Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis

• Tatiana Golub and
• James Y. Becker

Beilstein J. Org. Chem. 2018, 14, 861–868, doi:10.3762/bjoc.14.72

• , Scheme 7) and the outcome from their preparative electrolysis (at constant current) under different experimental conditions, as a function of the length of spacer between the two amide functionalities. Results and Discussion The electrochemical properties of the bisamides described in Scheme 6 were

• pharmaceutical compounds. For instance, symmetrical and unsymmetrical bisamides derived from diamines are significant components as structural subunits for the construction of peptidomimetric frameworks [18] and as lubricants [19]. To the best of our knowledge nothing has been known so far about electrochemical

• properties of α,ω-bisamides derived from α,ω-diaminoalkanes. However, notably that the bisamide 3,5-diaza-2,6-heptanedione was obtained from N-methylacetamide by electrolysis on a Pt anode in water [20]. The present work describes the electrochemical behavior of eight synthesized bisamides (from diamines

D–A–D-type orange-light emitting thermally activated delayed fluorescence (TADF) materials based on a fluorenone unit: simulation, photoluminescence and electroluminescence studies

• Lin Gan,
• Xianglong Li,
• Xinyi Cai,
• Kunkun Liu,
• Wei Li and
• Shi-Jian Su

Beilstein J. Org. Chem. 2018, 14, 672–681, doi:10.3762/bjoc.14.55

• fabrication of OLEDs. In order to characterize their electrochemical properties, cyclic voltammetry (CV) measurements were conducted to measure their oxidation potentials (Eox) and reduction potentials (Ered). Ionization potential (IP) and electron affinity (EA), which approximate to their HOMO and LUMO

• simulated EQE by employing the TTA model. Molecular structures of isomers 1 and 2. Thermal and electrochemical properties of the investigated compounds 1 and 2. The calculated HOMO, LUMO, twisting angles (θ, θ’), bond lengths (l, l’), ΔEST and dipole moment in gas phase for S0 and in solution for S1, from

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

• Baris Temelli and
• Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

• ], subporphyrin [27] and expanded porphyrins [28][29][30] were prepared and their photophysical and electrochemical properties were characterized. Among these compounds, corroles, contracted porphyrin analogues [31][32][33], assumed an important place in porphyrin chemistry due to their small cavities, trianionic

Ni nanoparticles on RGO as reusable heterogeneous catalyst: effect of Ni particle size and intermediate composite structures in C–S cross-coupling reaction

• Debasish Sengupta,
• Koushik Bhowmik,
• Goutam De and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 1796–1806, doi:10.3762/bjoc.13.174

• nanocomposites [30]. Therefore, RGO is considered an excellent candidate for catalyst support [31][32]. To date, various magnetic or semiconducting nanoparticles (NPs) have been incorporated in GO surfaces and thoroughly studied in terms of their photocatalytic and electrochemical properties [33][34][35][36][37

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

• incorporation of such moieties changes the optical and electrochemical properties of the resulted conjugated systems [5]. Another effective way to change the properties of a conjugated system involves the modification of substituents attached to a nitrogen atom of the carbazole unit [8]. The long-chain alkyl

• region characterizing π–π* electron transitions and a low-intensity absorption maxima (at 535 nm for 8a and at 540 nm for 8b) which corresponds to the effective intramolecular charge transfer, are typical for this series of compounds. Electrochemical properties of the synthesized compounds The

• 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

Interactions between shape-persistent macromolecules as probed by AFM

• Johanna Blass,
• Jessica Brunke,
• Franziska Emmerich,
• Cédric Przybylski,
• Vasil M. Garamus,
• Artem Feoktystov,
• Roland Bennewitz,
• Gerhard Wenz and
• Marcel Albrecht

Beilstein J. Org. Chem. 2017, 13, 938–951, doi:10.3762/bjoc.13.95

• polymers have been reported so far, including CD-modified conjugated oligomers and polymers composed of rigid phenylene ethynylene (PPE) structure units which are able to form self-inclusion complexes with tunable electrochemical properties [29][30][31][32][33][34][35]. The synthesis of PPE, in which two β

Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

• Anastasia S. Kostyuchenko,
• Tatyana Yu. Zheleznova,
• Anton J. Stasyuk,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2017, 13, 313–322, doi:10.3762/bjoc.13.34

• frequently combine solution processability with unique electronic, luminescent and electrochemical properties [1][2][3][4][5]. Molecules in which a central electron-accepting ring separates two bithiophene units are of particular interest [6][7][8][9][10][11][12][13][14][15]. The continuing progress in this

• ]. We have also shown that these molecules, if the α-position in the terminal polymer ring is not blocked, can electrochemically polymerize yielding either linear polymers [17][19][20][24] or polymeric networks [23]. It has been demonstrated that the optical and electrochemical properties of these new

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

• Xiao Huang,
• Li Yang,
• Rikard Emanuelsson,
• Jonas Bergquist,
• Maria Strømme,
• Martin Sjödin and
• Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

• ether linkage. Furthermore, substantial differences between ProDOT and EDOT polymers regarding their electrochemical properties have been described [29]. Scheme 2 shows the synthesis of pyEDOT 3. It starts with glycidol that can be economically prepared by the epoxidation of allyl alcohol [30]. The

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

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

• chelated with zinc(II) and BF2+ and the optical and electrochemical properties were studied. Fluorination had little effect on the optical properties of both the zinc(II) and BF2+ complexes, with λmax in solution around 755 nm and 785 nm, and high molar absorptivities of 100 × 103 M−1cm−1 and 50 × 103 M

• derivatives were then chelated with both BF2+ and zinc(II) (Scheme 2, see below), and their optical and electrochemical properties were studied. The BF2+ chelates were included in this study because they may be useful near-IR absorbers for other light-harvesting applications. The fluorine substitutions had

• little effect on the optical properties of the BF2+ and zinc(II) chelates, and only had a small effect on the electrochemical properties, with the largest increase in oxidation and reduction potentials of 0.1 V observed for L1 and L4 chelates compared to WS3 chelates. Zinc(II) chelates of L1 and L4 are

Experimental and theoretical investigations on the high-electron donor character of pyrido-annelated N-heterocyclic carbenes

• Michael Nonnenmacher,
• Dominik M. Buck and
• Doris Kunz

Beilstein J. Org. Chem. 2016, 12, 1884–1896, doi:10.3762/bjoc.12.178

• -parameter [25][26][27][28], the 13C NMR chemical shift of special Pd(NHC)2 complexes [29][30], and electrochemical properties [31][32][33] (see [34][35] for reviews). In all these cases, only the overall donor-abilities of the NHC ligand are obtained. In the case of the Tolman parameter, not only the

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

• introducing conjugated moieties at the 4′-position [10][11][12]. In this context, the synthesis of tailored terpyridine derivatives with appropriate electron-donor/acceptor moieties may allow for a further improvement of their spectroscopic and electrochemical properties. Owing to its unique fluorescent and

• , 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

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

• ) as the π-conjugated bridge unit were synthesized. The optical and electrochemical properties of these compounds were systematically investigated. All these four compounds displayed broad absorption bands over 350–600 nm. The optical band gap becomes narrower (from 1.94 to 1.82 eV) and the HOMO energy

• molecular structure and properties of the conjugated molecules with BDT core, we report here a series of A–π–D–π–A-type conjugated molecules with a regioregular oligo(3-hexylthiophene) chain as the π-bridge unit. The optical and electrochemical properties of these compounds were systematically investigated

• 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

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• heterojunction solar cells. Even though PTzBDT-1 showed favourable optical and electrochemical properties, the devices based on this polymer present a power conversion efficiency of 3.3%, considerably lower than the efficiency of 4.7% obtained for the analogous solar cells based on PTzBDT-2. The lower

• collect it from the extraction thimble at the polymer purification stage while PTzBDT-2, was extracted with chloroform thanks to its better solubility. Optical and electrochemical properties The UV–visible absorption spectra of the pristine PTzBDT-1 and PTzBDT-2 polymers in dilute solution (in

• optical and electrochemical properties of the pristine polymer thin films as well as the photovoltaic performance of the corresponding solar cells. Indeed, the polymer with dihexylthiophene substituted BDT (PTzBDT-2) showed better solubility and hence formed a well-developed nanomorphology when mixed with

