Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

• Stephanie G. E. Amos,
• Marion Garreau,
• Luca Buzzetti and
• Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

• fragmentation. N-aminopyridinium salts are also emerging starting materials. Iminyl radical generation Hydroxylamines have emerged as key precursors for iminyl radical generation [128]. Their redox properties can be easily tuned through the substitution pattern of the electrophore. They can be subjected to

Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

• Liliia Moshniaha,
• Marika Żyła-Karwowska,
• Joanna Cybińska,
• Piotr J. Chmielewski,
• Ludovic Favereau and
• Marcin Stępień

Beilstein J. Org. Chem. 2020, 16, 895–903, doi:10.3762/bjoc.16.81

• , and cNMI3H (Table 2 and Table 3, Supporting Information File 1, Tables S2–S4). The redox properties of the new bipyrrole boomerangs were investigated by means of cyclic (CV) and differential pulse (DPV) voltammetry (Supporting Information File 1, Figures S11–S16). All systems showed at least two

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

• . Furthermore, the ability of the new [10]ferrocenophane 2a to bind transition metal cations is outlined, and the redox properties of the new ferrocenophanes are studied by cyclovoltammetry. Results and Discussion The substrates 1a and 1b for the RCAM toward the desired ferrocenophanes 2a and 2b were

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• and imidazolium which can recognize different anions, have been reported in the literature. As a matter of fact, porphyrin macrocycles are used for sensing of anionic compounds by a measurable physical response due to their intrinsic optical and redox properties [38]. Beer and co-workers have

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

• Arnault Heynderickx,
• Sébastien Nénon,
• Olivier Siri,
• Vladimir Lokshin and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

• moieties allows further modifications at these units to achieve fine-tuning of the light absorption and redox properties. In the course of this study, we also expected that these derivatives could serve as interesting components of supramolecular structures that can assemble in a predictable way owing to

Naphthalene diimides with improved solubility for visible light photoredox catalysis

• Barbara Reiß and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 2043–2051, doi:10.3762/bjoc.15.201

• easily incorporated into the core structure in order to tune optical and redox properties. Naphthalene diimides (NDIs) as the smallest possible rylene dyes are such an important class of organic dyes. In contrast to their bigger homologs perylene diimides which were rarely used for photoredox catalysis

• order to tune their optical and redox properties as mentioned above [39][40][52]. The common synthetic approach for core-substituted NDIs (cNDIs) makes tailor-made dyes rather easily accessible. With respect to these unique properties, NDIs should also be explored for photoredox catalysis. We present

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

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• its reversible redox properties and high electron-donating strength (see Figure 1) [26]. In order to promote the delocalization from the electron-donating unit to the electron-withdrawing and anchoring group located on its 8 position, a 2,3,5,6-tetramethyl-BODIPY derivative has been designed (see

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• 3/DSS 4 (28,400 to 20,830 L mol−1 cm−1). No fluorescence was observed for each of the four heteroacenes DTT 1 to DSS 4 neither in DCM nor in THF. Electrochemical properties and electropolymerization The redox properties of the heterotriacenes 1–4 were investigated by means of cyclic voltammetry in

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

• ][16] the interest of using this class of catalysts only gained limited interest during the last years. The advantage of using N-phenylphenothiazine catalysts in photoredox chemistry is attributed to their beneficial redox properties. Moreover, a modification of the core is rather simple and allows

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• absorption and redox properties through well selected ligands [52]. This Ir-based complex reacts in the photoredox catalytical cycle with iodonium salt and (TMS)3SiH as the Ru-based complex in reactions 1, 2 and 3. Moreover, Iridium complexes can be interesting for applications in ring-opening

• polymeric chain), extracted from [103]. Redox properties of additives [1][30][31]. Characteristics of Ru(bpy)32+ [45][46][47][48]. Characteristics of Ir(ppy)3 [40][50][51]: Characteristics of G1 [63][64][65]. Characteristics of FeC1 from [66][67][68]. Characteristics of TADF CuC 4 from [58]. Characteristics

Bioinspired cobalt cubanes with tunable redox potentials for photocatalytic water oxidation and CO₂ reduction

• Zhishan Luo,
• Yidong Hou,
• Jinshui Zhang,
• Sibo Wang and
• Xinchen Wang

Beilstein J. Org. Chem. 2018, 14, 2331–2339, doi:10.3762/bjoc.14.208

• redox potentials reflect a dependence on the electronic properties of the ligand. This again underlines, that the ligands are playing a significant role in the regulation of the redox properties of the 1-R complexes. To further estimate the impact of ligand substitution, the complexes were analyzed by

Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

• Cristina Morar,
• Pedro Lameiras,
• Attila Bende,
• Gabriel Katona,
• Emese Gál and
• Mircea Darabantu

Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

• branch-cells, (ii) basicity and conformational nature of the diaza-six-membered saturated heterocycle as linker and (iii) the global molecular shape, the resulted 4-aminophenol-based melamines displayed relevant redox properties [36] and, in some cases, selective aptitudes to produce MOFs (metal-organic

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• ; electroluminescence; OLED; phosphorescence; platinum complexes; Introduction Photoactive TMCs have attracted enormous attention in the last two decades because of their peculiar photophysical and rich redox properties, which make them appealing from both fundamental research and technological applications points of

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• remarkable optical and redox properties, azulene proved to be an excellent building block for developing a large variety of materials ranging from NLO chromophores [13] to molecular switches [14][15] and liquid crystals [16] or high-conductance materials [17]. In contrast to most aromatic compounds which

