Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• It is known that phenylhydrazone groups are able to act as optical sensors particularly for fluoride anions [41][42][43][44][45]. Thus, the colorimetric sensing abilities of the two ligands L1 and L2 were investigated by adding various anions such as hydrogensulfate, acetate, iodine and fluoride

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• demonstrate the extensive use of RCM in the synthesis of different metallophanes involving ferrocenophane (e.g., 206) [160] and other metallophanes [161][162][163][164]. The synthesis of mechanically interlocked molecules such as catenanes and rotaxanes which are used to assemble molecular machines, sensors

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

• amidation of aryl halides [51][52]. Examples of TTF derivatives synthesised using this protocol by other groups include: MPTTF and BPTTF-triarylamine conjugates (as possible charge-transport materials) [53], MPTTF-triarylborane conjugates (with possible applications as fluoride sensors) [54], and MPTTF

• materials with applications in supramolecular chemistry, molecular electronics and as sensors. The sequential, reversible oxidation of TTF (1) to its stable radical cation (2) and dication (3) states. Structures and possible substitution positions of MPTTFs (4) and BPTTFs (5). Large-scale synthesis of 6

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

• the use of single molecules as chemical sensors, in which analyte molecules may bind to a backbone to alter its conductance. Further combinations of donors and acceptors should be explored in order to evaluate this potential. Depictions of 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (exTTF

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

• giving rise to three stable redox states) characteristics, more and more sophisticated TTF-based supramolecular systems have been designed, being able to operate as machines, chemical sensors, redox-switchable ligands, molecular shuttles, molecular switches and logic gates [11]. Considering that

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• is a piezoelectronic semiconductor with a high exciton binding energy (60 meV) and a wide band-gap (3.37 eV) at room temperature [17][18]. ZnO is therefore employed in (bio-)sensors [19], ultraviolet (UV) light-emitting diodes [20], UV laser diodes [21] and in the field of catalysis [22][23]. ZnO

Fluoride-driven ‘turn on’ ESPT in the binding with a novel benzimidazole-based sensor

• Kai Liu,
• Xiaojun Zhao,
• Qingxiang Liu,
• Jianzhong Huo,
• Bolin Zhu and
• Shihua Diao

Beilstein J. Org. Chem. 2015, 11, 563–567, doi:10.3762/bjoc.11.61

• recognition and sensing, was suggested to be responsible for the fluorescence enhancement with a blue shift of 35 nm in the emission spectrum. Keywords: anion recognition; deprotonation; ESPT; fluoride; ‘turn on’ fluorescence; Introduction Design and synthesis of selective and efficient sensors for various

• anions involved in biological, industrial and environmental processes have drawn a lot of attention [1][2][3]. In recent years, much effort has been devoted to the development of anion fluorescent sensors [4]. Of particular interest concerning anion recognition and sensing was fluoride [5][6][7], as it

• is important to human health (for example, dental care, osteoporosis and osteosarcoma). To realize the high selectivity and sensitivity to fluoride, many anion fluorescent sensors have been designed based upon numerous signal mechanisms [4][8][9][10]. However, excited-state intra/intermolecular

Electrochemical oxidation of cholesterol

• Jacek W. Morzycki and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45

• ]. An interesting technique for non-enzymatic sensors represents molecularly imprinted self-assembled monolayers. In this approach, the layer containing organic compounds together with cholesterol is deposited on an electrode surface. Then, the cholesterol is removed from the layer, and the oxidation

• ]. These sensors have been proved to be useful for analyzing food samples [74]. Non-enzymatic direct electrochemical oxidation of cholesterol The third class represents sensors based on the direct electrochemical oxidation of cholesterol. The authors claim that the process occurs on nanoporous electrodes

Synthesis and chemosensing properties of cinnoline-containing poly(arylene ethynylene)s

• Natalia A. Danilkina,
• Petr S. Vlasov,
• Semen M. Vodianik,
• Andrey A. Kruchinin,
• Yuri G. Vlasov and
• Irina A. Balova

Beilstein J. Org. Chem. 2015, 11, 373–384, doi:10.3762/bjoc.11.43

• Optical sensors provide an efficient and sensitive approach for the rapid detection and identification of a wide range of chemical substrates by measuring the changes of optical properties such as absorbance, reflectance, luminescence, or fluorescence [1]. Among them a type of sensors based on conjugated

• exciton are spatially separated, the quenching amplification factor is only limited by the diffusion distance of the exciton. In practice, a single bound analyte molecule can deactivate excitons within 130 neighboring phenylene ethynylene repeating units [4]. Sensors based on CPs can be classified either

