Binding abilities of a chiral calix[4]resorcinarene: a polarimetric investigation on a complex case of study

• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2698–2709, doi:10.3762/bjoc.13.268

• : calix[4]resorcinarene; host–guest complexes; p-nitroanilines; polarimetry; supramolecular chemistry; Introduction During the last decades calix[n]arenes and calix[n]resorcinarenes (CAs) have emerged as versatile supramolecular host systems for various applications [1][2][3][4][5], spanning from sensors

Development of a fluorogenic small substrate for dipeptidyl peptidase-4

• Futa Ogawa,
• Masanori Takeda,
• Kanae Miyanaga,
• Keita Tani,
• Ryuji Yamazawa,
• Kiyoshi Ito,
• Atsushi Tarui,
• Kazuyuki Sato and
• Masaaki Omote

Beilstein J. Org. Chem. 2017, 13, 2690–2697, doi:10.3762/bjoc.13.267

• probes can act as good sensors for enzymes but the fluorophore unit is usually large because fused aromatic rings and an elongated π-conjugated system are necessary to impart appropriate fluorescent properties to the probe [14]. The molecular size of the fluorescent probe is therefore large, which is

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• mechanism of sensing involves Hg(II) ion coordination to two thymine moieties followed by pyrene excimer formation [19]. Furthermore, compound A2 and adenine derivative A3 were reported to act as fluorescent sensors for thymine and adenine [23]. To the best of our knowledge, pyrene–nucleobases have not been

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

• Melanie Denißen,
• Alexander Kraus,
• Guido J. Reiss and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

• class particularly attractive for the development of novel sensors and fluorescent dyes [38], for instance 6-chloro-2,3-naphthaleneimide derivatives were successfully used for labeling amino acids, and for studying peptide protein interactions [39]. Even the superficial attachment to a binding domain

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• sensors [51]. Due to the strong electronegativity of fluorine, the acidity of these pyrrole rings is increased in TFEO-H2Pc. For this reason, it is susceptible to deprotonation, whereas protonation hardly occurs. Trifluoroethoxy-substituted nickel phthalocyanine (TFEO-NiPc) and trifluoroethoxy-substituted

New bio-nanocomposites based on iron oxides and polysaccharides applied to oxidation and alkylation reactions

• Daily Rodríguez-Padrón,
• Alina M. Balu,
• Antonio A. Romero and
• Rafael Luque

Beilstein J. Org. Chem. 2017, 13, 1982–1993, doi:10.3762/bjoc.13.194

• have the additional advantage of easy recycling and reuse, which is an essential and desired property in many applications such as catalysis, sensors and even medicine [2][6][8][9]. Our research group has recently prepared different types of metal and metal oxide nanoparticles which have several

Mechanochemical synthesis of thioureas, ureas and guanidines

• Vjekoslav Štrukil

Beilstein J. Org. Chem. 2017, 13, 1828–1849, doi:10.3762/bjoc.13.178

• application as organocatalysts and sensors. On the other hand, the specific and unique nature of each of these functionalities render (thio)ureas and guanidines as the key constituents of pharmaceuticals and other biologically active compounds. Keywords: guanidines; mechanochemistry; solid state synthesis

• years, molecules with incorporated (thio)urea and guanidine subunits, due to their ability to coordinate other molecules and ions via N–H hydrogen bonding, have also been considered as organocatalysts and anion sensors [7][8][9][10][11][12]. In Scheme 2, several examples of (thio)urea- and guanidine

• paper, the ball milling approach was then applied for a quantitative click-mechanosynthesis of thiourea-based organocatalysts and anion sensors (Scheme 5) [34]. The demonstrated efficiency of mechanochemical milling synthesis of thioureas was exploited for a quantitative transformation of

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

• antigen–antibody interactions during the immune response [40]. Complementarity illustrates a formal correspondence that may be used subsequently as a recognition signal. It manages information as signals in sensor–receptor interactions. This is exploited in living organisms in the way sensors monitor

Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates

• Anna Wrona-Piotrowicz,
• Marzena Witalewska,
• Janusz Zakrzewski and
• Anna Makal

Beilstein J. Org. Chem. 2017, 13, 1032–1038, doi:10.3762/bjoc.13.102

• ; pyrene; thioamide; Introduction Direct functionalization of pyrene 1 has attracted a great deal of attention in recent years because it is the most straightforward route to novel organic molecular materials for optoelectronic devices (OLEDs, field-effect transistors, fluorescent sensors, dye lasers, etc

