Synthetic mRNA capping

• Fabian Muttach,
• Nils Muthmann and
• Andrea Rentmeister

Beilstein J. Org. Chem. 2017, 13, 2819–2832, doi:10.3762/bjoc.13.274

• dyes which could be applied as FRET pair. In this case, labeling was achieved in two bioorthogonal reactions, an iEDDA and a SPAAC reaction. Furthermore, dual modification with an azido and an alkyne function enabled fluorophore/biotin labeling using a combination of SPAAC and CuAAC reaction. Efficient

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

• characterized environment-dependent fluorescence. This property, together with the facile synthetic accessibility, makes it and its derivatives useful for a number of applications, e.g., as materials for organic electronics [1], dyes for mechanochromic materials [2], and fluorescent monomers for polymer

• MitoTracker Red®, an established fluorescent mitochondrial marker (Figure 6BC and Figure 7BC, respectively). To quantify the co-localization of 4 and 5 dyes and MitoTracker Red® the Manders (MCC) and Pearson (PCC) correlation coefficient were used [37]. The calculated values of MCC were 0.83 ± 0.12 (for 4

• in deionized water. The dyes were added in 1 to 3 equivalent steps compared to the concentration of the template strand. The percentage of DMSO changed with every addition up to a maximum of about 5% in the sample solution, so the DMSO was neglected in the blank subtraction. To achieve a good

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

• Jan Podlesný,
• Lenka Dokládalová,
• Oldřich Pytela,
• Adam Urbanec,
• Milan Klikar,
• Numan Almonasy,
• Tomáš Mikysek,
• Jaroslav Jedryka,
• Iwan V. Kityk and
• Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

• pigments [2], DPPs have significantly infiltrated organic electronics as functional dyes. The number of recently appeared review articles [3][4][5][6][7][8] clearly demonstrates their wide application potential, which spans organic solar cells (OSC), organic field-effect transistors (OFET), organic light

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

• Phthalocyanines and subphthalocyanines are attracting attention as functional dyes that are applicable to organic solar cells, photodynamic therapy, organic electronic devices, and other applications. However, phthalocyanines are generally difficult to handle due to their strong ability to aggregate, so this

• years, the term “functional dyes” was proposed [9][10][11]. Functional dye is a generic name for dyes that exceed the framework of coloration and show various chemical and physical responses. In modern times, unlike the concept of colorants in the past, dyes have been developed for various applications

• based on their unique functions. Phthalocyanines are also expected to be applied as functional dyes. A series of compounds having a macrocyclic π-conjugated system including porphyrin are known as functional dyes. In particular, phthalocyanines have a wide range of functions and are expected to serve as

Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

• Henning Weiss,
• Jeannine Reichel,
• Helmar Görls,
• Kilian Rolf Anton Schneider,
• Mathias Micheel,
• Michael Pröhl,
• Michael Gottschaldt,
• Benjamin Dietzek and
• Wolfgang Weigand

Beilstein J. Org. Chem. 2017, 13, 2264–2272, doi:10.3762/bjoc.13.223

• .13.223 Abstract Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been

• investigated. Furthermore, a strategy for the hydrolysis of the BF2 group has been established using aqueous methanol and sodium hydroxide or triethylamine. Keywords: BF2 complex; curcumin; dyes; fluorescence; hydrolysis; spectroscopy; Introduction In recent years curcumin, a pigment naturally occurring in

• attention regarding their properties as fluorescent dyes with fluorescence quantum yields of up to 60% and Stokes shifts of up to 5000 cm−1 [9]. Additionally, the incorporation of the BF2 group forces the β-diketone unit into the enol form, which leads to increased rigidity and enhanced photostability of

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

• substituted benzyl alcohols. Although benzyl alcohol is industrially produced by reduction of benzaldehyde, this aldehyde is considered as the second most important flavoring molecule after vanillin, due to its variety of applications in cosmetics, perfumes, food, dyes, agrochemicals and pharmaceuticals [41

β-Cyclodextrin- and adamantyl-substituted poly(acrylate) self-assembling aqueous networks designed for controlled complexation and release of small molecules

• Liang Yan,
• Duc-Truc Pham,
• Philip Clements,
• Stephen F. Lincoln,
• Jie Wang,
• Xuhong Guo and
• Christopher J. Easton

Beilstein J. Org. Chem. 2017, 13, 1879–1892, doi:10.3762/bjoc.13.183

• substituted poly(acrylate)s, PAAADen, PAAADhn and PAAADddn, respectively, such that the ratio of β-CDen to adamantyl substituents is ca. 3:1. The variation of the characteristics of the complexation of the dyes methyl red, methyl orange and ethyl orange in these three networks and by β-cyclodextrin, β-CD, and

• PAAβ-CDen alone provides insight into the factors affecting dye complexation. The rates of release of the dyes through a dialysis membrane from the three aqueous networks show a high dependence on host–guest complexation between the β-CDen substituents and the dyes as well as the structure and the

