Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

• Thanh-Tuân Bui,
• Fabrice Goubard,
• Malika Ibrahim-Ouali,
• Didier Gigmes and
• Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

• with the azasiline donor, OLEDs displaying the unprecedented EQE of 22.3% were obtained [46]. As specificity, azasiline is a 6-membered heterocycle comprising a silicon atom introduced instead of a carbon atom to enlarge the HOMO–LUMO gap and lower the HOMO level. Due to the sp3 hybridization of the

• silicon atom, two phenyl rings can be introduced on the silicon-bridged structure providing bulkiness and rigidity to the donor. Intermolecular interactions are thus efficiently prevented and the conformation disorder drastically reduced. When used as electron donor in T1, a ΔEST of 0.14 eV was determined

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• following standard surface-hybridization protocols. The use of the solid support assay format also allows detection of DNA directly from the fluorescence signal of the CPP bound to the solid support without requiring labeling on the PNA probe [126]. Polystyrene microbeads self-assembled on patterned silicon

Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity

• Tathagata Mukherjee,
• Soumik Biswas,
• Andreas Ehnbom,
• Subrata K. Ghosh,
• Ibrahim El-Zoghbi,
• Nattamai Bhuvanesh,
• Hassan S. Bazzi and
• John A. Gladysz

Beilstein J. Org. Chem. 2017, 13, 2486–2501, doi:10.3762/bjoc.13.246

• species have never been described in the literature. Silicon has been used as a locus for branching, as exemplified by a variety of highly fluorophilic compounds of the formula (RfnCH2CH2)3SiZ (see XI in Scheme 7, Z = 4-C6H5X [53][54]). However, these feature silicon–carbon and sp3 carbon–hydrogen bonds

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• -b]phosphole dioxides (Figure 1A) [25][26] and benzophosphole-fused tetracyclic heteroacenes, containing boron (B) [27][28][29], silicon (Si) [30], oxygen (O) [31], and sulfur (S) [32][33][34] (Figure 1B), were synthesized and their physical properties were studied. However, to the best of our

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• step. As suggested in the initial works of McKenna, the mechanism occurs by an oxophilic substitution on the silicon atom whereas bromide acts as a leaving group to produce the intermediate I (Figure 14). This intermediate is then dealkylated following a similar path than that occurring with the

• the terminal oxygen doubly bonded to the phosphorus atom was indeed the nucleophilic atom that attacks the silicon atom [159]. Regarding the mechanism of this reaction, the oxophilic silylation involving the oxygen atom which is doubly bonded to the phosphorus atom, thus producing the intermediate I

Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• Thematic Series in the article by Leclercq [19]. For example, β-CD was immobilized onto a silicon substrate and incubated with various bacteria. These bacteria could be captured nearly quantitatively at the surface and released again by competitive binding with free methylated β-CD [20]. The proteins

Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane

• James R. Vyvyan,
• Courtney A. Engles,
• Scott L. Bray,
• Erik D. Wold,
• Christopher L. Porter and
• Mikhail O. Konev

Beilstein J. Org. Chem. 2017, 13, 2122–2127, doi:10.3762/bjoc.13.209

• ; palladium; silicon; Introduction The development of transition metal-catalyzed cross-coupling technologies over the last four decades revolutionized the synthetic chemistry. Indeed, the importance of Pd-catalyzed coupling was recognized with the 2010 Nobel Prize awarded to Heck, Negishi and Suzuki [1][2

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• attachments that could provide more flexibility in the synthesis of longer oligosaccharides [62][65]. Some representative examples of this general concept include benzyl–silicon tether [72], which is a hybrid approach to xylylene and a regular silicon [59] type of tethering. Another example of a non

• significantly higher yields in comparison to those reported in the original protocols. Since the IAD has been overviewed multiple times [41][48][49][50], presented herein are only the basics as well as the key recent developments of this. Stork and Bols independently demonstrated that silicon bridge-mediated

• studies by Stork and Bols, Montgomery et al. further expanded the idea of the long range IAD via silicon tethering [90]. In the most recent report, they hypothesized that the conformational restriction of the pyranose should position the C-6 oxygen of the donor away from the developing oxacarbenium

High-speed vibration-milling-promoted synthesis of symmetrical frameworks containing two or three pyrrole units

• Marco Leonardi,
• Mercedes Villacampa and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2017, 13, 1957–1962, doi:10.3762/bjoc.13.190

• functionalized spacers is interesting in that they may allow additional interactions with biological targets. Furthermore, the tetramethyldisiloxane derivatives are of relevance in view of the current interest in silicon-containing compounds for drug discovery applications, which has led to the “silicon switch

2-Methyl-2,4-pentanediol (MPD) boosts as detergent-substitute the performance of ß-barrel hybrid catalyst for phenylacetylene polymerization

