5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• also investigated by techniques like fluorescence spectroscopy, single photon counting technique, cyclic voltammetry, thermogravimetric analysis, and DFT calculations. Boruah et al. [48][49] developed an efficient method for the construction of regioisomeric 1,3,4-trisubstituted pyrazolo[3,4-b

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

• good yields (Scheme 49). The oxidation–reduction potentials were determined by cyclic voltammetry and a catalytic cycle was proposed in which the CF3 radical was generated from CF3SO2Na via the organocatalyst AQN-2-CO2H and visible light (Scheme 49) [72]. Rueping’s group described three examples of

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• functionalities. Cyclic voltammetry was used for the electrochemical characterization of the QC (Figure S2, Supporting Information File 1), QC-Br5 (Figure S3), and CuIIBr2/tris(2-pyridylmethyl)amine (TPMA) in the absence (Figures S5 and S6) and in the presence of QC-Br5 (Figures S7 and S8), all the reaction

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

• Jan Podlesný,
• Lenka Dokládalová,
• Oldřich Pytela,
• Adam Urbanec,
• Milan Klikar,
• Numan Almonasy,
• Tomáš Mikysek,
• Jaroslav Jedryka,
• Iwan V. Kityk and
• Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

• ). Electrochemistry Electrochemical measurements of all target compounds were carried out in N,N-dimethylformamide containing 0.1 M Bu4NPF6 in a three electrode cell by cyclic voltammetry (CV) and rotating disk voltammetry (RDV). The working electrode was a platinum disk (2 mm in diameter) for CV and RDV experiments

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• electronegativity of fluorine and has been successfully isolated. In measurements of cyclic voltammetry, iron phthalocyanines with an alkoxy group show a lower first oxidation potential than unsubstituted iron phthalocyanine, but TFEO-FePc shows a more difficult oxidation process than unsubstituted iron

New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties

• Daria G. Selivanova,
• Alexei A. Gorbunov,
• Olga A. Mayorova,
• Alexander N. Vasyanin,
• Igor V. Lunegov,
• Elena V. Shklyaeva and
• Georgii G. Abashev

Beilstein J. Org. Chem. 2017, 13, 1583–1595, doi:10.3762/bjoc.13.158

• properties of the prepared compounds were investigated by UV–vis absorption spectroscopy and cyclic voltammetry. Electrochemical oxidation of these heterocycles resulted in the formation of thin films on the surface of an ITO working electrode. The morphology of grown films has been investigated by means of

• mechanism has been described in detail by K. Karon et al. [33]. Electrochemical properties of the obtained compounds were investigated by cyclic voltammetry (CV). The measurements were carried out for MeCN/CH2Cl2 (9:1) solutions containing Et4NClO4 (c = 10−3 mol L−1) as a supporting electrolyte in a three

Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications

• Vinila N. Viswanathan,
• Arun D. Rao,
• Upendra K. Pandey,
• Arul Varman Kesavan and
• Praveen C. Ramamurthy

Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87

• experimental values obtained by UV–vis spectroscopy. Here it is observed that both the HOMO–LUMO values and the electronic transition wavelengths of the polymers showed promising results for OPV applications. The HOMO–LUMO energy levels of the polymers were determined by cyclic voltammetry, using non-aqueous

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

• Matthias C. Letzel,
• Hans J. Schäfer and
• Roland Fröhlich

Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5

• -coupling product of carboxylic acid 18 was found, but polar compounds were obtained, whose structures were not determined. To explain this failure, it is assumed that under the electrolysis conditions the electron-rich aromatic ring system is preferentially oxidized. Cyclic voltammetry of the malonates 15a

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

• as-cast film emission. Detailed variable temperature X-ray analysis of BQR thin films is currently underway to better understand these changes. CV and PESA: The electrochemical properties of the BXR series of materials have been examined by cyclic voltammetry (CV), photoelectron spectroscopy in air

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• cyclization synthesis of symmetrically 2,5-diaryl-substituted thiophenes is excellently suited to access thienyl-bridged oligophenothiazines in a one-pot fashion. Three thienyl-bridged systems were intensively studied by UV–vis and fluorescence spectroscopy as well as by cyclic voltammetry. The oxidation

• ; copper; cyclic voltammetry; DFT; microwave-assisted synthesis; multicomponent reactions; palladium; phenothiazines; thiophenes; Introduction Oligothiophenes [1][2][3][4][5][6][7][8] have adopted a dominating role among functional π-electron systems [9]. In particular, they have received attention as

• characterization by electronic spectroscopy, cyclic voltammetry, and quantum chemical computations. Results and Discussion Synthesis of thienyl-bridged oligophenothiazines Although the thienyl bridge can be introduced by Suzuki coupling as previously reported [48], we decided to transpose a methodology initiated

