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

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• entrance via confocal laser scanning microscopy [30]. Several types of dye moiety/CD derivatives have been suggested as "switch on" or "switch off" fluorescent chemical sensors. In these systems, the complexation with a guest molecule allows to enhance or decrease the fluorescence intensity. Two water

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• field of supramolecular chemistry, specifically, and organic materials, broadly. My research group’s efforts toward designing new sensors based on small molecule gelators are described. In particular, I highlight how our design strategy has evolved as we learn more about molecular gelators. This

• inspired by the creative work of many researchers in the field at the time [21][22][23][24]. When it came time to assemble a set of job proposals, it seemed natural for one focused on molecular gelation. Specifically, I proposed to develop sensors wherein a chemical stimulus (analyte) reacts with a “latent

• gelator” and induces gelation (Figure 2). Gel-based sensors were appealing because they provide an unambiguous visual change in the material’s physical properties with no interference from colored or opaque samples. Moreover, no instrumentation or training is necessary to interpret the results, thereby

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

• Sophie Letort,
• Sébastien Balieu,
• William Erb,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

• organophosphorus compounds, CDs have gained a significant attention for a variety of applications such as sensors for detection [31][32] or materials for nerve agents decontamination [33]. Various analytical methods exist to monitor the NOPs exposure [34][35][36]. However, these are long, expensive, required

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• ], chemical sensors [6] and drug delivery [7][8][9]. As discussed in a range of reviews [10][11][12][13][14] and books [15][16][17][18], cyclodextrins are naturally occurring cyclic oligosaccharides which are also produced industrially through the enzymatic metabolism of starch and related compounds. The

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

• miniature information processor, e.g., a logic gate [16][19][20][21]. Indeed, molecular sensors and logic gates are related in several ways [16]. Both of them are rooted in two (or higher) -state equilibria between free and bound forms of a molecule, so that sensors become the simplest logic gates. However

• design tool has been taken up by about 330 laboratories (Figure 1, PET maps) so far. A bit of medical diagnostics While it was clear from the beginning that fluorescent PET sensors would be useful, we saw no practical path to such development. Serendipity had to smile in the form of the interest and the

• instances where fluorescent PET sensors are immobilized on the tips of optic fibres placed in a vein, to allow continuous monitoring of blood. Glucose monitoring [44][45] is one such success [46]. Problems of white cell attack and subsequent covering up of the fibre tip, which frustrated previous

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• sensors. This was surprising, as the fluorophores are small molecules attached to the termini of much larger DNA molecules. However, we found this lesson very informative, as it showed that dyes and other functional groups that we frequently append to DNA are not as innocuous as we assume them to be

• . Rather, they can have a dramatic impact on the assembly properties of the DNA sequences. In our experiments, this was particularly noticeable, as the structure-switching sensors are tuned to have an equilibrium near unity, which allows small amounts of the target to trigger displacement. Thus, in these

• and electrostatic properties, and we found that they provided enantiomeric sensors having nearly identical equilibrium constants. To test our enantiopurity analysis method, the two biosensors were incubated together with varying ratios of L- and D-Tym to construct calibration curves relating the

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• electrochemistry [18] or by adding an oxidizing agent [19]. Different studies have employed this concept to form redox-responsive systems applied, for example, in self-healing materials [19], polymeric hydrogels [20][21], voltage-responsive vesicles [22], ultrasentive enzyme sensors [23], and as a plasma membrane

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

• functional dyes [22][23]. Furthermore, various multifunctional TTF-based supramolecular architectures have been designed and synthesized to realize molecular sensors, redox switches, multi-input systems for logic gates, electrochemically-driven conformational controls, molecular clips and tweezers, and redox

• realize electrochemically-driven conformational control, redox-controlled gelation processes, redox switches, and molecular sensors. Furthermore, semiconductive fibers and rods of TTFs can be utilized for nanosized electric wires and wirings in nanoelectronics. The next key innovation in TTF-based

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• and the fluorescence was quenched. Therefore, it was proposed that the films can be used as sensors for these explosives. Frampton et al. synthesised a polyester from the dimethyl ester of 1,3-bis(3-carboxypropyl)-1,1,3,3-tetramethyldisiloxane and 1,3-bis(3-hydroxypropyl)-1,1,3,3-tetramethyldisiloxane

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