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• temperature profiles inside the reactor. Whenever it is not possible to insert temperature sensors along the flow reactor/microreactor due to its compact dimensions (although miniaturized sensors are available almost everywhere), the temperature should be monitored at the inlet (preferably at mixing points

• variables are the most critical part of the process control. The process variables that are often measured are temperature, pressure, flow, liquid level, density, composition, pH and viscosity. Details of different sensors or transmitters for measuring these variables can be found in standard process

• be developed to stop the reagents flow first and quench the reaction mass. More importantly, moisture sensors need to be installed on the system to avoid the possible contact of water with n-BuLi. Case study 3: Multistep flow synthesis of rufinamide (telescopic synthesis) Zhang et al. have reported

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

• Nikolay V. Lukashev,
• Gennadii A. Grabovyi,
• Dmitry A. Erzunov,
• Alexey V. Kazantsev,
• Gennadij V. Latyshev,
• Alexei D. Averin and
• Irina P. Beletskaya.

Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55

• serve as sensors for aromatic compounds [24]. During the first decade of the XXI century, the main approaches to cyclic and pincer cholane derivatives were based on “classical” organic transformations (acylation, alkylation, etc.) [7][8][25][26][27]. Later, two modern synthetic approaches based on metal

Spectral and DFT studies of anion bound organic receptors: Time dependent studies and logic gate applications

• Srikala Pangannaya,
• Neethu Padinchare Purayil,
• Shweta Dabhi,
• Venu Mankad,
• Prafulla K. Jha,
• Satyam Shinde and
• Darshak R. Trivedi

Beilstein J. Org. Chem. 2017, 13, 222–238, doi:10.3762/bjoc.13.25

• physiological level. With this in mind, the development of sensors which can detect anions in aqueous media is of special interest. Thus, titration studies of R1 (4.5 × 10−5 M, DMSO/H2O 9:1, v/v) with incremental addition of 0.1 equiv of sodium salts of F− and AcO− ions (10−2 M in distilled H2O) were performed

• sensors towards fluoride ions was demonstrated in commercially available mouthwash. The ability of R1 and R2 to exhibit colorimetric responses to fluoride ions present in commercially available mouthwash demonstrated their practical utility as real time sensors. Based on determined binding constants, the

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• polyhydrazones exhibit a rich coordination chemistry owing to a variety of binding modes and are widely employed as ligands in metal-organic assemblies, sensors and catalytic systems [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. More complex structures containing several hydrazone groups

• 1a was used to ensure complete alkylation). Macrocyclic polynitrogen ligands with several hydrazone arms may be of interest for the design of sensors [52] and contrast agents [53]. Unfortunately, alkylation of ethylenediamine with 4 equivalents of 1a led to an indecipherable mixture of products. In

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

• Laszlo Jicsinszky,
• Marina Caporaso,
• Katia Martina,
• Emanuela Calcio Gaudino and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2016, 12, 2364–2371, doi:10.3762/bjoc.12.230

• well as solvent impurities increase synthesis and purification costs and time. Selectively per-6-thiolated CDs are also used in gold nanoparticle chemistry, particularly in electrochemical sensors [17]. Thiourea (TU) is one of the best precursors of those CDs because as the halogen is exchanged to the

Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element

• Reji Thomas and
• Nobuyuki Tamaoki

Beilstein J. Org. Chem. 2016, 12, 2211–2215, doi:10.3762/bjoc.12.212

• Z-state of azobenzene, (iii) chiral in both states of the azobenzene unit. We have explored the property of planar chirality of these molecules and carried out the optical resolution to demonstrate various properties such as molecular brakes, chiroptical switches and chirality sensors for light and

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• sequence. This turned out to be an ideal problem to address using DCC, and we have now developed a number of synthetic receptors for methylated lysine and arginine that have applications as sensors for these modifications (Figure 6). Lessons learned As a child, my parents said that I “marched to my own

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

• have been investigated for their potential applications in catalysis, photovoltaic cells and biomedical science [5]. Special attention has been paid to fluorescence responses of metal–terpyridine compounds permitting access to new sensors for bioassays and in vivo imaging purposes [6]. The

Amidofluorene-appended lower rim 1,3-diconjugate of calix[4]arene: synthesis, characterization and highly selective sensor for Cu²⁺

• Rahman Hosseinzadeh,
• Mohammad Nemati,
• Reza Zadmard and
• Maryam Mohadjerani