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• are observed at 669 and 800 nm, respectively. Compared to λmax of BF2(WS3), BF2(L4) exhibits a large hypsochromic shift of 33 nm. Electrochemistry Cyclic voltammetry of the zinc(II) and BF2+ chelates was studied in dichloromethane solutions using ferrocene/ferricinium (Fc/Fc+) as an internal reference

• and L3 chelates. The estimated HOMO and LUMO energy levels obtained from cyclic voltammetry are shown in Figure 8. The HOMO and LUMO of Zn(L1)2 and Zn(L4)2 approach those of PCBM. Crystallography Single crystals of the zinc(II) chelates were grown in order to better understand the structure of the

• Q500 thermogravimetric analyzer. Cyclic voltammetry was performed at room temperature using an Auto-Lab-PGSTAT 302N, Exo Chemie potentiostat. Dichloromethane (DCM) was dried over calcium hydride and stored in a nitrogen glove box prior to use. The samples were prepared in a degassed 0.1 M solution of

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• , azulene→terpy, though different functionals are not consistent in depicting the contributing ratios of these various components of electronic transitions. Electrochemical properties The redox properties of 4a and 4b were investigated using cyclic voltammetry (CV) and differential pulse voltammetry (DPV

• and instruments All reagents for performing the chemical reactions were used as received. CH2Cl2 for fluorescence measurements was purchased from Merck. Dimethylformamide for cyclic voltammetry measurements was purchased from Sigma-Aldrich and kept over molecular sieves. Column chromatography was

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• derivatives reported in the literatures [21][23]. Electrochemical properties Cyclic voltammetry (CV) was applied to investigate the energy levels of 1–4. The cyclic voltammograms of these four compounds are presented in Figure 2 and the electrochemical data are listed in Table 1. As can be seen from Figure 2

Cp₂TiCl/D₂O/Mn, a formidable reagent for the deuteration of organic compounds

• Antonio Rosales and
• Ignacio Rodríguez-García

Beilstein J. Org. Chem. 2016, 12, 1585–1589, doi:10.3762/bjoc.12.154

• cyclic voltammetry, theoretical calculations and electro-paramagnetic resonance techniques studies [28][34]. These results are in agreement with the previously reported results by Wood et al. [35] and Renaud et al. [36] describing the effect of complexation with a Lewis acid on the strength of the O–H

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• from the solution to thin film states implied the presence of strong intermolecular interactions between the polymer backbones. Cyclic voltammetry (CV) of the polymer thin films was measured in CH3CN with 0.1 M (n-C4H9)4NPF6 as the supporting electrolyte at 20 °C. Both polymers displayed irreversible

• -View Analyst software was used to model the Nyquist plots obtained from the impedance measurements. (a) Normalized UV–vis absorption of Cbz-EDOT polymers in CH2Cl2 measured at 10−5 M repeat unit−1 and in thin films and (b) cyclic voltammetry of Cbz-EDOT polymer films on glassy carbon electrode

On the mechanism of imine elimination from Fischer tungsten carbene complexes

• Philipp Veit,
• Christoph Förster and
• Katja Heinze

Beilstein J. Org. Chem. 2016, 12, 1322–1333, doi:10.3762/bjoc.12.125

• platinum wire as counter electrode and a 0.01 M Ag/AgNO3 electrode as reference electrode. The measurements were carried out at a scan rate of 100 mV s−1 for cyclic voltammetry experiments and at 50 mV s−1 for square wave voltammetry experiments in 0.1 M [n-Bu4N][B(C6F5)4] as supporting electrolyte in THF

Separation and identification of indene–C₇₀ bisadduct isomers

• Bolong Zhang,
• Jegadesan Subbiah,
• David J. Jones and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2016, 12, 903–911, doi:10.3762/bjoc.12.88

• various fractions of IC70BA is shown in Table 1. In order to analyze the electrochemical properties of the IC70BA fractions, cyclic voltammetry was performed on each fraction. The first reduction potentials of all 11 fractions were found to be in the range of −1.13 to −1.25 eV versus that of ferrocene

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• as dibenzo[d,d']benzo[2,1-b:3,4-b']difuran (syn-DBBDF) and dinaphtho[2,3-d:2',3'-d']benzo[2,1-b:3,4-b']difuran (syn-DNBDF) were synthesized. Their photophysical and electrochemical properties were revealed by UV–vis absorption and photoluminescence spectroscopy and cyclic voltammetry. Organic field

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• ) and heptakis-(2,3,6-tri-O-methyl)-β-cyclodextrin (TRIMEB CD) were investigated by different spectroscopic techniques (UV–vis, FTIR–ATR, 1H NMR) and cyclic voltammetry analysis (CV). This work is necessary for a prospective research on the photoreactivity of S4TdR in aqueous environment and in the

• involved, more details were searched through the use of cyclic voltammetry (CV), FTIR–ATR and 1H NMR analysis. Cyclic voltammetry analysis As described in [33], the clear formation of inclusion complexes between S4TdR and all employed CDs was investigated by means of electrochemical analyses. In fact, if

