,
• Nidhi Sharma,
• Georgina M. Rosair,
• Ifor D. W. Samuel,
• Ai-Lan Lee and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

• enhanced overlap of the HOMO and LUMO wave functions. Electrochemical properties The electrochemical behavior of 2–5 was studied by cyclic voltammetry and differential pulse voltammetry in degassed DCM with tetrabutylammonium hexafluorophosphate as the supporting electrolyte. The cyclic voltammograms (CVs

Experimental and computational electrochemistry of quinazolinespirohexadienone molecular switches – differential electrochromic vs photochromic behavior

• Eric W. Webb,
• Jonathan P. Moerdyk,
• Kyndra B. Sluiter,
• Benjamin J. Pollock,
• Amy L. Speelman,
• Eugene J. Lynch,
• William F. Polik and
• Jason G. Gillmore

Beilstein J. Org. Chem. 2019, 15, 2473–2485, doi:10.3762/bjoc.15.240

• cyclic voltammetry and 1H NMR analyses, in concert with computational modeling. These results are compared to those for the symmetric parent PSHD, which due to symmetry possesses only a single possible regioisomer upon either electrochemical or photochemical ring-opening. Density functional theory

• calculations of bond lengths, bond orders, and molecular orbitals allow the rationalization of this differential photochromic vs electrochromic behavior of the QSHDs. Keywords: cyclic voltammetry; density functional theory; heterocycles; molecular switches; photochromic photooxidants; spirocycles

• ] for 1a (Scheme 1). Electrochemically, they report observing a single, two-electron reduction peak and two distinct one-electron oxidation peaks upon scanning using cyclic voltammetry. They therefore proposed [10] that the electrolysis of 1a proceeds by an “ECE” (electrochemical-chemical

Small anion-assisted electrochemical potential splitting in a new series of bistriarylamine derivatives: organic mixed valency across a urea bridge and zwitterionization

• Keishiro Tahara,
• Tetsufumi Nakakita,
• Alyona A. Starikova,
• Takashi Ikeda,
• Masaaki Abe and
• Jun-ichi Kikuchi

Beilstein J. Org. Chem. 2019, 15, 2277–2286, doi:10.3762/bjoc.15.220

• electrochemical behavior of 1a and 1b having two chemically equivalent NAr3 units was investigated by cyclic voltammetry and differential pulse voltammetry. Interestingly, two reversible waves were observed for 1b in CH2Cl2 containing 0.10 M n-Bu4NPF6 (Figure 2, bottom, and Table 1 and Table S3 in Supporting

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• 1H NMR titration experiments in CD3CN solution and cyclic voltammetry in 0.1 M TBA·PF6 (TBA = tetrabutylammonium) in CH3CN (Figure 3). WinEQNMR2 analysis of the titration data has revealed that among the tested anions, the receptor 4 binds strongly with chloride and benzoate ions through favorable

• charge-assisted C–H···anion interactions. According to the cyclic voltammetry analysis, the redox-active macrocycle was able to recognize chloride, causing a cathodic shift of the Epa wave of the ferrocene/ferrocenium redox couple. However, a quick disappearance of the redox signal was observed when the