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

• Supporting Information File 1). The redox properties of 1 were investigated using cyclic voltammetry in a DMA solution with 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF6) as the supporting electrolyte (Table 1). The concentration of the analyte was 5 mM. Only the cathodic scan resulted in a rich

• -centered d–d transitions. Cyclic voltammetry of complex 1 in 0.1 M TBAPF6 solution of (a) DMA and (b) DMA/TEOA 5:1 (v/v). Black curves are registered under Ar and red curves are recorded under CO2 atmosphere. A glassy-carbon disk was used as the working electrode and the internal references used are (a

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

• optoelectronic devices. The electrochemical behavior of TPECNz was analyzed by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) in CH2Cl2 containing 0.1 M n-Bu4NPF6 as a supporting electrolyte. As illustrated in Figure 5b, the molecule shows multiple quasi-reversible oxidation and reduction

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• crystallographically characterized. Electrochemistry The 1+, 1H, and 12 species were investigated using cyclic voltammetry in THF/0.1 M Bu4NPF6 at a scan rate of 50 mV s−1. The voltammograms (shown for one series of compounds in Figure 6) were qualitatively similar to those reported and shown elsewhere for other

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• with trifluoroacetic acid (TFA) resulted in a cationic 40-H+. Cyclic voltammetry and differential pulse voltammetry were performed to investigate the electrochemical properties of 40-H+. The cation exhibited two reversible oxidations and two to three reductions. The redox potentials were influenced by

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• properties of the four CILs were probed using solution cyclic voltammetry (CV; Figure 4) and differential pulse voltammetry (DPV; Supporting Information File 1, Figures S27–S30), using dichloromethane as the solvent. For all reversible reduction or oxidation waves, HOMO and LUMO energy levels were determined

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• first thiolation and intramolecular cyclization of propargyl azides the removal of N2 and a proton. Subsequently, monothiolated perroles were subjected to the second thiolation process to prepare 3,4-bisthiolated pyrroles. Cyclic voltammetry and DFT calculations revealed that the 3,4-bisthiolated

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

• significantly shorter (0.4 Å) than the 3.74(3) Å average distance between nearest neighbor carbazole ligands in 4CzIPN, indicative for much stronger intermolecular interactions. Cyclic voltammetry was used to analyze the redox behavior of 4BGIPN in THF solution containing [n-Bu4N]PF6 as supporting electrolyte

• recorded using a Bruker AVIII HD 500 MHz NMR spectrometer. 1H NMR spectra (500.19 MHz) and 13C{1H} (125.79 MHz) were referenced to dichloromethane-d2 at δ 5.32 (13C, δ 53.84). All electrochemical experiments were performed using an Autolab PGSTAT 302N computer-controlled potentiostat. Cyclic voltammetry

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors

• Grace A. Lowe

Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88

• energy orbitals on photooxidized or photoexcited photosensitizers with more positive potentials. Cyclic voltammetry can be used to measure ground-state redox potentials by varying the potential at a working electrode with respect to a reference electrode and measuring the current response [19]. In

• photocatalysis. Cyclic voltammetry carried out in standard conditions for mimicking an acetonitrile system had not been close enough to the catalytic conditions to get the required redox potentials. The difference between the oxidation potential of a sacrificial donor and the reduction potential of the excited

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• , 130.6, 130.4, 130.3, 123.8, 123.6, 123.1, 116.8, 116.7, 116.5; HRMS–MALDI (m/z): [M + H]+ calcd for C30H17FN2O3S, 505.0944; found, 505.0973. Electrochemical studies The cyclic voltammetry curves were recorded with a CHI610D electrochemical workstation (CHI instruments, Inc., Shanghai, China) in N2

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• -conjugation of 1,8-bis(dimethylamino)naphthalene (DMAN) fragments through a butadiyne linker and a donor–acceptor aryl–C≡C–DMAN conjugation path. The conjugation path can be “switched” simply by protonation of DMAN fragments. X-ray diffraction, UV–vis spectroscopy and cyclic voltammetry are applied to analyze

• us to undertake the current study. X-ray crystallography, UV–vis spectroscopy and cyclic voltammetry were applied to analyze the extent of π-electron conjugation and the efficiency of the particular donor–acceptor conjugation path in chromophores 5. Results and Discussion Synthesis The target

• to its analogs with electron-withdrawing substituents. The redox properties of oligomers 5 were evaluated by cyclic voltammetry (CV) in dichloromethane solution containing 0.1 M n-Bu4NPF6 in the standard three-electrode electrochemical cell: glassy carbon working electrode, platinum auxiliary

