Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• . Supporting Information Supporting Information File 300: 1H NMR spectra of (S,S)-3 and (S,S)-1 and cyclic voltammogram of (S,S)-1. Acknowledgements This work was supported by the National Agency for Research (ANR, Project 09-BLAN-0045-01), the CNRS and the University of Angers.

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

• molecular clips 1–4 were determined using cyclic voltammetry experiments (Table 2). These studies displayed a different electrochemical behavior for clips 1, 2 and 3 in comparison to clip 4. In the latter case, the cyclic voltammogram (CV) showed two oxidation waves at Eapp0ox1 = +0.28 V and Eapp0ox2

• measurements demonstrated that the mixed-valence state in these fused glycoluril-TTF molecular clips seems to originate from intermolecular TTF interactions, according to measurements at various concentrations and to cyclic voltammogram simulations. Spatial and electrochemical properties were shown to be

Tuning the size of a redox-active tetrathiafulvalene-based self-assembled ring

• Sébastien Bivaud,
• Sébastien Goeb,
• Vincent Croué,
• Magali Allain,
• Flavia Pop and
• Marc Sallé

Beilstein J. Org. Chem. 2015, 11, 966–971, doi:10.3762/bjoc.11.108

• crystal structure of self-assembly M6L3. For clarity, H atoms and TfO− counteranions have been omitted. Geometry (from XRD) around two Pd centers in M4L2 (a) and M6L3 (b). The exTTF moieties have been cut for clarity. Cyclic voltammogram of L1 (c = 10−3 M, CH3CN/CH2Cl2 (v/v 50/50), 0.1 M n-Bu4NPF6, 100

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

• Yunfei Wang and
• Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

• electrochemical patterns can be seen in the cyclic voltammograms of carboxyl-DTF 7 and Zn-DTF complex 9 (Figure 2C and 2E); however, their redox potentials showed a slight degree of variation. Experimentally, the cyclic voltammogram of 9 was determined from its solid thin film compressed on the working electrode

• moieties (Figure 2B and 2D). In the cyclic voltammogram of Zn-TTFV coordination polymer 8 (measured from a solid film prepared in the same way as 9), the redox wave pair of TTFV is discernible but much weaker than that of Zn-DTF 9 (Figure 2F), suggesting that the electrochemical activity of the

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

• Sandrina Oliveira,
• Dulce Belo,
• Isabel C. Santos,
• Sandra Rabaça and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 951–956, doi:10.3762/bjoc.11.106

• drawn at 30% probability level with the atomic numbering scheme. Crystal structure of compound 3 viewed along the b axis. View of three neighbouring molecular stacks in 3. Cyclic voltammogram of 3. Synthesis of cyanobenzene-ethylenedithio-tetrathiafulvalene (CNB-EDT-TTF) 3. Redox potentials for donors

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

• Huixin Jiang,
• Virginia Mazzanti,
• Christian R. Parker,
• Søren Lindbæk Broman,
• Jens Heide Wallberg,
• Karol Lušpai,
• Adam Brincko,
• Henrik G. Kjaergaard,
• Anders Kadziola,
• Peter Rapta,
• Ole Hammerich and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

• form of the radical anion of 8 with a 14 πz aromatic core. In situ EPR−UV–vis–NIR cyclic voltammetry of 2b (1 mM) (a) potential dependence of difference vis–NIR spectra with the corresponding cyclic voltammogram (in CH2Cl2/0.1 M Bu4PF6, scan rate v = 2 mV s−1; the arrows indicate separation between the

• (red line) and double-integrated EPR intensity (black solid squares). In situ EPR−UV–vis–NIR cyclic voltammetry of 4 (0.4 mM): (a) potential dependence of difference vis–NIR spectra with corresponding cyclic voltammogram (in CH2Cl2/0.1 M Bu4PF6, scan rate v = 2 mV s−1); (b) selected vis–NIR spectra

TTFs nonsymmetrically fused with alkylthiophenic moieties

• Rafaela A. L. Silva,
• Bruno J. C. Vieira,
• Marta M. Andrade,
• Isabel C. Santos,
• Sandra Rabaça,
• Dulce Belo and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 628–637, doi:10.3762/bjoc.11.71