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

• -Cbz-EDOT, by Stille polycondensation. Despite the same chemical composition, 3,6-Cbz-EDOT and 2,7-Cbz-EDOT displayed different optical and electrochemical properties due to the different connectivity mode of the carbazole unit. Therefore, their performances as hole-transporting polymeric materials in

• , respectively, suggesting the successful copolymerization. Both polymers showed an explicit difference in their chemical shift values ascribed to the carbazole units due to the different connectivity patterns. In contrast, the IR spectra of the polymers were almost the same. Optical and electrochemical

• properties The UV–vis absorption spectra were employed to evaluate the optical properties of 3,6-Cbz-EDOT and 2,7-Cbz-EDOT. The spectra were measured in CH2Cl2 and in thin films (spin-coated on an ITO glass). The absorption maximum (λmax) of 3,6-Cbz-EDOT in CH2Cl2 was 362 nm, whereas the thin film showed the

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

• configuration were deduced using a variety of analytical techniques including 1H and 13C NMR and UV–vis spectroscopy. The electrochemical properties and the organic solar cell device performance were investigated for fractions where a reasonable quantity of sample could be isolated. Keywords: chromatographic

• 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

• physical and electrochemical properties of the synthesized compounds are also discussed. OFETs with these compounds as semiconducting layers were found to exhibit relatively high hole mobility of <1.0 × 10−1 cm2·V−1·s−1. Results and Discussion Synthesis The synthetic routes to syn-DBBDF 5 and syn-DNBDF 6

• -conjugation lengths than anti-isomers. Electrochemical properties Cyclic voltammograms of syn-DBBDF 5 and syn-DNBDF 6 are shown in Figure 4 [1.0 mM solution in CH2Cl2 (syn-DBBDF 5) or Cl2CHCHCl2 (syn-DNBDF 6) with 0.10 M Bu4NClO4], and the electrochemical properties were summarized in Table 1. syn-DBBDF 5

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

• 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

• attributed to the reduction of the thiocarbonyl group, (C4=S) (Figure 3, solid black line). In particular, as reported in [37] about the electrochemical properties of some thiones, the redox process involving the thionucleoside could be attributable to an electron transfer process centered on the C=S moiety

• mentioning that Equation 1 was used only in the case of 2-HP-CDs, the only case in which appreciable variations were observed concerning the electrochemical properties of the guest in the presence of CDs. As described in [40] the thermodynamic stability of the studied complexes, S4TdR and 2-HP-CDs, were

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

• carried out to explore the electrochemical properties of the TTF compounds. The cyclic voltammograms of T1 and T2 were measured in dry and degassed dichloromethane solution [28]. Both T1 and T2 displayed two, reversible, one-electron redox couples, in which the first oxidation at = +0.628 V (T1) and

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

• intermediates in the synthesis of ferrocene analogs of tamoxifen and other medicinally relevant molecules. Electrochemical properties of halovinylferrocenes The ferrocene unit possesses several exciting electrochemical characteristics, such as fast electron-transfer rate, low oxidation potential, and stability

• to the polymer support or to copolymerize it with the appropriate monomers. Therefore, we have also examined the electrochemical properties of the compounds obtained. It was shown that the oxidation of the ferrocene unit proceeds in accordance to the data found in literature, whereas the reduction

• and bis-alkenes was elaborated on the basis of a catalytic olefination reaction of N-unsubstituted hydrazones obtained from ferrocene-containing aldehydes and ketones. Electrochemical properties of synthesized alkenes were investigated and promising electrochemical characteristics were demonstrated

Synthesis of racemic and chiral BEDT-TTF derivatives possessing hydroxy groups and their achiral and chiral charge transfer complexes

• Sara J. Krivickas,
• Chiho Hashimoto,
• Junya Yoshida,
• Akira Ueda,
• Kazuyuki Takahashi,
• John D. Wallis and
• Hatsumi Mori