• Julia Kinzel,
• Daniel F. Sauer,
• Marco Bocola,
• Marcus Arlt,
• Tayebeh Mirzaei Garakani,
• Andreas Thiel,
• Klaus Beckerle,
• Tino Polen,
• Jun Okuda and
• Ulrich Schwaneberg

Beilstein J. Org. Chem. 2017, 13, 1498–1506, doi:10.3762/bjoc.13.148

• improved. Recent examples are the construction of metatheases [3][4], asymmetric transfer hydrogenases [5][6], Diels-Alderases [7][8][9][10], an enzyme for carbon–silicon bond formation [11], a phenylacetylene polymerase [12][13] and others [14][15][16][17]. A challenge to overcome are unintended substrate

Interactions between shape-persistent macromolecules as probed by AFM

• Johanna Blass,
• Jessica Brunke,
• Franziska Emmerich,
• Cédric Przybylski,
• Vasil M. Garamus,
• Artem Feoktystov,
• Roland Bennewitz,
• Gerhard Wenz and
• Marcel Albrecht

Beilstein J. Org. Chem. 2017, 13, 938–951, doi:10.3762/bjoc.13.95

• measurements. Small-angle neutron and X-ray (SANS/SAXS) scattering experiments confirm the stiffness of the polymer chains with an apparent contour length of about 130 Å. Surface modification of planar silicon wafers as well as AFM tips was realized by covalent bound formation between the terminal amino groups

• AFM tip and found enhancement factors up to 2, depending on the force loading rate [46]. We have previously explored the adhesion characteristics of dense CD layers on an AFM tip and a planar silicon surface connected by various ditopic linker molecules. In this system we were able to switch adhesion

• concentration of connector 9 necessary for the almost complete precipitation of the host polymer 8 can be explained by the high integrability of the host–guest system based on the shape-persistence of the polyconjugated polymer backbone of 8. Attachment of polymer 8 to silicon surfaces Planar silicon wafers, as

Fast and efficient synthesis of microporous polymer nanomembranes via light-induced click reaction

• Qi An,
• Youssef Hassan,
• Xiaotong Yan,
• Peter Krolla-Sidenstein,
• Tawheed Mohammed,
• Mathias Lang,
• Stefan Bräse and
• Manuel Tsotsalas

Beilstein J. Org. Chem. 2017, 13, 558–563, doi:10.3762/bjoc.13.54

• using light-induced TYC reaction in the presence of the photoinitiator 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one. IRRA-Spectrum of the CMP thin film on a gold-coated silicon wafer and the corresponding band assignments. AFM image and line-scan across the edge of the CMP thin film. SEM

Diels–Alder reactions of myrcene using intensified continuous-flow reactors

• Christian H. Hornung,
• Miguel Á. Álvarez-Diéguez,
• Thomas M. Kohl and
• John Tsanaktsidis

Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15

• circumstances of this side-reaction are unknown; it only occurred in the stainless steel reactor and not in the PFA tubing of the Vapourtec R-series flow reactor or the silicon carbide module of the plate flow reactor. Hence, it was postulated that a metal catalyzed polymerisation on the stainless steel reactor

• silicon carbide plate-type flow reactor. Two reactant solutions were prepared, one containing myrcene (208.2 g of myrcene stock solution with a 90% purity, 1.375 mol of myrcene) in toluene (21.2 mL), and the other containing 2b (90.1 g, 1.250 mol), in toluene (80.1 mL). The two feed solutions were pumped

• a series of 3M™ silicon carbide microstructured plates (see also Figures S2 and S3 in Supporting Information File 1), which was thermally regulated by a Lauda Integral XT 150 heater/chiller unit. The total reactor volume was 105 mL. An SSI Prep 100 dual piston pump with PEEK pump heads was used to

Silyl-protective groups influencing the reactivity and selectivity in glycosylations

• Mikael Bols and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2017, 13, 93–105, doi:10.3762/bjoc.13.12

• or high stereoselectivity. This mini review will summarize these findings. Keywords: Carbohydrate; conformation; glycosylation; reactivity; selectivity; Introduction Silicon-based protective groups of alcohols have a long history in organic chemistry [1][2][3]. The most popular and commercially

• provide an alternative orthogonal protective group to the more conventional acetyl, benzoyl and benzyl groups. Particularly in oligosaccharide synthesis where many orthogonal hydroxy protective groups are required silicon protective groups have frequently been introduced in both glycosyl donors and

• benzoylated thioglycosides with high chemoselectivity and was therefore used in a range of high yielding oligosaccharide syntheses [38]. The bifunctional silicon protective group DTBS (Figure 1) has been used both to increase and decrease the reactivity of glycosyl donors. The 4,6-O-DTBS-protected

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

• Serena Traboni,
• Emiliano Bedini and
• Alfonso Iadonisi

Beilstein J. Org. Chem. 2016, 12, 2748–2756, doi:10.3762/bjoc.12.271

• protecting groups are featuring the presence of hindered substituents at silicon such as in tert-butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) groups. Their bulkiness allows in many cases regioselective silyl protection of primary alcohols. Commonly, O-silylation is performed by exposing the