Beilstein J. Org. Chem. 2016, 12, 1749–1757, doi:10.3762/bjoc.12.163

• supramolecular structures, especially calixarene derivatives, has been an appealing field for research [14]. Calixarene has been considered as an effective molecular scaffold in the improvement of fluorescent and chromogenic sensors, especially for metal-ion recognition [14][15]. Calix[4]arene derivatives having

• different binding centers such as nitrogen, oxygen and sulfur sites for recognition of metal ions can be readily synthesized [14][16][17]. A number of calix[4]arene-based fluorescence sensors for copper ions have been reported in the literature [18][19][20][21][22][23][24][25][26][27], including calix[4

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• our sensor capabilities, with the goal of creating "one well" chemical nose sensors. To this end we expressed ourselves some red, green and blue fluorescent proteins and set to work on cell surface sensing. Rather than going after something easy, we decided to see if we could discriminate mechanisms

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• -carbimino moiety [21] were found to be fluorescence-based sensors of Cu(II) and Mg(II) cations. Considering all above, we decided to synthesize a series of N-substituted derivatives of C-(pyren-1-yl)phosphonoglycine and to investigate their cytotoxic and fluorescence properties. Results and Discussion

Supramolecular chemistry at the interface of biology, materials and medicine

• Eric V. Anslyn and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 1101–1102, doi:10.3762/bjoc.12.105

• ; molecular recognition; molecular sensors; What do art, auto-mechanics, a rural Australian and Chinese village, two civil wars, and house building have to do with supramolecular chemistry? Unless you are an avid cover-to-cover reader of the Thematic Series of the Beilstein Journal of Organic Chemistry and

Indenopyrans – synthesis and photoluminescence properties

• Andreea Petronela Diac,
• Ana-Maria Ţepeş,
• Albert Soran,
• Ion Grosu,
• Anamaria Terec,
• Jean Roncali and
• Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

• context are benzo[b]indeno-[2,1-e]pyran-10,11-diones, which stimulate the biosynthesis of erythropoietin and are used to treat anemia [10]. Another application includes the use of some amino-spiroindenopyran derivatives as selective sensors for thallium(I) ions in human urine [11]. Pyran-containing

• chromophores are valuable candidates for the fabrication of OLEDs [21][22], dye lasers [23], sensors [24], dye-sensitized solar cells, fluorescent probes [25] or logic gates [26]. Recently [27], 6-CF3-2H-pyran-2-ones have been reported as potential building blocks for the preparation of novel

Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins

• Joyeeta Roy,
• Tanushree Mal,
• Supriti Jana and
• Dipakranjan Mal

Beilstein J. Org. Chem. 2016, 12, 531–536, doi:10.3762/bjoc.12.52

• cytotoxic properties [6][7][8][9][10][11]. Anthraquinones are well-known as colorants in foods, drugs, and textile industries. They are also used as chemical sensors and liquid crystals [1][2][3][4][5]. Halogenated anthraquinones form a minor group of natural pigments [12][13][14][15]. 7-Bromoemodic acid (1

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• fluorescent photoinduced electron transfer (PET) pH sensors developed by A. P. De Silva (Figure 3) [17] in order to develop a fluorescence sensor for saccharides [18]. Thus creating a system where the neighbouring nitrogen lowered the working pH of the boronic acid and provided a fluorescence signalling

• system we very quickly went on develop a glucose selective system [28][29] (Figure 5a). It is very rewarding to see that the basic framework of this glucose selective system is still be used by Takeuchi for the development of implantable sensors [30][31][32]. Some moments during your research career can

• visited Beckman-Coulter Inc., Advanced Technology Center in Brea, Orange County, California to discuss a project directed towards the development of fluorescent glucose sensors. Research towards modular systems was started in Birmingham with Susumu Arimori an excellent PDRF from the Shinkai group [53]. My

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

• Inouye and Shinkai [60][61]. IDAs are now one of a handful of standard approaches to creating optical sensors [62]. Our group optimized the citrate receptor design by incorporating a single boronic acid (11) [63] and measured citrate in soda pops [64], vodkas [65], and most recently showed that such

• sugar sensors [43][44][45], and Anthony Czarnik had published his landmark treatise “Desperately Seeking Sensors” [72]. These three individuals are the true fathers of “Supramolecular Analytical Chemistry”, even if our group later introduced this terminology [73]. Sensing a paradigm shift Whereas

• of taste and smell as an approach to chemical sensing seemed obvious. Mammalian chemical sensors do not use highly selective, lock and key-like, receptors, but instead rely on a series of low-selectivity but cross-reactive receptors that create a pattern [83]. These patterns act as fingerprints, to