• substitution of PAAβ-CDen. Thus, when host–guest complexation between the poly(acrylate) substituents of the network is complete, ca. two thirds of the β-CDen substituents remain available to complex other hydrophobic species exemplified by the dyes methyl red, MR, methyl orange, MO, and ethyl orange, EO

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

• Santanu Hati,
• Ulrike Holzgrabe and
• Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

• an important class of compounds [1]. A large variety of such compounds are discovered so far and their therapeutic potential in diverse disease models has been thoroughly investigated [2]. For example thiazoles and oxazoles are found in various bioactive natural products, organic dyes and

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

• Roman A. Irgashev,
• Nikita A. Kazin,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

• -dihydroindolo[3,2-b]carbazole (indolo[3,2-b]carbazole, ICZ) has been successfully used as a basic structural fragment of perspective electroluminescent, hole-transporting materials and light-harvesting dyes for organic light emitting diodes (OLEDs) [7][8][9][10][11][12][13], organic field-effect transistors

Detection of therapeutic radiation in three-dimensions

• John A. Adamovics

Beilstein J. Org. Chem. 2017, 13, 1325–1331, doi:10.3762/bjoc.13.129

• leuco dye, which is radiolytically oxidized to a dye absorbing at 630 nm. Keywords: dosimeters; leuco dyes; polymers; radiation; triarylmethane synthesis; Introduction Radiotherapy treatment is a complex 3D process, which is the principle treatment modality for most cancers [1]. The two main types of

• dosimeter would be firm in structure and tissue equivalent [14]. This review describes such a 3D dosimeter, which we have been studying since 2004, composed primarily of the polymer polyurethane containing a radiochromic leuco dye and a radical initiator [15]. Review Leuco dyes and radical initiators Our

• initial studies focused on a broad class of compounds referred to as leuco dyes which switch between two chemical forms of which one is colorless. The transformations are caused by the in put of energy either from heat, light or change in pH [16]. The leuco dyes by themselves are not oxidized at clinical

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• , sensitivity and good spatio-temporal resolution altogether [5]. From the plethora of known fluorescent compounds, there are widely used small organic fluorophores, such as BODIPY dyes. BODIPYs are fluorescent dyes based on the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene scaffold, which have recently

• experienced increased attention in chemistry [6][7][8][9][10] and life science applications [11][12][13]. On the grounds of high fluorescence quantum yield, narrow spectral characteristics, and sufficient chemical stability, BODIPYs have been utilized for example as laser dyes, tags of small organic molecules

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• diameter range can be obtained [4]. Moreover, this synthetic procedure allows to introduce different types of carbohydrates and other ligands (i.e., polyethylene chains, lipids, peptides, DNA, RNA or fluorescent dyes) in controlled ratios [4]. A modification of this technique consists in the application of

Synthesis of tetrasubstituted pyrazoles containing pyridinyl substituents

• Josef Jansa,
• Ramona Schmidt,
• Ashenafi Damtew Mamuye,
• Laura Castoldi,
• Alexander Roller,
• Vittorio Pace and
• Wolfgang Holzer

Beilstein J. Org. Chem. 2017, 13, 895–902, doi:10.3762/bjoc.13.90

• ], agrochemicals [5], dyes [6], fluorescent materials [7][8] and ligands of complexing agents [9][10][11]. Multiaryl-substituted pyrazoles are of special interest, with some drug molecules such as the nonsteroidal anti-inflammatory agent Lonazolac [12] or the well-known COX-2 inhibitor Celecoxib [13] as prominent

Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes

• Markus Börgardts and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 768–778, doi:10.3762/bjoc.13.76

• molecules with inorganic silica hosts [11][20]. Therefore, a terminal triethoxysilyl group has to be coupled to luminescent dyes with blue, green, and red emission characteristics for generating hybrid materials with white light emission based upon additive color mixing. A rapid and versatile

• (Figure 1a). Neglecting energy transfer between the luminophores superposition of the emission spectra of the three dyes covers the whole range of the visible region (400–800 nm) (Figure 1b). The three dyes were additionally analyzed with respect to their CIE chromaticity coordinates, i.e., their

• attributed to an inhomogeneous line broadening in the solid state. As benzofurazane and Nile red dyes exhibit solvatochomism, their spectral properties are clearly affected by incorporation into the polar silica environment. A detailed study of the spectral properties and solvatochromism of the Nile red

Isoxazole derivatives as new nitric oxide elicitors in plants

• Anca Oancea,
• Emilian Georgescu,
• Florentina Georgescu,
• Alina Nicolescu,
• Elena Iulia Oprita,
• Catalina Tudora,
• Lucian Vladulescu,
• Marius-Constantin Vladulescu,
• Florin Oancea and
• Calin Deleanu

Beilstein J. Org. Chem. 2017, 13, 659–664, doi:10.3762/bjoc.13.65

• -disubstituted isoxazoles on nitric oxide and reactive oxygen species generation in Arabidopsis tissues was studied using specific diaminofluoresceine dyes as fluorescence indicators. Keywords: chemical elicitor; 1,3-dipolar cycloaddition; isoxazole; nitric oxide; nitrile oxide; reactive oxygen species