• collected: 25691, independent: 6102 (Rint = 0.0262), 390 parameters. The structure was solved by direct methods and refined by full-matrix least squares on F2; final R indices [I > 2sigma(I)]: R1 = 0.0173, ωR2 = 0.0420. CCDC 1051178. Cyclic voltammogram of α-tbtdt (1) and α-mtdt (2) (10−3 M) in

Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation

• Martin Weiser,
• Sergej Hermann,
• Alexander Penner and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2015, 11, 568–575, doi:10.3762/bjoc.11.62

• = 530 nm, 8–11 identified and quantified by GC–MS. Photocatalytic nucleophilic addition of alcohols to 1 and 6a. Photocatalytic experiments with 1 in flow reactorsa. Supporting Information Supporting Information File 394: Spectral data: Cyclic voltammogram of PDI, determination of E00 of PDI, Stern

IR and electrochemical synthesis and characterization of thin films of PEDOT grown on platinum single crystal electrodes in [EMMIM]Tf₂N ionic liquid

• Andrea P. Sandoval,
• Marco F. Suárez-Herrera and
• Juan M. Feliu

Beilstein J. Org. Chem. 2015, 11, 348–357, doi:10.3762/bjoc.11.40

• , respectively. The scan rate was 100 mV s−1 and the 50th scan is shown. b) Cyclic voltammogram of PEDOT on Pt(111) characterized in 0.1 M [EMMIM]Tf2N in acetonitrile. The total charge used during the PEDOT synthesis was 6.2 mC cm−2. The scan rate was 100 mV s−1. Chronoamperometry of PEDOT films synthesized on

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• /P3T-blend and the copolymer P(EDOT-co-3T)-1:1. During the electrochemical oxidation the homopolymers PEDOT and P3T both show chemically reversible behavior, but they differ significantly in their onset potentials of −0.8 V and 0.3 V vs Fc/Fc+, respectively (blue and red curves). The cyclic

• voltammogram (CV) of the PEDOT/P3T-blend has two current maxima located at −0.3 and +0.7 V. Both values correspond to the oxidation potentials of the respective homopolymers indicating the combination of the redox properties of PEDOT and P3T. The P(EDOT-co-3T)-1:1 film on the other hand shows one broad

3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates

• Aneta M. Tomkiel,
• Adam Biedrzycki,
• Jolanta Płoszyńska,
• Dorota Naróg,
• Andrzej Sobkowiak and
• Jacek W. Morzycki

Beilstein J. Org. Chem. 2015, 11, 162–168, doi:10.3762/bjoc.11.16

• ). The shapes of the voltammograms are similar (except 6f and 6g) to the one for 6β-isopropyloxy-3α,5α-cyclocholestane (6d), which is presented in Figure 1 (curve c, blue). The cyclic voltammogram for 6β-phenyloxy-3α,5α-cyclocholestane (6f) shows an additional anodic peak at 1.45 V (curve d, green) and

• the cyclic voltammogram for 6β-(4-hydroxyphenyloxy)-3α,5α-cyclocholestane (6g) shows two additional anodic peaks at 0.88 V and 1.45 V (curve e, brown). The existence of these peaks is probably connected with electrooxidation of the substituents. It is worth to notice that in the case of 6f and 6g the

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• analysis of the molecular orbitals in compounds 9 and 10, can help to determine why the reduction wave of the cyclic voltammogram is more negative for compound 10, despite the increase in conjugation. The SOMO of the radical anion of each compound is localised on a BODIPY unit (Figure 8), meaning reduction

An integrated photocatalytic/enzymatic system for the reduction of CO₂ to methanol in bioglycerol–water

• Michele Aresta,
• Angela Dibenedetto,
• Tomasz Baran,
• Antonella Angelini,
• Przemysław Łabuz and
• Wojciech Macyk

Beilstein J. Org. Chem. 2014, 10, 2556–2565, doi:10.3762/bjoc.10.267

• )(H2O)]2+ solution as a function of the applied potential (left). Cyclic voltammogram and corresponding changes in absorbance recorded at 521 nm (right). For simplicity, only the part of the potential scan (the reduction process from −0.4 to −1.4 V and back) is shown. Photoreduction of NAD+ as a

