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

• well known that the hydrogen atom at the C2 carbon atom of the imidazole core is more acidic as those in the C4/C5-position, where the methyl groups are expected to also have a significant effect on the molecular interactions. Platinum complexes using the 4,5-dimethylimidazole motif as a ligand were

• ). The setup consisted of a glassy carbon working electrode, a platinum wire counter electrode and a silver wire as reference electrode. The cutoff at which the cathodic limit Ered and the anodic limit Eox were determined was −0.1 and 0.1 mA cm−2. The electro-chemical window EEW is determined from the

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

• Yong-Chang Zhai,
• Shimon Oiwa,
• Shinobu Aoyagi,
• Shohei Ohno,
• Tsubasa Mikie,
• Jun-Zhuo Wang,
• Hirofumi Amada,
• Koki Yamanaka,
• Kazuhira Miwa,
• Naoyuki Imai,
• Takeshi Igarashi,
• Itaru Osaka and
• Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

• supporting electrolyte at 25 °C with a scan rate of 0.05 V/s, for C60 (blue), t-Bu-FIDO (red), and t-Bu-FIDS (black). Glassy carbon, platinum wire, and Ag/Ag+ electrodes were used as the working, counter, and reference electrodes, respectively. J–V curves of BHJ OPV devices. (a) ITO/ZnO/fullerene:P3HT (1:1

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

• Masahiro Kako,
• Masato Kai,
• Masanori Yasui,
• Michio Yamada,
• Yutaka Maeda and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100

• on a BAS CV50W electrochemical analyzer (BAS Inc.). The reference electrode was a saturated calomel reference electrode (SCE). The glassy carbon electrode was used as the working electrode, and a platinum wire was used as the counter electrode. All potentials are referenced to the ferrocene

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• 1–3 mg of sample in a 100 μL platinum pan (under nitrogen). The data was analyzed on Universal Analysis 2000 4.4A software. Synthetic procedures to access dicyanopyrazinoquinoxalines (DCPQs) 1a–6a Pyrazino[2,3-b]quinoxaline-2,3-dicarbonitrile (1a) To a 50 mL round-bottom flask was added DDQ (0.581 g

Advancements in hydrochlorination of alkenes

• Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

• functional group tolerance. Yang reported a hydrochlorination promoted by visible light over platinum, gold, and palladium supported on zirconia [74]. The reaction demonstrated moderate efficiency, yielding an 85:15 mixture of products 100 and 126 with low conversion (Scheme 20). The use of hydrochloric acid

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• clinical trials for the treatment of non-small-cell lung cancer and platinum-resistant ovarian cancer, but was halted in phase II due to dose-limiting peripheral neuropathy and limited efficacy in vivo [80]. However, this family of depsipeptides remains of therapeutic significance and has recently been

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

• terpyridine-bearing platinum–salphen known for their luminescence properties [41]. The closing process of the tweezers 12 was studied by NMR or UV–vis titrations with Zn2+ and other cations such as Pb2+, Fe2+, Cu2+, Eu3+, and Yb3+ indicating in all cases a 1:1 association model. The system can then be

• . Vives and co-workers reported bis(platinum–salphen)terpyridine tweezers 20 that can intercalate in the U form extended aromatic guests such as coronene and perylene [52]. The opening of the tweezers with the addition of Zn2+ released the guest demonstrating an example of negative allosteric regulation

• such Pt(II) dissymmetric tweezers could be controlled as aryl thioethers are more labile than alkyl thioethers. The addition of Cl− thus first breaks the Pt–SAr bond. Platinum-based dissymmetric tweezers were also synthetized using NHC thioether ligands that are more stable than the phosphine thioether

Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

• Ruichen Lan,
• Brock Yager,
• Yoonsun Jee,
• Cynthia S. Day and
• Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

• molecule of amine delivers a proton to the alkylgold intermediate (for protodeauration). In a platinum-catalyzed hydroamination, a protodemetalation pathway is supported by kinetics and reactivity studies on generated platinum alkyl intermediates [46]. In a palladium-catalyzed hydroamination, a

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

• Nataliia V. Kirij,
• Andrey A. Filatov,
• Yurii L. Yagupolskii,
• Sheng Peng and
• Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

• defluorosilylation product was obtained [11]. In a related study of the hydrosilylation reaction of olefins 1a,b, it was shown that, depending on the catalyst used, platinum or rhodium compounds, along with the products of the addition of silane to the double bond, the elimination of the fluorine atom occurs with

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

• naphthyl substituents carrying each an alkyne moiety on the ortho position. Ring expansion of both thiophene units in 19 was then triggered by platinum catalysis to generate the corresponding thiopyrans, and finally the bromine atoms located on the latter rings were exploited for the ring closure of the