The direct oxidative diene cyclization and related reactions in natural product synthesis

• Juliane Adrian,
• Leona J. Gross and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

• ) and then successfully connected in a silicon-tethered ring closing metathesis (RCM) [98] to provide the main backbone of cis-sylvaticin (40). Moreover, in 2009, Brown and co-workers reported on a short synthesis of the non-adjacent bis-THF core of cis-sylvaticin (40) making use of a permanganate

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• recorded by a Keithley 236 source-measure unit under AM1.5G simulated solar irradiation, 100 mW/cm2 (Abet Technologies Sun 2000 Solar Simulator). The light intensity was determined by a calibrated silicon solar cell fitted with a KG5 color glass filter to bring spectral mismatch to unity. The active area

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• AM 1.5G solar illumination at 100 mW cm−2 (1 sun), using a Xe lamp-based Bunko-Keiki SRO-25 GD solar simulator. The light intensity was calibrated using a standard silicon photovoltaic reference cell. Chemical structures of TTA-DPP4 and TTA-DPP2. HOMO and LUMO distributions, calculated energy levels

Biradical vs singlet oxygen photogeneration in suprofen–cholesterol systems

• Fabrizio Palumbo,
• Francisco Bosca,
• Isabel M. Morera,
• Inmaculada Andreu and
• Miguel A. Miranda

Beilstein J. Org. Chem. 2016, 12, 1196–1202, doi:10.3762/bjoc.12.115

• photolysis cell in right-angle geometry. An excimer laser (LEXTRA50 Lambda Physik) was used for the excitation at 308 nm (laser excitation at 5 low-pulse energies for each molecule). A 5 mm thick (5 cm in diameter) 1050 nm cut-off silicon filter and a 1270 nm interference filter were placed between the diode

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• conventional silicon-based semiconductors. Organic semiconducting materials can be used as active layers in organic field-effect transistors (OFETs) [1][2][3][4][5][6][7], organic light-emitting diodes (OLEDs) [8][9][10], and organic photovoltaics (OPVs) [11][12]. Among many organic semiconducting materials so

Art, auto-mechanics, and supramolecular chemistry. A merging of hobbies and career

• Eric V. Anslyn

Beilstein J. Org. Chem. 2016, 12, 362–376, doi:10.3762/bjoc.12.40

• beads placed in micromachined divots on a silicon chip (Figure 9A), and solvents and samples were introduced to the system via an external HPLC [69]. While the miniature nature of the system was intriguing, such a device was going to be difficult for supramolecular chemists to adopt. More user-friendly

Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates

• Michael Edmunds,
• Mohammed Abdul Raheem,
• Rebecca Boutin,
• Katrina Tait and
• William Tam

Beilstein J. Org. Chem. 2016, 12, 239–244, doi:10.3762/bjoc.12.25

• bridgehead carbon appears to impact the reactions’ outcome by hindering access to the site of carbo-palladation. SiMe3 gave a moderate yield of 64% (Table 3, entry 4). The silicon–carbon bond is longer than carbon–carbon bonds, making TMS less bulky than its hydrocarbon counterparts. Both of the electron

Bright molecules for sensing, computing and imaging: a tale of two once-troubled cities

• A. Prasanna de Silva

Beilstein J. Org. Chem. 2015, 11, 2774–2784, doi:10.3762/bjoc.11.298

• modern manifestations of these processors are the logic gates cut from silicon. Of course, stored-program computers (as the name suggests) require software in order to command and coordinate complex computations. I was fortunate to receive programming instruction from Gihan Wickramanayake (University of

• interface somewhat akin to those found in a touch-screen of a mobile telephone or in a mouse-driven screen of a stored-program computer. The treated paper could build an image after receiving a projection of the object. We do this by using a photoacid generator 6 (used to sculpt features in silicon chips

Pyridylidene ligand facilitates gold-catalyzed oxidative C–H arylation of heterocycles

• Kazuhiro Hata,
• Hideto Ito,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2015, 11, 2737–2746, doi:10.3762/bjoc.11.295

• mmol), 2-iodosobenzoic acid (IBA, 53 mg, 0.20 mmol), 10-camphorsulfonic acid (CSA) (47 mg, 0.20 mmol) and a stir bar were placed in a screw test tube, and dry CHCl3/MeOH (1.0 mL/0.10 mL) was added under N2 atmosphere. The tube was sealed with a cap equipped with a Teflon®-coated silicon rubber septum

• added under N2 atmosphere. The tube was sealed with a cap equipped with a Teflon®-coated silicon rubber septum and heated at 65 °C for 30 min. After cooling to room temperature, LiCl (8.4 mg, 0.20 mmol) was added. 1,1,2,2-Tetrachloroethane was added as an internal standard and an NMR yield of AuCl3(PyC