Molecular ordering at electrified interfaces: Template and potential effects

• Thanh Hai Phan and
• Klaus Wandelt

Beilstein J. Org. Chem. 2014, 10, 2243–2254, doi:10.3762/bjoc.10.233

• adsorption and phase transition of 1,1’-dibenzyl-4,4’-bipyridinium molecules (abbreviated as DBV2+) on a chloride-modified Cu(111) electrode surface. The cyclic voltammogram (CV) of the Cu(111) electrode exposed to a mixture of 10 mM HCl and 0.1 mM DBVCl2 shows three distinguishable pairs of current waves P1

• effects, in the structure formation process of DBV cations on these modified Cu electrode surfaces. Keywords: cyclic voltammogram; scanning tunneling microscopy; self-assembly; template effect; viologen; Introduction The precise control of the self-organization of molecular layers on either conducting

• electrode surface due to their hydrophobic properties [4]. The actual shape of the black cyclic voltammogram in Figure 1, in particular the relative intensities of the various peaks can be understood when considering the involvement of “solution species” and “surface limited” reactions, respectively

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

• Bradley D. Rose,
• Peter J. Santa Maria,
• Aaron G. Fix,
• Chris L. Vonnegut,
• Lev N. Zakharov,
• Sean R. Parkin and
• Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

• -coupling of a variety of trialkylsilylacetylenes to either 9 or 11 were modest to very good (Table 1) but were not optimized. Optical and electronic properties. Shown in Figure 2 are the UV–vis spectrum and the cyclic voltammogram of 8c, data that are representative of all the 5,11-diethynyl-IF-diones. As

• [1,2-b]fluorenes and related indeno[1,2-b]fluorene-6,12-diones. UV–vis spectrum (left) and cyclic voltammogram (right) of dione 8c. Kohn–Sham HOMO (left) and LUMO (right) plots of 8a. Views perpendicular to the average plane of the π stack. 1st row left to right – 8a, 8b, 8c; 2nd row – 8d, 8d, 8e; 3rd

The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

• Sarah Bay,
• Gamall Makhloufi,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

• disordered water molecules were omitted for clarity) and the intra- and intermolecular π–π-stacking interactions between an inversion symmetry related pair (right, hydrogen atoms were omitted for clarity). Cyclic voltammogram of dyad 8c (recorded in CH2Cl2, T = 298 K, c (8c) = 0.1 mol·L−1, Pt working

Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ³,2-benziodaoxol-3-one

• Nico Santschi,
• Roman C. Sarott,
• Elisabeth Otth,
• Reinhard Kissner and
• Antonio Togni

Beilstein J. Org. Chem. 2014, 10, 1–6, doi:10.3762/bjoc.10.1

• and a Ag/Ag+ (0.1 M AgBF4 in MeCN) reference electrode were employed with a scan rate of 0.1 V/s. Analysis of the resulting cyclic voltammogram of a 1 mM solution of 3 revealed three quasi-reversible processes with cathodic peak potentials (Epc) of −1.2, −1.7 and −1.8 V, respectively (Figure 5

Stability of SG1 nitroxide towards unprotected sugar and lithium salts: a preamble to cellulose modification by nitroxide-mediated graft polymerization

• Guillaume Moreira,
• Laurence Charles,
• Mohamed Major,
• Florence Vacandio,
• Yohann Guillaneuf,
• Catherine Lefay and
• Didier Gigmes

Beilstein J. Org. Chem. 2013, 9, 1589–1600, doi:10.3762/bjoc.9.181

• . However, Bagryanskaya et al. [35] proved that the hydroxylamine derivative from SG1 is unstable. The cyclic voltammogram of SG1 also proved the instability of the SG1 oxoammonium cation since its reversible reduction is not observed (Figure 10). In conclusion, the degradation of SG1 in DMA/LiCl solutions

Hybrid super electron donors – preparation and reactivity

• Jean Garnier,
• Douglas W. Thomson,
• Shengze Zhou,
• Phillip I. Jolly,
• Leonard E. A. Berlouis and
• John A. Murphy

Beilstein J. Org. Chem. 2012, 8, 994–1002, doi:10.3762/bjoc.8.112

• determined. The 1H NMR spectrum showed the characteristic upfield shift of proton signals for nonaromatic electron-rich donors. Figure 2 shows the cyclic voltammogram of 21 (blue trace) and a comparison with 8 (X = PF6) (red trace). As seen, 21 undergoes reversible redox chemistry [E1½ (DMF) = −1.75 V, E2