• . Such materials find widespread use in sensing of metal ions and anions, detection of explosives and various biomolecules [2−4]. Among the great variety of known conjugated polymers, poly(arylene ethynylene)s (PAEs) are one of the most promising materials in the search for new chemical sensors [7]. A

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

• ][17][18]. This approach offers self-assembled monolayers (SAMs) which can be utilized for derivatization of gold electrodes for the construction of electrochemical sensors [19][20] or even for the development of molecular printboards [21]. These results imply that the structure of CD derivatives

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

• Anastasia S. Kostyuchenko,
• Vyacheslav L.Yurpalov,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

• as organic semiconductors in light emitting diodes (OLED’s), field effect transistors (FETs), electrochemical and chemical sensors and other organic electronic devices [1][2][3][4][5]. This family of organic semiconductors is especially interesting because they can be rendered solution processable

Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C₆₀

• Marco Caricato,
• Silvia Díez González,
• Idoia Arandia Ariño and
• Dario Pasini

Beilstein J. Org. Chem. 2014, 10, 1308–1316, doi:10.3762/bjoc.10.132

• cyclic adducts exhibit recognition properties towards C60 in toluene solutions (up to log Ka = 3.2) with variable stoichiometries and variable intensities of the charge-tranfer band upon complexation. Keywords: BINOL; C60; carbon nanomaterials; carbon nanostructures; chirality; macrocycles; sensors

• . These binaphthyl-based hosts may also be utilized as chiroptical sensors for chiral carbon-based nanomaterials in functional nanochemical environments. Experimental General experimental. All commercially available compounds were purchased from commercial sources and used as received. Compounds (R)-1 [40

Nonanebis(peroxoic acid): a stable peracid for oxidative bromination of aminoanthracene-9,10-dione

• Vilas Venunath Patil and
• Ganapati Subray Shankarling

Beilstein J. Org. Chem. 2014, 10, 921–928, doi:10.3762/bjoc.10.90

• benzanthrone are widely used as intermediates for pharmaceuticals [1][2][3], for medicinal applications [4], as dyes [5][6][7][8][9] and in Hg2+ ion sensors [10]. Although these bromo derivatives have a wide range of applications, it is difficult to carry out their bromination as the two carbonyl groups of

Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability

• Malamatenia D. Manouilidou,
• Yannis G. Lazarou,
• Irene M. Mavridis and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 774–783, doi:10.3762/bjoc.10.73

• specific guest molecules. The oligomers are reported to display improved to significantly enhanced binding capacity as well as superior molecular recognition ability [12][13][14], compared to the natural CDs. Suitable design has resulted in better hosts for applications as sensors and catalysts [15], hosts

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• [5] or of optical sensors [6]. Certain stimuli-responsive materials are characterized by the presence of thioethers in the main chain. Tirelli et al. investigated the oxidation-responsive behavior of thioethers for biomedical applications [7][8][9][10]. The stimulus of these mostly poly(propylene

Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide

• Richard J. Ingham,
• Claudio Battilocchio,
• Joel M. Hawkins and
• Steven V. Ley

Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56

• ., sensors, pumps, heaters, etc.), these unified interfaces would provide the desired flexibility between devices. In this way, more time can be spent on the engineering and chemistry challenges inherent in the synthesis process, rather than the logistics of control system interfaces. Our group has

• analytical technologies (PAT), a number of parameters are read from devices or sensors, and the effluent is only collected when all of the parameters are stable, ensuring a high degree of purity in the collected material. Larger zirconia columns were also used to improve the throughput. Employing 5 g of

• devices is combined into a single interface. The sensors were interrogated approximately once a second; a Raspberry Pi® microcomputer (as shown in Figure 5b) has more than sufficient processing power to perform the required data collection, interpretation and control. We anticipate that much more complex

Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers

• Dae Won Cho,
• Patrick S. Mariano and
• Ung Chan Yoon

Beilstein J. Org. Chem. 2014, 10, 514–527, doi:10.3762/bjoc.10.47

• to which various kinds of donor functionality can be appended. By employing this approach, a number of lariat-type azacrown ethers including 72–74 which possess aminoether and thioether side chains, have been prepared. Lariat-type crown ether-based fluorescence sensors for heavy metal ions Since the

• SET-promoted photocyclization reactions of donor–acceptor-linked substrates could be employed in practical and efficient routes for the preparation of new metal cation-fluorescence sensors. As described earlier by de Silva and others [74][75][76][77][78][79], SET based fluorescence sensors are useful