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• platinum disk (diameter = 1.6 mm) or a glassy carbon disk (3 mm) was used as the working electrode. The reference electrode was separated from the solution containing the substrate by a ceramic frit. Measured potentials were referenced to ferrocene/ferrocenium (Fc/Fc+) redox couple, measured before and

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

• as a quasireference electrode, while a platinum wire served as a counter electrode to facilitate the redox reactions. For calibration purposes, the potentials were standardized using the standard ferrocene/ferrocenium (Fc/Fc+) redox system, a well-known and widely used reference for establishing

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

• compete with classic phosphorescent emitters that employ scarce metals such as iridium and platinum [7][8][9]. Since its first report in 2012 by Uoyama et al., 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) has been a benchmark TADF emitter due to its high quantum yields and excellent

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

• NADH-analogues are the subject of most studies for recycling sacrificial donors. NADH has been electrochemically recycled but a careful control of pH is required to prevent dimerization reactions [44][45]. For example, Glusac and co-workers recycled BIH and acridine analogues using platinum electrodes

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

• -purged saturated solutions containing 0.10 M Bu4NPF6 as a supporting electrolyte, a platinum electrode as counter electrode, a glassy carbon electrode as working electrode, and the Ag/AgNO3 (0.1 M in ACN) couple as the reference electrode. Ferrocenium/ferrocene (Fc+/Fc) redox couple was used as an

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

• 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

• 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

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• (Bruker Optik GmbH, Ettlingen, Germany), equipped with an ATR (single-reflection Platinum diamond attenuated total reflectance) system. The following FTIR conditions were set up: acquisition range 4000–400 cm−1, resolution 4 cm−1, number of scans 128, sample mass 10–20 mg, spectrum range for the DLaTGS

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

• Julian Spils,
• Thomas Wirth and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 27–32, doi:10.3762/bjoc.19.2

• oxidation of iodoarenes to form DIS by Wirth et al. (Scheme 1B) [39]. Herein, established conditions for synthesizing DIS were transferred into flow chemistry utilizing a model flow reactor with two platinum electrodes. Other recent examples include the generation of five-membered CDIS utilizing fluorinated

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

• electrochemical workstation (CHI instruments, Inc., Shanghai, China) using N2-purged saturated solutions (NI-PTZ, NI-PTZ2, NI-Ph-PTZ, and NI-PhMe2-PTZ in deaerated dichloromethane, NI-PTZ-O in deaerated acetonitrile) containing 0.10 M Bu4NPF6 as a supporting electrolyte, a platinum electrode as counter electrode

• with gauze platinum as working electrode, a platinum wire as counter electrode, and Ag/AgNO3 as reference electrode. Bu4N[PF6] was used as the supporting electrolyte. The potential was regulated with a CHI610D electrochemical workstation (CHI instruments, Inc., Shanghai, China), and the spectra were

Electrochemical formal homocoupling of sec-alcohols

• Kosuke Yamamoto,
• Kazuhisa Arita,
• Masashi Shiota,
• Masami Kuriyama and
• Osamu Onomura

Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

• -1,2-diols through the formal homocoupling of sec-alcohols using platinum electrodes in an undivided cell (Scheme 1c). Results and Discussion We commenced the optimization study for the electrochemical formal homocoupling of sec-alcohols by using 1-phenylethanol (1a) as a model substrate. The results

• are summarized in Table 1. The electrolysis was carried out using an undivided cell in the presence of Et4NBr as an electrolyte with a mixed solvent of MeCN and H2O under air atmosphere. When 4 F/mol of electricity was passed through the reaction mixture using two platinum electrodes at 0 ºC, the

• . The present reaction smoothly proceeded in a simple undivided cell with platinum electrodes under constant current conditions, affording pinacol-type products in moderate to good yields with good to high diastereoselectivities. The successful large-scale experiment showed the potential synthetic

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

• relevant heterocycles. From vinyl acetates to α-azidoketones. Substrate scope. Reaction conditions: α-arylvinyl acetate (0.5 mmol), TMSN3 (1.0 mmol), n-Bu4NPF6 (0.5 mmol), H2O (2.5 mmol), MeCN (5 mL), carbon cloth anode, platinum cathode, undivided cell, Ecell = 2.3 V, room temperature, 6 h. a2 h

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

• ) was placed in the cathodic chamber of a divided cell (40 mL beaker, 3 cm diameter, 6 cm height) equipped with a platinum cathode (5 × 5 cm2), a platinum anode (2 × 1 cm2), and a ceramic cylindrical diaphragm (1.5 cm diameter). A 0.3 M solution of Bu4NClO4 in DMF (4 mL) was placed in the anodic chamber

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

• 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