• ½ (DMF) = −1.63 V versus Fc/Fc+; this corresponds to E1½ (DMF) = −1.30 V, E2½ (DMF) = −1.18 V versus SCE]. The cyclic voltammogram, together with the NMR determination above, shows that 11 is a stable imidazole-derived donor (i.e., it does not decompose under the conditions used for its formation) [15

Thiophene-based donor–acceptor co-oligomers by copper-catalyzed 1,3-dipolar cycloaddition

• Stefanie Potratz,
• Amaresh Mishra and
• Peter Bäuerle

Beilstein J. Org. Chem. 2012, 8, 683–692, doi:10.3762/bjoc.8.76

• energy level diagram for thiophene–triazole co-oligomers 5, 6, 10–14. Cyclic voltammogram of bithienyl-triazole 14 in dichloromethane/TBAPF6 (0.1 M) versus Fc/Fc+ at 100 mV s−1 (red: monomer 14, gray: during polymerization, blue: polymer film). Synthesis of 3-azidothiophene 2. One-pot, two-step procedure

Self-assembly of Ru₄ and Ru₈ assemblies by coordination using organometallic Ru(II)₂ precursors: Synthesis, characterization and properties

• Sankarasekaran Shanmugaraju,
• Dipak Samanta and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2012, 8, 313–322, doi:10.3762/bjoc.8.34

• (2a–2c) recorded in CH3CN at 298 K, and cyclic voltammogram of 2c (right) performed in CH2Cl2/0.1 M (n-Bu)4NPF6 with a scan rate of 100 mV s−1 versus SCE at 298 K. Possible octanuclear prism and tetranuclear macrocycle resulting from the combination of a tetradendate donor with a clip-type acceptor

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• ). Characterisation of physical properties A film of methyl-capped dimethylaminosexithiophene 1b on ITO glass was obtained by spin coating from a chloroform solution, and the redox properties were compared to those of nonfunctionalised analogue 2b (Figure 2; Table 1). In the positive scan, the cyclic voltammogram for

Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine

• Jean Garnier,
• Alan R. Kennedy,
• Leonard E. A. Berlouis,
• Andrew T. Turner and
• John A. Murphy

Beilstein J. Org. Chem. 2010, 6, No. 73, doi:10.3762/bjoc.6.73

• , these two donors can also cleave appropriate arenesulfonamides [25], aryl alkyl sulfones [25][26], Weinreb amides [28] and acyloin derivatives [29]. They are also prone to transfer two electrons rather than one, with the cyclic voltammogram (c.v.) of 8 showing a single 2-electron reversible redox wave

Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

• Adam W. Franz,
• Svetlana Stoycheva,
• Michael Himmelhaus and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72

• thioacetate. Due to unsymmetrical substitution, the dyad 2c showed two distinctly separated, reversible oxidations at E00/+1 = 668 mV and E0+1/+2 = 853 mV. The cyclic voltammogram of the triad 2d displayed three distinctly separated, reversible oxidations at E00/+1 = 608 mV, E0+1/+2 = 765 mV, and E0+2/+3

• refractive index of 1.490 at 500 nm, which resulted from a study on biphenylthiolates on gold in excellent agreement with theory [63]. Normalized absorption (solid line) and emission (dashed line) spectra of thioacetate 2d (recorded in dichloromethane, T = 298 K). Cyclic voltammogram of thioacetate 2d

A convenient method for preparing rigid-core ionic liquid crystals

• Julien Fouchet,
• Laurent Douce,
• Benoît Heinrich,
• Richard Welter and
• Alain Louati

Beilstein J. Org. Chem. 2009, 5, No. 51, doi:10.3762/bjoc.5.51

• : 1a (I−); circles: 1b (BF4−); up triangles: 1c (PF6−); down triangles: 1d (CF3SO3−). Cyclic voltammogram of 1a in CH3CN (0.1 M NBu4PF6): (i), (ii) cathodic and anodic range of the voltage scan. Scan rate 100 mV·s−1. The black star denotes the initial and final potential. 1-[4-(dodecyloxy)phenyl]-3