Selective detection of DABCO using a supramolecular interconversion as fluorescence reporter

• Indrajit Paul,
• Debabrata Samanta,
• Sudhakar Gaikwad and
• Michael Schmittel

Beilstein J. Org. Chem. 2019, 15, 1371–1378, doi:10.3762/bjoc.15.137

• fluorescence at λ = 602 nm. Ligands, such as pyrazine, 2-chloropyrazine, 1,4-dimethylpiperazine, anthracene, pyrene, coronene, perylene, and perylene-3,4,9,10-tetracarboxylic dianhydride were compared to DABCO. Only in presence of DABCO the fluorescence maximum was shifted to λ = 618 nm along with the color

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• Materials & Engineering (IBME), Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China 10.3762/bjoc.15.117 Abstract The synthesis of conjugates of perylene diimide (PDI) and naphthalene diimide (NDI) modified with two benzo-21-crown-7 ethers (B21C7) are herein described. Their self

• absorption and fluorescence spectra of these PDI/NDI derivatives in different solvents as well as their morphologies were investigated. Keywords: aqueous medium; crown ether; macrocycle; perylene diimide derivative; self-assembly; Introduction Owing to their unique physicochemical properties, self

• with their linear glycol chain counterparts, B21C7 shows great potential to be an easy-to-accessed building block to probe the non-covalent interactions and chemical transformations influenced by water molecules. Perylene diimide (PDI) and naphthalene diimide (NDI) are polycyclic aromatic chromophores

Olefin metathesis in multiblock copolymer synthesis

• Maria L. Gringolts,
• Yulia I. Denisova,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

• functionalized with N-hydroxysuccinate esters (NHS) that can be used as a carrier for antitumor drugs, and the C block is a far-red emitting conjugated random copolymer of p-phenylene ethynylene (PPE) and perylene monoimide (PMI, Figure 2). For the synthesis, the random PPE–PMI copolymer was end-capped with

N-Arylphenothiazines as strong donors for photoredox catalysis – pushing the frontiers of nucleophilic addition of alcohols to alkenes

• Fabienne Speck,
• David Rombach and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 52–59, doi:10.3762/bjoc.15.5

• NHE)) for organic reactions [18]. During the last years, we investigated the photoredox chemistry of new classes of catalysts like perylene bisimides, for their suitability in these types of processes [19] and evaluated the addition of methanol to alkenes as a simple model system. Due to the

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• hydrocarbons [93], heteropolyacenes [90][91], carbazoles [80][81][94], triazines [95], pentacenes [96], diketopyrrolopyrroles [24] and perylene [97][98] derivatives have been investigated as organocatalysts as exemplified in Scheme 5. 3 Comparison of the efficiency of these photoredox catalysts in

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• reduction of aryl halides to the corresponding non-halogenated aromatics. This was extended to the coupling of aryl halides to a variety of substituted pyrroles, using N,N-bis(2,6-diisopropylphenyl)perylene-3,4,9,10-bis(dicarboximide) (PDI) as the photocatalyst, under blue LED irradiation, in DMSO and in

• novel difluoromethylating agent which was used to simultaneously install a difluoromethyl and an acetamide group on various styrene-type derivatives, under perylene-catalysed (Eox* (cat+•/cat) = −2.23 V vs ferrocene in acetonitrile) photoredox conditions (Scheme 14) [57]. For the most part, the scope of

Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

• Cristina Morar,
• Pedro Lameiras,
• Attila Bende,
• Gabriel Katona,
• Emese Gál and
• Mircea Darabantu

Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

• Background: 4-(n-Octyloxy)aniline is a known component in the elaboration of organic materials with mesogenic properties such as N-substituted Schiff bases, perylene bisimide assemblies with a number of 2-amino-4,6-bis[4-(n-octyloxy)phenylamino]-s-triazines, amphiphilic azobenzene-containing linear-dendritic

• (ethynyl)-s-triazine and various icosanyloxyphenylazides) with liquid crystalline and luminescent properties [22]. On the other hand, mesogenic supramolecular perylene bisimide assemblies with a number of 2-amino-4,6-bis[(4-alkoxy)phenylamino]-s-triazines [23], amphiphilic azobenzene-containing linear

A three-armed cryptand with triazine and pyridine units: synthesis, structure and complexation with polycyclic aromatic compounds

