Electrochemical synthesis of cyclic biaryl λ³-bromanes from 2,2’-dibromobiphenyls

• Andrejs Savkins and
• Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

• to 2.88 V) and unsuccessful substrates 4i–m, S9a, S9b (from 1.73 V to 2.54 V) (Table S2 in Supporting Information File 1) span similar potential regimes suggesting that the success of the anodic oxidation likely depends on the structural rather than the electrochemical properties of the starting 2,2

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• and separation technology [3][4][5][6][7][8]. Conversely, porphyrins are connected via methine (=CH-) bridges, resulting in an 18 π-electron macrocyclic system affording macrocyclic planarity as well as unique photophysical and electrochemical properties (Figure 1b). While corroles share similarities

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• ) on it, besides it has a thick ring structure. The electrochemical properties of the modified CD-based conjugative polymers have been intensively studied by Terao and co-workers [83]. Apart from a typical CD-based polyrotaxane network, which contains CDs and linear polymer chain-based polyrotaxane as

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• structural features of violanthrones suggest that these materials may possess similar charge transport, optical and electrochemical properties to those of PDIs. However, the larger π-conjugated system of violanthrone, along with the two carbonyl groups, increases the possibility of stronger π–π

• frontier orbitals. Electrochemical studies The electrochemical properties of the dyes were investigated by square wave voltammetry (SWV) and cyclic voltammetry (CV) and the data are summarised in Table 1, with the plots shown in Figure 6. All the materials exhibit at least one reversible reduction and two

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• possibility of alkylation of the nitrogen atom in the heterocycle cannot be excluded. This alternative pathway is similar to the previously described interaction of the aforementioned catechol with 3,5-dimethylpyrazole or benzimidazole [55]. A study of the structure, electrochemical properties, anti

• neighbouring group O2–H2, and there is no intramolecular hydrogen bond between hydroxy groups in molecule 8 (Figure 2(b)). A π-stalking was found between the pyridine groups in molecules belonging to the neighbouring pairs with the corresponding distance of 3.45(1) Å. Electrochemical properties The study of

• the electrochemical properties of functionalized catechols allows one to suggest the mechanism of their electrooxidation, establish electron transfer centers, and predict antioxidant activity based on electrochemical data. To determine electron-transfer centers, the oxidation potentials of the

Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

• Marwa Elsbaey,
• Naoya Oku,
• Mohamed S. A. Abdel-Mottaleb and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

• , copolymerized β-alkylpyrroles are among the most investigated organic materials for their enhanced physical and electrochemical properties [4][5]. Accordingly, chemists have focused on developing selective synthetic strategies for the construction of β-alkylpyrroles [1]. While the pyrrole nucleus is featured in

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

• Siham Asyiqin Shafie,
• Ryo Nozawa,
• Hideaki Takano and
• Hiroshi Shinokubo

Beilstein J. Org. Chem. 2024, 20, 1967–1972, doi:10.3762/bjoc.20.172

• radicals derived from azo radical initiators. The radical selectively attacked the distal α-position relative to the meso-position to construct a nonaromatic bowl-shaped structure. The photophysical and electrochemical properties of the obtained radical adducts were compared to those of the parent Ni(II

• 2a obtained by TD DFT calculations at the M06/6-31G(d)+SDD//B3LYP-D3/6-31G(d)+SDD level of theory was consistent with the experimental results. Therein, the absorption band at 670 nm (f = 0.0026) was attributed to the transition from HOMO to LUMO+1. Next, the electrochemical properties of 2a in

• exhibited markedly different photophysical and electrochemical properties with norcorrole 1. The intrinsic reactivities of Ni(II) norcorroles with neutral radical species were revealed by DFT calculations, where populations of the HOMO of the norcorrole unit and the spin density of the radical intermediate

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)

• Hiwot M. Tiruye,
• Solon Economopoulos and
• Kåre B. Jørgensen

Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153

• their highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels can be derived via the oxidation onset potentials as shown in the literature [51]. The electrochemical properties of all products are summarized in Table 5. Individual CVs, with onset potentials

• of 1-chrysenol (3b) at different electron equivalents.a Anodic methoxylation of PAPs followed by hydrolysis in two separate steps.a Synthesis of o- and p-quinones without isolation of the acetal intermediate.a Electrochemical properties of PAPs. Supporting Information Supporting Information File 6

Synthesis and physical properties of tunable aryl alkyl ionic liquids based on 1-aryl-4,5-dimethylimidazolium cations

• Stefan Fritsch and
• Thomas Strassner

Beilstein J. Org. Chem. 2024, 20, 1278–1285, doi:10.3762/bjoc.20.110

• lead to a decreasing conductivity, with the difference between butyl and octyl being more drastic than the difference between octyl and dodecyl. To determine the electrochemical stability of the TAAILs, their electrochemical properties were investigated using linear sweep voltammetry (LSV, Figure 4

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

• [4]pyrroles [73]. The electrochemical properties of the host–guest system are modulated by a thermally induced electron transfer (ET) that generates the charge separation state [PrS-TTF-C4P•+/Li+@C60•−]. This behavior was first reported with Cl− as an allosteric regulator but was then described with

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• reaction products as 12H-quinoxaline[2,3-b]phenoxazines was confirmed through DFT calculations, X-ray crystallography, and NMR spectroscopy. Electronic absorption spectra (Table 2 and Figures 5–7) and electrochemical properties (Table 3) of the heteropentacyclic compounds 4a–h, 5a–c, 6a,b, and 10c revealed