N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• kinase activity [10][11][12][13][14] (Figure 1). This compound class is also a crucial part of many natural products such as vitamin B1 (thiamine), epothilone, dolastatin, and many more (Figure 2) [15][16][17][18][19][20][21][22][23][24]. Moreover, thiazoles are widely applied as pesticides and dyes [25

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• /bjoc.13.52 Abstract Eosin B (EoB) and eosin Y (EoY), two xanthene dye derivatives with photosensitizing ability were prepared in high purity through an improved synthetic route. The dyes were grafted to a 6-monoamino-β-cyclodextrin scaffold under mild reaction conditions through a stable amide linkage

• xanthene-type PSs in conjugation with CDs is very scarce. The reasons behind this fact are most probably the difficulties in selective CD functionalization and limitations in xanthene-dye modification. Xanthene dyes can be introduced into the CD scaffold most easily through an ester linkage between the

• -β-CD scaffold was achieved through amide-bond formation between the amino-CD and the carboxylic group of the xanthene dyes [26]. This strategy does not require the laborious isothiocyanate functionalization and it can be applied to all xanthene dyes having a carboxylic function. Encouraged by these

Investigation of the action of poly(ADP-ribose)-synthesising enzymes on NAD⁺ analogues

• Sarah Wallrodt,
• Edward L. Simpson and
• Andreas Marx

Beilstein J. Org. Chem. 2017, 13, 495–501, doi:10.3762/bjoc.13.49

• introducing small, terminal alkyne functionalities at common sites of the adenine base. Upon successful incorporation into PAR, these alkynes serve as handles for copper(I) catalysed azide–alkyne click reaction (CuAAC) [22] with fluorescent dyes. Terminal alkynes are the smallest possible reporter group that

Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state

• Jonas Becher,
• Daria V. Berdnikova,
• Darinka Dzubiel,
• Heiko Ihmels and
• Phil M. Pithan

Beilstein J. Org. Chem. 2017, 13, 203–212, doi:10.3762/bjoc.13.23

• ] hosts with high affinity [6]. In most cases, this complexation strongly affects the chemical or physical properties of the ligand. For example, it was demonstrated that the optical properties of organic dyes may be modified drastically upon complexation in the CB cavity [7]. At the same time, this

• ]. Notably, the chromophore of the oxyanion-substituted quinolizinium derivative 2cB resembles the well-established solvatochromic pyridinium-N-phenolate betaine dyes that are employed as polarity probes [53]. Correspondingly, the derivative 2cB shows a similar positive solvatochromism, i.e., a blue shift of

• their versatility as functional dyes. Experimental General The employed fine chemicals (Sigma-Aldrich, Acros or Alfa Aesar) were reagent grade and used without further purification. NMR spectroscopy: Bruker Avance 400 (1H: 400 MHz, 13C: 100 MHz) or Varian VNMR-S 600 (1H: 600 MHz, 13C: 150 MHz); at 25 °C

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• linear molecular arrays and also between two-dimensional planar arrays. The weak intensity peak at 22.39° (3.96 Å) can be attributed to the presence of π–π stacking between benzene rings of adjacent triphenylmethyl groups. Dye absorption studies Dyes are commercially important and are widely used in many

• industries. But most of these dyes are toxic and harmful to the environment. Discharge of waste water generated during use of these water-soluble dyes without proper pretreatment creates a serious environmental and health hazard. Hence, development of simple and reliable methods to remove dyes from the

• industrial waste water is becoming increasingly important. Conventionally, this has been achieved through the use of materials like clay, porous silica, polymers, charcoals, etc. [37]. More recently, some gels derived from low molecular weight compounds have been shown to possess the ability to absorb dyes

A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA

• Heidi-Kristin Walter,
• Bettina Olshausen,
• Ute Schepers and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16

• by blue and green emitting cyanine-styryl dyes were improved due to the arabino-configured anchor. These oligonucleotides were used as energy transfer donors in hybrids with oligonucleotides modified with acceptor dyes that emit in the yellow-red range. These combinations give energy transfer pairs

• yield. Especially mixed combinations, that means donor dyes with arabino-configured anchor with acceptor dyes with ribo-configured anchor, and vice versa, showed significantly improved fluorescence properties. Those were successfully applied for fluorescent imaging of DNA after transport into living

• cells. Keywords: dyes; fluorescence; nucleic acid; oligonucleotide; Introduction The “click”-type reactions [1], in particular the 1,3-dipolar cycloaddition between alkynes and azides (CuAAC) is a broadly applied strategy for postsynthetic oligonucleotide modification since both reactive groups are

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• solution the rate of decomposition was lower partly attributed to adsorption of chloride on TiO2 surface. There might be a competition between dyes and anions for the adsorption sites and the anions may modify the superficial properties of TiO2 [44]. The total concentration of inorganic ions in tap water

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

• Lukas J. Patalag and
• Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

• methods are commonly employed. Either unnatural fluorescent dyes are inserted into the membrane (e.g., pyrene) or the hydrophilic part of lipids is utilized for the covalent attachment of fluorophores. Another possibility is the use of fluorescently labelled antibodies which bind membrane components such