Enhanced host–guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges

• Eiichi Kayahara,
• Yoshiyuki Mizuhata and
• Shigeru Yamago

Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38

• a 1,2-dichloroethane solution of a sample containing 0.10 mol L−1 Bu4N+ B(C6F5)4−. The cyclic voltammogram of the complex showed one reversible oxidation wave of [10]CPP at 0.92 V versus (vs) ferrocene/ferrocenium couple (Fc/Fc+) (Figure 3a), which was positively shifted by 0.13 V from that of

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• 2020 American Chemical Society. This content is not subject to CC BY 4.0. Cyclic voltammogram of dinaphthooxepine 33, evidencing the irreversibility of the reduction process during the first cycle, leading to the formation of PBI 6f upon redox-triggered O-extrusion. Reprinted with permission from [66

Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

• Kazuhiro Okamoto,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2024, 20, 264–271, doi:10.3762/bjoc.20.27

• cyclic voltammogram of 1. (B) Cyclic voltammograms of 1 in the presence of additives (AcOH or HFIP). (C) Comparison of oxidation potentials of 1 using Bu4NOAc or Bu4NCl. (D) Cyclic voltammograms for the cathodic side. All cyclic voltammograms were recorded in CH2Cl2/Bu4NPF6 (0.1 M). Sample concentration

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• ), respectively. A more intense current arises with the third redox process occurring at −2.52 V, which could be assigned to the reduction localized on the ligand (compare with the cyclic voltammogram in Supporting Information File 1, Figure S8). We investigated the electrochemical properties also under a CO2

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• illumination). a) DSC and TGA thermograms measured at a heating rate of 10 °C min−1 under N2 flow. b) Cyclic voltammogram (CV) and differential pulse voltammogram (DPV) analyzed in dry CH2Cl2 at a scan rate of 50 mV s−1 under an argon atmosphere (insert: HOMO/HOMO−1/LUMO orbitals). a) Schematic structure of

Organic thermally activated delayed fluorescence material with strained benzoguanidine donor

• Alexander C. Brannan,
• Elvie F. P. Beaumont,
• Nguyen Le Phuoc,
• George F. S. Whitehead,
• Mikko Linnolahti and
• Alexander S. Romanov

Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95

• ) possible isomers for 4BGIPN material. Ellipsoids are shown at the 50% level where hydrogen atoms are omitted for clarity. Full range cyclic voltammogram for 4BGIPN. Recorded using a glassy carbon electrode in THF solution (1.4 mM) with [n-Bu4N]PF6 as supporting electrolyte (0.13 M), scan rate 0.1 Vs−1. UV

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes

• Almaz A. Zagidullin,
• Farida F. Akhmatkhanova,
• Mikhail N. Khrizanforov,
• Robert R. Fayzullin,
• Tatiana P. Gerasimova,
• Ilya A. Bezkishko and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139

• complex). Potentials vs Ag/AgCl. Scan rate = 100 mV⋅s−1, room temperature. Cyclic voltammogram of 8c republished with permission of Royal Society of Chemistry from [37] (“Synthesis, structure and electrochemical properties of 3,4,5-triaryl-1,2-diphosphaferocenes” by I. A. Bezkishko et al., Inorg. Chem

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• solution and in the solid state. Cyclic voltammogram for EtH-T-DI-DTT (1), at a scan rate of 0.1 V s−1 using a Pt disk as the working electrode, Pt wire as the counter electrode, and Ag wire as the quasi-reference electrode in ca. 0.1 mM of the compound in CH2Cl2 with TBAPF6 (0.1 M) as the electrolyte [64

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• (C6F5)3), which were consistent with the theoretical calculation results. Yang and co-workers compared the energy level distributions of the HOMO and LUMO of CzPA-F-PD (compound 7 in Figure 5) before and after protonation, which were diverse [32]. The cyclic voltammogram (CV) curves of CzPA-F-PD and

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

• 4f. Calculated energy levels for compounds 4a–d and their spatial distribution of the HOMO–LUMO frontier molecular orbitals from DFT calculations. Visualization of MEP for compounds 4a–d calculated by B3LYP method with 6-31G(d) basis set. Cyclic voltammogram for 4c in 0.1 M (n-Bu)4NBF4/acetonitrile