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• groups representing (a) isopropyl and (b) sec-butyl, were successfully obtained in 84% and 61% yields, respectively. The incorporation of a biphenylene group into the azaacene structure did not result in any significant impact on the electrochemical properties. The electrochemical analysis revealed the

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• derivatives 6–9. Their 5% weight loss temperatures (Td) ranged from 433 to 493 °C (Figure 5a and Table 1). Electrochemical properties The electrochemical properties of compounds 6–9 were studied by cyclic voltammetry (CV) selecting the electrochemical window from −1.6 to 1.7 V and the CV data were corrected

• electrochemical potential scales. The CV technique provided detailed cyclic voltammograms, allowing us to analyze the redox behavior and electrochemical properties of the compounds under investigation. Chemical structures of pyridine-3,5-dicarbonitrile-based TADF emitters. Absorption (a, b) and PL (c, d) spectra

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

• )-based catalyst and its employment in photo-driven CO2 reduction. The cobalt core was hexacoordinated by two chelating quinolyl-triazole ligands and two −NCS groups. The electrochemical properties suggested that this complex could reduce carbon dioxide. The photocatalytic system chosen for this target

• . Proposed mechanism for the photoinduced reduction of carbon dioxide with the system presented in this work. Optical and electrochemical properties of complex 1 in DMA. Selectivity study of photocatalytic CO2 reduction with complex 1 as the catalyst.a Photocatalytic CO2 reduction tests with different

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• emissive nanoaggregates in a THF/H2O mixture. Altering the substituents proved as an effective approach to tune the electrochemical properties of the compounds, resulting in comparable LUMO energy levels. The products therefore hold potential as solid-state emitters and n-type materials for organic

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

• films using ethyl acetate as the solvent. The optoelectronic properties were assessed for both solution and film, and the electrochemical properties were probed in solution. To validate the potential as electron transporting layers, each film was used in conventional OPVs as the CIL with processing from

• are reported for the design strategy used, their synthesis, optoelectronic properties, electrochemical properties, and processability from ethyl acetate for thin film formation. Lastly, each new CIL material was tested in conventional OPVs by processing with ethyl acetate, a green solvent [20][21][22

• considered green, where a green solvent can be described as one that exhibits little to no toxicity to humans or animals, and has a minimal environmental impact when considering life-cycle assessments [21]. In terms of the electrochemical properties of the series, it was hypothesized that the addition of a

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

• 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

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

• sodium polyphosphides. Further reaction of sodium 3,4,5-tris(3-chlorophenyl)-1,2-diphosphacyclopentadienide with [FeCp(η6-C6H5CH3)][PF6] complex gives a new 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene. The electrochemical properties of 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene were studied

• ; electrochemical properties; phosphacyclopentadienide anion; phosphaferrocene; phosphonium salt; phosphorus heterocycle; Introduction Among the various heterometallocenes reported to date, phosphaferrocenes are by far the most investigated because of their structural and electronic features [1][2] and remain the

• electrochemical properties. Results and Discussion Synthesis of tris(chlorophenyl)cyclopropenyl bromides and derivatives Cyclopropenium (cyclopropenylium) ions have always attracted attention of the synthetic chemists because of the unique combination of stability and reactivity [38][39][40]. The synthesis of

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

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• the potential applications in optoelectronic devices [1][2][3][4], solid-phase sensing [5], bioimaging [6][7], security [8], and storage devices [9]. The optical and electrochemical properties of the organic emitters can be tuned by external stimuli, such as mechanical force, heat, solvent, acid and

• solution and in the solid state and with multicolor tunability by external stimuli are crucial for task-specific applications. Recently, donor–acceptor (D–A)-based organic emitters have shown tunable optical and electrochemical properties due to alteration of the intermolecular charge-transfer (ICT

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

• . Five rhenium complexes with 1,2,3-triazoloquinoxalines and a novel TIQ rhenium complex were synthesized, and their structures were confirmed via X-ray crystallography. All complexes were characterized and compared regarding their absorption and electrochemical properties. The TIQ complex could be

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

• dyes [10][11][12][13][21][22][27][28][32]. In our previous work [33], we have reported the synthesis, optical and electrochemical properties of the (D–π)2Ph-type fluorescent dye OTK-2 with two (diphenylamino)carbazole-thiophene units as D–π moiety connected through a phenyl ring (Scheme 1). The ICT

• the two dyes: OTK-2 has a cross-conjugated system due to the involvement of the 1,3-phenylene unit as an additional linker, but OTT-2 has a conjugated system. Therefore, it is interesting to reveal the optical and electrochemical properties of (D–π)2-type fluorescent dyes, making a comparison with (D

Electrochemical and spectroscopic properties of twisted dibenzo[g,p]chrysene derivatives

• Tomoya Imai,
• Ryuhei Akasaka,
• Naruhiro Yoshida,
• Toru Amaya and
• Tetsuo Iwasawa

Beilstein J. Org. Chem. 2022, 18, 963–971, doi:10.3762/bjoc.18.96

• torsion angles on the chemical properties would be beneficial in terms of creating DBC-based materials. Results and Discussion Electrochemical properties Cyclic voltammograms (CVs) and square-wave voltammograms (SWVs) were measured for DBC-H, DBC-Me, DBC-SMe, DBC-Br, DBC-S(O)2Me, and DBC-Si (Figure 2) [53

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• annulene [12], and twisted naphthalene as central spacers [19]. As its close analogue, selenophene has properties very similar to those of thiophene. Fused aromatic compounds containing selenophene units show favorable optical and electrochemical properties and improved charge transport characteristics in