Continuous flow nitration in miniaturized devices

• Amol A. Kulkarni

Beilstein J. Org. Chem. 2014, 10, 405–424, doi:10.3762/bjoc.10.38

• ). The selectivity of the desired product 37 was improved under flow conditions. A continuous flow silicon-glass microreactor equipped with multiple functionalities such as multistream micromixer, reaction channel, large-area cooling chamber, and five integrated miniature temperature sensors was used

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

• Christina Lohoelter,
• Malte Brutschy,
• Daniel Lubczyk and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2013, 9, 2821–2833, doi:10.3762/bjoc.9.317

• significant application as receptors and chemical sensors in the detection of aromatic compounds [16][17][18][19][20]. Thus, the first artificial receptor for caffeine had been established [21][22]. The introduction of chiral information onto a supramolecular entity gave rise for enantiofacial differentiation

Temperature measurements with two different IR sensors in a continuous-flow microwave heated system

• Jonas Rydfjord,
• Fredrik Svensson,
• Magnus Fagrell,
• Jonas Sävmarker,
• Måns Thulin and
• Mats Larhed

Beilstein J. Org. Chem. 2013, 9, 2079–2087, doi:10.3762/bjoc.9.244

• will influence most traditional methods of temperature measurement. Thus, we used a microwave transparent fiber optic probe, capable of measuring the temperature inside the reactor, and investigated two different IR sensors as non-contact alternatives to the internal probe. IR sensor 1 measures the

• temperature on the outside of the reactor whilst IR sensor 2 is designed to measure the temperature of the fluid through the borosilicate glass that constitutes the reactor wall. We have also, in addition to the characterization of the before mentioned IR sensors, developed statistical models to correlate the

• of IR sensors and find the best way to correlate the “real” internal temperature of the reactor to the reading from the IR sensor in order to be able to apply a calibration to the IR sensor reading. We opted for linear multiple regression models using the full dataset, with all the measured data

Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

• Laura Bekere,
• David Gachet,
• Vladimir Lokshin,
• Wladimir Marine and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2013, 9, 1311–1318, doi:10.3762/bjoc.9.147

• to be efficient fluorescent molecular probes [7][8]. Recently, the potential of amino-1,8-naphthalimides as fluorescent sensors in living cells has been reviewed [9]. Dendrimers involving the amino-1,8-naphthalimide moieties were showed to be promising active nondoping emitters [10]. 4-Amino

Camera-enabled techniques for organic synthesis

• Steven V. Ley,
• Richard J. Ingham,
• Matthew O’Brien and
• Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

• for a “Lab of the Future” [16][17][18] we anticipate further integration of a multitude of wirelessly connected devices such as environmental sensors, tablet computers for displaying and recording data, and novel information aids such as safety goggles incorporating head-up displays, which might be

• provides a shielded reaction chamber for conducting preparative chemistries at high temperatures and high pressures usually in batch mode in sealed vessels or in some cases in flow [40][48]. While it is easy to record reaction times, temperatures and pressures by using the inbuilt sensors, this is a

Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

• Paul M. Hershberger,
• Satyamaheshwar Peddibhotla,
• E. Hampton Sessions,
• Daniela B. Divlianska,
• Ricardo G. Correa,
• Anthony B. Pinkerton,
• John C. Reed and
• Gregory P. Roth

Beilstein J. Org. Chem. 2013, 9, 900–907, doi:10.3762/bjoc.9.103

• oligomerization domain-1 (NOD1) inhibition (ML130 and ML146): The second program targeted proteins in the mammalian innate immune system that confer defense by detection of specific microbial ligands, or pathogen-associated molecular pattern microbial sensors known to house NOD1 (nucleotide-binding

Superstructures of fluorescent cyclodextrin via click-reaction

• Arkadius Maciollek,
• Helmut Ritter and
• Rainer Beckert

Beilstein J. Org. Chem. 2013, 9, 827–831, doi:10.3762/bjoc.9.94

• used as potentially biological markers, as molecular sensors, or for chiral recognition in aqueous solution [11][12][13]. Thus, in this present paper we describe the spectroscopic and structural behavior of a “CD-Click-Fluorophore” in the absence and presence of a competitive guest in water. Results

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

• pressure sensors as well as optical devices. The article begins with a brief description of the principle of molecular spin state switching using simple concepts of ligand field theory. Conditions to be fulfilled in order to observe spin crossover will be explained and general remarks regarding the

• spectacular is the change of magnetic behavior and color, which has made such SCO substances very attractive because of their potential for practical applications, e.g., as switching devices and sensors. A thermally induced change of spin state (spin transition, spin crossover) was first reported some eighty