• the employed CDs interact with S4TdR, different electrochemical properties would be expected, as described in [36]. The obtained results are reported in Figure 3. When a S4TdR solution is measured with cyclic voltammetry a well-defined irreversible cathodic peak, located at −1.39 V, appeared and was

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• macromolecular chains and the macrocycles, 3, 3·TM-βCD and 3·TM-γCD were electrochemically investigated by cyclic voltammetry (CV), Figure 4 and the results are summarized in Table 2. The Ep,onset and En,onset values allow the estimation of the ionization potential (IP), electron affinity (EA) and energy band

Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-MIC ligand. Study of the electronic properties and catalytic activities

• Carmen Mejuto,
• Beatriz Royo,
• Gregorio Guisado-Barrios and
• Eduardo Peris

Beilstein J. Org. Chem. 2015, 11, 2584–2590, doi:10.3762/bjoc.11.278

• -NHC ligand. The electronic properties of the tris-MIC ligand were studied by cyclic voltammetry measurements. In all cases, the tris-MIC ligand showed a stronger electron-donating character than the corresponding NHC-based ligands. The catalytic activity of the tri-rhodium complex was tested in the

• B, cyclic voltammetry studies of 2 and 3 (Figure 1) and 4 (Figure 2) were performed. The rhodium complex 2 showed an irreversible wave at E1/2 = 0.56 mV, while the iridium complex 3 displayed a pseudo-reversible wave at a half-wave potential of E1/2 = 0.63 mV. Compared to the cyclic voltammetry data

• both complexes 2 and 3 is consistent with the electronic disconnection of the three metals in both trimetallic complexes. The cyclic voltammetry diagram of the tri-Ni(II) complex 4 is shown in Figure 2, together with the differential pulse voltammetry (DPV) plot. The complex shows a quasi-reversible

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• shown in Figure 4c–e. In contrast to those of T1 and T2, the N–H and C=O stretching bands of the amide groups were not obviously shifted after doping with TCNQ. This indicated that the doping did not change the hydrogen-bonded structures. Cyclic voltammetry (CV) The cyclic voltammetry experiments were

• hydrogen bonds between urethane groups and the π–π stacking interaction from TTF units were regarded as the main driving forces behind the self-assembly process. Cyclic voltammetry showed that the TTF derivatives underwent two reversible oxidation processes. In addition, the doping of nanoribbons by TCNQ

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

• Vasily M. Muzalevskiy,
• Aleksei V. Shastin,
• Alexandra D. Demidovich,
• Namiq G. Shikhaliev,
• Abel M. Magerramov,
• Victor N. Khrustalev,
• Rustem D. Rakhimov,
• Sergey Z. Vatsadze and
• Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2015, 11, 2072–2078, doi:10.3762/bjoc.11.223

• , with polyhaloalkanes. The procedure is simple, cheap and could be applied for the utilization of environmentally harmful polyhalocarbons. The cyclic voltammetry study of the representative examples of the synthesized ferrocenyl alkenes shows the strong dependence of the cathodic behavior on the amount

• of vinyl groups: while for the monoalkene containing molecules no reduction is seen, the divinyl products are reduced in several steps. Keywords: catalytic olefination; copper catalysis; cyclic voltammetry; ferrocene; Introduction The introduction of complex functional fragments into the specified

• at a double bond. Three representative groups of halovinylferrocenes were studied using cyclic voltammetry (Table 1). The first group was formed from three omega-dichloro derivatives 1, 6, and 10. The second one was made from three omega-dibromo products 2, 7, and 11, and the last group consisted of

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• group, avoiding the effect of steric interactions between pendant TTF units and increasing the conjugation length of the PT backbone (Scheme 2). They successfully electropolymerised TTF-modified thiophene monomer 5a to polymer 6a from a nitrobenzene monomer solution [48]. Cyclic voltammetry of the

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• self-aggregated in chloroform–dioxane to form a gel. TEM images of the xerogel exhibited helical molecular tapes nanometer wide and micrometer long. A cyclic voltammetry (CV) study on 2b showed the redox properties expected for Pc and TTF, and doping of 2b in CH2Cl2 with I2 produced a radical cation

• . The intramolecular through-bond interaction between the two TTF parts linked in a head-to-tail manner is calculated to be weak in the ground state [25]. Thus, the conjugation of the two neutral TTF parts in 16–19 is weak (Figure 6) [59]. In the cyclic voltammetry (CV) measurements, tetraethylthio-bi

• parameters of 23 in various solventsa. Self-aggregation data in toluene-d8.a Redox potentials of 28–34 measured by CVa. Supporting Information Supporting Information File 228: Determination of association constants (K2) of 23 by NMR and cyclic voltammetry analysis of 23. Acknowledgements This work was