• Claudia Lar,
• Adrian Woiczechowski-Pop,
• Attila Bende,
• Ioana Georgeta Grosu,
• Natalia Miklášová,
• Elena Bogdan,
• Niculina Daniela Hădade,
• Anamaria Terec and
• Ion Grosu

Beilstein J. Org. Chem. 2018, 14, 1370–1377, doi:10.3762/bjoc.14.115

• reported cage-box [11] is able to complex a plethora of aromatic compounds (e.g., anthracene, pyrene, perylene), while in the cases of several metallo-based cryptands the formation of layered host–guest supramolecular structures (with many guests in the cavity of the host) were reported [12][13][14][15

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

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

• usage as energy down converting phosphors without employing inorganic transition or rare earth metals is reported in this article. Triethoxysilylpropyl-substituted derivatives of the blue emitting perylene, green emitting benzofurazane, and red emitting Nile red were synthesized and applied in the

• convert the emitted UV light into light with correlated color temperatures of very cold white (41100 K, 10700 K) as well as a greenish white emission with correlated color temperatures of about 5500 K. Keywords: benzofurazane; LED; luminophores; mesoporous silica hybrids; monoliths; Nile red; perylene

• index and tunable color temperature the characteristics of red emissive Nile red, blue emissive perylene, and green emissive benzofurazane have to be matched with comparable emission intensity. All three chromophores exhibit absorption in the UV–vis region with comparable molar absorption coefficients

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

• ][24]. Similar is the case for π-stacking interaction (seen in naphthalene, anthracene, pyrene, perylene, etc.) which has been mostly used in combination with other types of secondary interactions in the discovery of many gelators [25][26]. This holds true for many other non-covalent interactions as

• interactions between the alkyl chains and the triphenylmethyl moieties. Compared to other planar aromatic molecules (such as naphthalene, anthracene, perylene, etc.), the triphenylmethyl moiety as a whole exhibits a non-planar geometry, hence π-stacking interaction between triphenylmethyl moieties may not be

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• known, fluorinated n-type materials are less common [13][30][31]. Nevertheless, fluorinated n-type materials have been shown to exhibit promising characteristics in devices. For instance, the addition of fluorinated groups to naphthalene diimide (NDI) and perylene diimide (PDI) derivatives increased the

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• ), dibenz[a,h]anthracene (dBahANT), indeno[1,2,3-cd]pyrene (IcdPYR) and benzo[g,h,i]perylene (BghiPL); three APs: 4-nonylphenol (4NP, CAS no. 84852-15-3), 4-n-nonylphenol (4nNP, CAS no. 104-40-5) and 4-tert-octylphenol (4tOP, CAS no. 140-66-9). Calcium chloride and sodium bicarbonate were purchased from

Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation

• Martin Weiser,
• Sergej Hermann,
• Alexander Penner and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2015, 11, 568–575, doi:10.3762/bjoc.11.62

• different electron density. Representative mesoflow reactor experiments allowed to significantly shorten the irradiation times and to use sunlight as “green” light source. Keywords: electron transfer; perylene bisimide; photocatalysis; photochemistry; pyrene; Introduction Photocatalysts are organic or

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• carboxylates affords compounds 33a–c in moderate to good yields, whereas the reaction with NaN3 provided the ω,ω’-diazide 34. The latter compound served as interface for labelling with various alkyne-functionalized compounds. As proof-of-concept we successfully coupled 34 with the perylene derivative 35 to

Lateral ordering of PTCDA on the clean and the oxygen pre-covered Cu(100) surface investigated by scanning tunneling microscopy and low energy electron diffraction

• Stefan Gärtner,
• Benjamin Fiedler,
• Oliver Bauer,
• Antonela Marele and
• Moritz M. Sokolowski

Beilstein J. Org. Chem. 2014, 10, 2055–2064, doi:10.3762/bjoc.10.213

• , 76131 Karlsruhe, Germany Departamento de Física de la Materia Condensada, Universidad Autónoma de Madrid, 28049, Madrid, Spain 10.3762/bjoc.10.213 Abstract We have investigated the adsorption of perylene-3,4,9,10-tetracarboxylic acid dianhydride (PTCDA) on the clean and on the oxygen pre-covered Cu(100