Beilstein J. Org. Chem. 2015, 11, 1561–1569, doi:10.3762/bjoc.11.172

• charge transfer complexes are also discussed. Results and Discussion Syntheses of racemic-1, enantiopure (S,S)- and (R,R)-2 and evaluation of their electrochemical properties The synthesis of the racemic trans-vic-(hydroxymethyl)(methyl)-BEDT-TTF (1) was performed in a similar manner to racemic 2 [22

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

• Rupert G. D. Taylor,
• Joseph Cameron,
• Iain A. Wright,
• Neil Thomson,
• Olena Avramchenko,
• Alexander L. Kanibolotsky,
• Anto R. Inigo,
• Tell Tuttle and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

• and electrochemical properties of compounds 1 and 2 have been measured by UV–vis spectroscopy and cyclic voltammetry and the results compared with density functional theory (DFT) calculations to confirm the observed properties. Organic field effect transistor (OFET) devices fabricated from 1 and 2

• incomplete reaction of all the bromine atoms), and this is attributed to the increased solubility of the intermediates, which in turn increases their statistical likelihood of reacting further. Optical and electrochemical properties The optical properties of TTFs 1 and 2 were analysed by solution state UV

• the synthesis of a half-unit and a final triethyl phosphite mediated homo-coupling. The resultant compounds, 1 and 2, were fully characterised and their optical and electrochemical properties elucidated via UV–vis spectroscopy and cyclic voltammetry, and explained in conjunction with DFT level

New tris- and pentakis-fused donors containing extended tetrathiafulvalenes: New positive electrode materials for rechargeable batteries

• Shintaro Iwamoto,
• Yuu Inatomi,
• Daisuke Ogi,
• Satoshi Shibayama,
• Yukiko Murakami,
• Minami Kato,
• Kazuyuki Takahashi,
• Kazuyoshi Tanaka,
• Nobuhiko Hojo and
• Yohji Misaki

Beilstein J. Org. Chem. 2015, 11, 1136–1147, doi:10.3762/bjoc.11.128

• TTF oligomers, because thiophene inserted precursors are more soluble than the TTF-type precursors as mentioned above. We succeeded in the synthesis of fused TTF pentamer and heptamer composed of the unit of 4 [20]. In this paper, we report the synthesis and electrochemical properties of vinyl

• HOMO–2 of TTPY (−5.439 eV). These results suggest that the electrons at the HOMO–2 of 5a and 6a and HOMO–4 of 8a might be removed more easily than those at the HOMO–2 of TTPY. Electrochemical properties The redox behaviors of 5d, 7d and 9d were investigated by using cyclic voltammetry. Deconvoluted

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• -empirical AM1 method in the case of 4 [19]. This distance was estimated to be equal to 9.7 Å indicating that this enlargement around 2 Å was the result mainly of the spatial contribution of the additional naphthoquinone spacer in molecular clip 4. Electrochemical properties The electrochemical behaviour of

• clip 4 is an efficient receptor for F4-TCNQ guest electron acceptor. This difference in binding interaction between host molecular clips 3 and 4 towards the F4-TCNQ guest could be explained by their electrochemical properties. By comparing the first oxidation potential of clips 3 and 4 with the first

• molecular clip using the N-tetraalkylation of glycoluril constitutes a powerful versatile method allowing an easy access to new architectures for which electrochemical properties can be tuned by simple modification of peripheral substituents on the TTF moiety. Cyclic voltammetry and spectroelectrochemical

Chiroptical properties of 1,3-diphenylallene-anchored tetrathiafulvalene and its polymer synthesis

• Masashi Hasegawa,
• Junta Endo,
• Seiya Iwata,
• Toshiaki Shimasaki and
• Yasuhiro Mazaki

Beilstein J. Org. Chem. 2015, 11, 972–979, doi:10.3762/bjoc.11.109

• . Moreover, the ECD intensities of both enantiomers did not change under ambient light, at least over several days. Therefore, 1,3-diphenylallene is a reliable chiral source for a chiral polymer having electron-donating units. The electrochemical properties of 3 and PTDPA were investigated by cyclic

• , electrochemical properties were also investigated by the CV method. Cationic species were prepared by the addition of Fe(ClO4)3 as the oxidant, and their UV and ECD spectra were also recorded. Other molecular designs, including a copolymer based on the 1,3-diphenylallene units, are currently underway to create