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

• Alena V. Dmitrieva,
• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

• cyclic voltammetry time scale. The spin density in the radical anion is mainly localized on the Ni d-orbitals and on the N and O atoms of its coordination environment (see Supporting Information File 1). The reduction of the complex (ΔAlaNi)L7 is irreversible at scan rates lower 2000 mV/s. Full

• complexes. Electrochemical properties For further applications of the (GlyNi)L7 and (ΔAlaNi)L7 complexes in electrochemically activated functionalization of amino acid fragments, a more detailed electrochemical study is an important precondition. Electrochemical properties were investigated using cyclic

• voltammetry (CV) in acetonitrile with 0.1 M Bu4NBF4 as a supporting electrolyte. A platinum disk was used as a working electrode. Formal potential values are given in Table 4. As could be expected, the potential values are rather close to that for the corresponding derivatives of the original ligand L1 [37

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface

• Kendra Drayton-White,
• Siyue Liu,
• Yu-Chia Chang,
• Sakashi Uppal and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156

• on the surface of the electrodes. Supporting Information Supporting Information File 310: Procedures for electrolysis and cyclic voltammetry experiments, characterization of electrolysis products, procedures for synthesis and characterization of electrolysis starting materials. Funding We thank the

Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

• Kaiyue Ye,
• Liyuan Cao,
• Davita M. E. van Raamsdonk,
• Zhijia Wang,
• Jianzhang Zhao,
• Daniel Escudero and
• Denis Jacquemin

Beilstein J. Org. Chem. 2022, 18, 1435–1453, doi:10.3762/bjoc.18.149

• , 138.85, 133.63, 132.71, 132.03, 131.20, 127.35, 126.84, 123.29, 122.89, 116.24, 44.24, 38.01, 30.78, 29.70, 28.71, 24.11, 23.09, 21.19, 10.67; HRMS–MALDI (m/z): [M + H]+ calcd for C40H38N2O2S, 610.2654; found, 610.2649. Electrochemical studies The cyclic voltammetry curves were recorded with a CHI610D

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

• of the Cl atoms in 8b practically did not participate in the frontier orbitals, which explained the similarity of the low-energy range of the experimental spectra. The electrochemical properties of 1,2-diphosphaferrocene 8b were studied by cyclic voltammetry and compared to data for 8c (Table 1 and

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• , and DiKTa-DPA-OMe (DCT = 1.45 Å, 1.81 Å, and 3.34 Å, respectively) reflected in the increased donor strength. The electrochemical properties of DiKTa-OBuIm and DiKTa-DPA-OBuIm were investigated by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) in acetonitrile with 0.1 M tetra-n

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

• Mana Kitano,
• Tsuyoshi Saitoh,
• Shigeru Nishiyama,
• Yasuaki Einaga and
• Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

• addition, 1H NMR and FTIR spectra for the crude compound did not show characteristic peaks derived from carboxylic acid and amide. In order to clarify the role of the anode material, we carried out electrochemical measurements (Figure 1). Cyclic voltammetry was performed using BDD as a working electrode. A

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

• Laura Holzhauer,
• Chloé Liagre,
• Olaf Fuhr,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

• to the triazoloquinoxaline complexes 27a–d. To characterize the electrochemical properties of the obtained complexes, cyclic voltammetry measurements were performed. For complexes 27a–d, irreversible oxidation previously assigned to the Re(I)/Re(II) couple [38][45] can be observed at 1.6 V vs SCE

• confirmed to possess rather different properties than the triazoloquinoxaline complexes in these measurements, including a blue-shift in the absorption spectrum and anodically shifted features in cyclic voltammetry measurements. Abbreviations CuAAC, copper-catalyzed azide–alkyne cycloaddition; DIPEA, N,N

• . Cyclic voltammetry traces for rhenium complexes 27a–d, 29 and 30: 0.5 mM in MeCN solution with 0.1 M Bu4NPF6 under nitrogen at 25 °C, recorded at 0.1 V/s at a glassy carbon electrode and referenced to the saturated calomel electrode (SCE) using Fc/Fc+ as an internal standard (0.46 V vs SCE [12

Synthesis, optical and electrochemical properties of (D–π)₂-type and (D–π)₂Ph-type fluorescent dyes

• Kosuke Takemura,
• Kazuki Ohira,
• Taiki Higashino,
• Keiichi Imato and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