• , azulene→terpy, though different functionals are not consistent in depicting the contributing ratios of these various components of electronic transitions. Electrochemical properties The redox properties of 4a and 4b were investigated using cyclic voltammetry (CV) and differential pulse voltammetry (DPV

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• -bonding modes arise in the supramolecular polymeric network, i.e., an intramolecular H bonding with the β- and γ-phosphate groups of ATP2− and an intermolecular H bond between the α-phosphate and another amidoferrocenyl group. Redox properties of polycationic copolymers containing the complex [Fe(η5-C5H5

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• self-aggregated in chloroform–dioxane to form a gel. TEM images of the xerogel exhibited helical molecular tapes nanometer wide and micrometer long. A cyclic voltammetry (CV) study on 2b showed the redox properties expected for Pc and TTF, and doping of 2b in CH2Cl2 with I2 produced a radical cation

Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes

• Luke J. O’Driscoll,
• Sissel S. Andersen,
• Marta V. Solano,
• Dan Bendixen,
• Morten Jensen,
• Troels Duedal,
• Jess Lycoops,
• Cornelia van der Pol,
• Rebecca E. Sørensen,
• Karina R. Larsen,
• Kenneth Myntman,
• Christian Henriksen,
• Stinne W. Hansen and
• Jan O. Jeppesen

Beilstein J. Org. Chem. 2015, 11, 1112–1122, doi:10.3762/bjoc.11.125

• Southern Denmark, Campusvej 55, DK-5230, Odense M, Denmark 10.3762/bjoc.11.125 Abstract The electron-donor and unique redox properties of the tetrathiafulvalene (TTF, 1) moiety have led to diverse applications in many areas of chemistry. Monopyrrolotetrathiafulvalenes (MPTTFs, 4) and

Single-molecule conductance of a chemically modified, π-extended tetrathiafulvalene and its charge-transfer complex with F₄TCNQ

• Raúl García,
• M. Ángeles Herranz,
• Edmund Leary,
• M. Teresa González,
• Gabino Rubio Bollinger,
• Marius Bürkle,
• Linda A. Zotti,
• Yoshihiro Asai,
• Fabian Pauly,
• Juan Carlos Cuevas,
• Nicolás Agraït and
• Nazario Martín

Beilstein J. Org. Chem. 2015, 11, 1068–1078, doi:10.3762/bjoc.11.120

• carbonyl groups appear at 192.4 ppm and the carbons of the alkyne moieties at 88.0 and 90.4 ppm, with the terminal methyl groups at 28.7 ppm. The redox properties of compound 5 (0.2 mM) were determined by cyclic voltammetry at room temperature in THF using TBAPF6 (0.1 M) as a supporting electrolyte under

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

• ; Introduction Thanks to its remarkable redox properties and strong π-donating character demonstrated with the pioneering work of F. Wudl in the early 1970s [1], tetrathiafulvalene (TTF) has become one of the most popular electroactive frameworks used in materials science [2][3][4][5]. In addition to the well

• checked the influence of the redox properties towards binding ability by studying the strong electrodeficient acceptor F4-TCNQ. Interaction with 1,3-dinitrobenzene (m-DNB) The host–guest affinity was detected by UV–visible spectroscopy upon titration of clip 3 (10−3 M in o-C6H4Cl2) with addition of m-DNB

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

• electronic and electrochemical redox properties were characterized by UV–vis spectroscopic and cyclic voltammetric analyses. The carboxyl-TTFV was applied as a redox-active ligand to complex with Zn(II) ions, forming a stable Zn-TTFV coordination polymer. The structural, electrochemical, and thermal

• in these molecules are still retained at a similar level in the ground state. The electrochemical redox properties of compounds 4–9 were characterized by cyclic voltammetry, and the detailed cyclic voltammograms are shown in Figure 2. For methyl ester-appended DTF 4 (Figure 2A) an anodic peak was

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

• . The redox properties of this donor were studied by cyclic voltammetry in dichloromethane using [n-Bu4N][PF6] as the supporting electrolyte (Figure 4) showing two one-electron quasi-reversible redox waves at 0.405 V and 0.850 V vs Ag/AgNO3 as typical of TTF donors, which are ascribed to the couples

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

• absorption of all the compounds at λmax 779 nm (ε 210 M−1cm−1), but of significantly lower intensity than the charge-transfer absorptions of the TEE compounds. Electrochemistry The redox properties of the TTF-bridge-TTF molecules were investigated by cyclic voltammetry and differential pulse voltammetry in

• TTF dimer tetracations. As already extensively discussed in [32] concerning the redox properties of self-assembled polyelectrolyte multilayers, consisting of well-defined water-soluble electronically conducting poly-3-(30-thienyloxy)propyltriethylammonium, the spinless doubly charged species can be

Trifluoromethyl-substituted tetrathiafulvalenes

• Olivier Jeannin,
• Frédéric Barrière and
• Marc Fourmigué

Beilstein J. Org. Chem. 2015, 11, 647–658, doi:10.3762/bjoc.11.73

• will be described, based on the X-ray crystal structure analyses of four neutral TTF derivatives, i.e., the EDT-TTF derivatives 2ac and 2bc and the tetrasubstituted derivatives 3bc and 4bc. Redox properties Cyclic voltammetry was used to evaluate the evolution of the donor strength with the nature and