• light-emitting diodes [2]. In order to obtain a fundamental understanding of the interactions at these interfaces, the adsorption of perylene-3,4,9,10-tetracarboxylic acid dianhydride (PTCDA) on single crystal surfaces of noble metals has been studied intensively as a model system [3]. On the coinage

• anhydride groups and the positively charged perylene cores. On Cu(100) the area per molecule corresponds to 131.2 Å2. This value is very comparable to that for PTCDA on Ag(100) (132.9 Å2). Both values are about 10% larger than the area per molecule in the lattice planes of PTCDA bulk crystals of the α or β

Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization

• Jacques Lalevée,
• Sofia Telitel,
• Pu Xiao,
• Marc Lepeltier,
• Frédéric Dumur,
• Fabrice Morlet-Savary,
• Didier Gigmes and
• Jean-Pierre Fouassier

Beilstein J. Org. Chem. 2014, 10, 863–876, doi:10.3762/bjoc.10.83

• , potential toxicity and limited availability of these structures, metal-free organic dye compounds (e.g., Eosin-Y, Nile Red, Alizarine Red S, perylene derivative or Rhodamine B etc.) were recently proposed for cooperative asymmetric organophotoredox catalysis [13][14]. Photoredox catalysis was then

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

Synthesis and characterization of low-molecular-weight π-conjugated polymers covered by persilylated β-cyclodextrin

• Aurica Farcas,
• Ana-Maria Resmerita,
• Andreea Stefanache,
• Mihaela Balan and
• Valeria Harabagiu

Beilstein J. Org. Chem. 2012, 8, 1505–1514, doi:10.3762/bjoc.8.170

• the absorption and fluorescence excitation spectra shows that major structural changes have not occurred, and that emissions arose from the compounds and not from the thienyl end-capping, as has been previously reported for PFO with perylene derivative as end-units [35]. Conclusion The present study

Self-assembly and semiconductivity of an oligothiophene supergelator

• Pampa Pratihar,
• Suhrit Ghosh,
• Vladimir Stepanenko,
• Sameer Patwardhan,
• Ferdinand C. Grozema,
• Laurens D. A. Siebbeles and
• Frank Würthner

Beilstein J. Org. Chem. 2010, 6, 1070–1078, doi:10.3762/bjoc.6.122

• these elongated fibres form interpenetrating network in which the solvent molecules are trapped [3][4]. Organogels based on various π-systems such as oligophenylenevinylenes [5] and thienylenevinylenes [6] oligophenyleneethylenes [7], phthalocyanines [8], porphyrins [9], naphthalene and perylene

• ability of quaterthiophene and hexathiophene derivatives with peripheral amide-linked cholesterol moieties [19]. We recently reported [12] the self-assembly of perylene bisimide (PBI) π-systems that are functionalized with trialkoxybenzamide moiety and have shown that they possess much superior and

• of donor and acceptor materials plays a prominent role in device performance [25]. Recently, we reported that a n-type perylene bisimide organogelator exhibits photovoltaic activity with a p-type semiconducting polymer [26]. In this work, as an initial study we characterized the morphology of a

Synthetic incorporation of Nile Blue into DNA using 2′-deoxyriboside substitutes: Representative comparison of (R)- and (S)-aminopropanediol as an acyclic linker

• Daniel Lachmann,
• Sina Berndl,
• Otto S. Wolfbeis and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2010, 6, No. 13, doi:10.3762/bjoc.6.13

• nucleic acids (TINA) [27][28], and by our group for fluorescent DNA base substitutions by ethidium [29][30], indole [31][32], thiazole orange [33][34], perylene bisimide [35][36] and phenothiazine [37]. This 2′-deoxyriboside substitution provides high chemical stability and conformational flexibility for

Synthesis and redox behavior of new ferrocene- π-extended- dithiafulvalenes: An approach for anticipated organic conductors

• Abdelwareth A. O. Sarhan,
• Omar F. Mohammed and
• Taeko Izumi

Beilstein J. Org. Chem. 2009, 5, No. 6, doi:10.3762/bjoc.5.6

• characterized a donor-acceptor dyad system involving tetrathiafulvalene (TTF) as electron donor attached by a flexible spacer to perylene derivatives as electron acceptor [5]. They have shown that the fluorescence of the tetrathiafulvalene–perylene derived dyad can be reversibly modulated by the transformation