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

• rotaxane 1a (top) and thread 4a (bottom) in CDCl3 (a designation of the signals is described in Figure 2). 1H,1H-ROESY NMR spectrum (600 MHz) of the rotaxane 1a in CDCl3. Cyclic voltammogram of ferrocene rotaxane 1a (0.67 mM) in CH2Cl2/CH3CN 1:5 (TBAPF6 0.10 M, scan rate = 10 mV/s). Single crystal X-ray

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

• [29]. DSC curves of compounds 4 and 5. Absorption and PL spectra (λex = 330 nm) of compounds 3–6. a) Absorption spectra as neat films, dilute THF and toluene solutions. b) PL and phosphorescence spectra in dilute THF solutions at 77 K. a) Cyclic voltammogram of derivative 3 in dichloromethane (a three

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

• solution (10−5 M). Inset: photograph of a CH2Cl2 solution of 1. (b) Cyclic voltammogram of 1 (0.1 M n-Bu4NPF6 in DCM) at a scan rate of 50 mV s−1. Molecular orbitals of peropyrene derivative 6 and the dicyclopenta-fused peropyrene 1. Chemical structures of dicyclopenta-fused pyrene derivatives i–iii

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

• 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

• chloromethyl radical can be formed with photoredox catalysis from monochloroacetic acid, but we were not yet able to apply such reactions in a productive manner, such as in cyclopropanation reactions. A part of the industry around monochloroacetic acid. Cyclic voltammogram of monochloroacetic acid and

Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

• Celine Bittner,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2019, 15, 2534–2543, doi:10.3762/bjoc.15.246

• displacement parameters drawn at 50% probability; hydrogen atoms are omitted for clarity. Selected bond lengths [Å] and angles [°]: Fe–Ct1 1.6558(2), Fe–Ct11 1.6548(2), Ct1–Fe–Ct11 176.83(2), C10–C20 1.198(3), C9–C10–C20 177.6(2), C10–C20–C19 179.1(2). Cyclic voltammogram of 2a in DCM, 0.2 M n-Bu4NPF6, 1 V s−1

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• redox properties of phthalimide-bearing O6-corona[3]arene[3]tetrazines, a cyclic voltammogram (CV) and a differential pulse voltammogram of 3a were recorded. As depicted in Figure 3, macrocycle 3a undergoes a reversible sequential one-electron redox process at −811, −883, −1871, and −2367 mV. The

N-Arylphenothiazines as strong donors for photoredox catalysis – pushing the frontiers of nucleophilic addition of alcohols to alkenes

• Fabienne Speck,
• David Rombach and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 52–59, doi:10.3762/bjoc.15.5

• process of 1 is almost reversible but induces to some extent an irreversible oxidation process that shows up as further reduction half wave in the cyclic voltammogram. This is true for almost all synthesized derivatives 3–9. The radical dication is known to undergo disproportionation reactions [27], which

• phenothiazines 1–11 as potential photoredox catalysts. Normalized UV–vis absorption spectra above 290 nm of N-phenylphenothiazines 1–11 (left) and representative cyclic voltammogram of 2 (right). Proposed mechanism for the photoredox-catalyzed addition of methanol to α-methylstyrene (13a). (ET = electron

Oxidative and reductive cyclization in stiff dithienylethenes

• Michael Kleinwächter,
• Ellen Teichmann,
• Lutz Grubert,
• Martin Herder and
• Stefan Hecht

Beilstein J. Org. Chem. 2018, 14, 2812–2821, doi:10.3762/bjoc.14.259

• = 5∙10−4 M, dE/dt = 1 V s−1. Cyclic voltammogram of DTE-PhFluorene. The ring-closed isomer (red dashed line) is formed both under a) reductive and b) oxidative conditions from O-DTE-PhFluorene (blue line), as shown by the emerging characteristic oxidation and reduction waves, respectively. Experiments

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

• Hendrik V. Schröder and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

• and operation of the electro- and photochemically switchable rotaxane 18 which acts as potential memory device. (a) The redox-switchable rotaxane 19 with a donor–acceptor pair which is stable in five different switching states. (b) Cyclic voltammogram showing the transitions between the five oxidation

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

• /b, 16a/b and 18a/b supports this assumption. The cyclic voltammogram of 18a/b shows an oxidation peak at 1.75 V to 1.85 V (Figure 3). In the cyclic voltammogram of malonic acid derivative 16a/b a peak appears at a potential of 2.4 V (Figure 3). The malonic acid derivative 15a/b does not show any

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