• stannyl D–π unit with 1,3-diiodobenzene, respectively. Their optical and electrochemical properties were investigated by photoabsorption and fluorescence spectroscopy, time-resolved fluorescence spectroscopy, cyclic voltammetry (CV) and molecular orbital (MO) calculations. In toluene the photoabsorption

• –π)2Ph-type fluorescent dyes. Herein, we report the syntheses of (D–π)2-type and (D–π)2Ph-type fluorescent dyes and their optical and electrochemical properties based on photoabsorption and fluorescence spectroscopy, time-resolved fluorescence spectroscopy, cyclic voltammetry (CV) and molecular

• decay measurements were performed on a HORIBA DeltaFlex modular fluorescence lifetime system using a Nano LED pulsed diode excitation source (451 nm). Cyclic voltammetry (CV) curves were recorded in DMF/Bu4NClO4 (0.1 M) solution with a three-electrode system consisting of Ag/Ag+ as the reference

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

• Yi-Lun Li,
• Zhaojiang Shi,
• Tao Shen and
• Ke-Yin Ye

Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103

• (Ecell = 2.3 V, carbon cloth anode, and Pt cathode) of 1-phenylvinyl acetate (1) with azidotrimethylsilane was performed and the desired α-azidoketone (2) was obtained in 68% yield (Table 1, entry 1, for details of the reaction optimization see Supporting Information File 1). The cyclic voltammetry

Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity

• Naoki Kise and
• Toshihiko Sakurai

Beilstein J. Org. Chem. 2022, 18, 956–962, doi:10.3762/bjoc.18.95

• by cyclic voltammetry (Table 3) and acceptors 2 revealed no reduction peaks from 0 to −2.00 V vs SCE [5][6]. Therefore, this electroreductive coupling is initiated by the reduction of compounds 1. There are two possible reaction mechanisms for the reductive coupling of 1 with 2a as illustrated in

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

• wavelength is at 701 nm, which corresponds to 1.77 eV. An ionisation energy of 5.5 eV and an electron affinity of 3.3 eV were estimated by cyclic voltammetry measurements. We have applied this new molecule in organic field effect transistors. The material exhibited a p-type mobility up to 1.33 × 10−4 cm2 V−1

• Cyclic voltammetry (CV) was used to estimate the ionisation energy (IE) and the electron affinity (EA) of the title compound (Figure 9) [63]. CV was measured in a 10−4 M CH2Cl2 solution with 0.1 M tetra-n-butylammonium hexafluorophosphate (TBAPF6) added as electrolyte. A platinum disk electrode, a Pt

Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications

• Sadanobu Iwase,
• Shinsuke Inagi and
• Toshio Fuchigami

Beilstein J. Org. Chem. 2022, 18, 872–880, doi:10.3762/bjoc.18.88

• bromodifluoromethyl phenyl sulfide (1) was measured by cyclic voltammetry in an anhydrous acetonitrile (MeCN) solution containing Bu4NClO4 (0.1 M) using a platinum electrode. One irreversible reduction peak was observed at −2.4 V vs SSCE at a scan rate of 100 mV/s. Even at a much higher scan rate of 500 mV/s, the

• reduction of 1 using o-phthalonitrile as mediator At first, cyclic voltammetry was carried out to investigate the electrocatalytic reduction of bromodifluoromethyl phenyl sulfide (1) with o-phthalonitrile as a mediator. The cyclic voltammograms of o-phthalonitrile in the absence and presence of compound 1

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

• ) Cyclic voltammetry curves of the four compounds and HOMO/LUMO energy level diagram and (d) estimated from the CV tests. Figure 11a–d were reproduced from [45] with permission from The Royal Society of Chemistry. This content is not subject to CC BY 4.0. (a) UV–vis absorbance and (b) PL spectra (excited

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

• Ettore Crovini,
• Zhen Zhang,
• Yu Kusakabe,
• Yongxia Ren,
• Yoshimasa Wada,
• Bilal A. Naqvi,
• Prakhar Sahay,
• Tomas Matulaitis,
• Stefan Diesing,
• Ifor D. W. Samuel,
• Wolfgang Brütting,
• Katsuaki Suzuki,
• Hironori Kaji,
• Stefan Bräse and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

• atoms are omitted for clarity. HOMO, HOMO–1 (H–1), LUMO, and LUMO+1 (L+1) electron density distributions (isovalue: 0.02) and energy levels, excited state energy levels. a) Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) of DICzTRZ in DCM (scan rate = 100 mV/s). b) UV–vis absorption