Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

• Zhihang Bai,
• Krishnasamy Velmurugan,
• Xueqi Tian,
• Minzan Zuo,
• Kaiya Wang and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2022, 18, 429–437, doi:10.3762/bjoc.18.45

• photochemical catalytic reaction in aqueous medium. In addition, our group [30] reported the construction of a supramolecular photocatalytic system with a two-step FRET process through the supramolecular assembly of water-soluble pillar[5]arene and TPE derivatives as donor and EsY and Nile Red (NiR) as

Probing of local polarity in poly(methyl methacrylate) with the charge transfer transition in Nile red

• Aydan Yadigarli,
• Qimeng Song,
• Sergey I. Druzhinin and
• Holger Schönherr

Beilstein J. Org. Chem. 2019, 15, 2552–2562, doi:10.3762/bjoc.15.248

• films on a glass support was probed by the energy of the charge transfer transition in the oxazine dye Nile red (NR) at 25 °C. The absorption and fluorescence spectra of NR were observed to shift to the red with increasing solvent polarity, because of the intramolecular charge transfer character of the

• [1] and segment mobilities inferred [13], respectively. For other purposes the oxazine tracer dye Nile red (NR, Figure 1) served as a local probe to enable the study of degradation of enzyme labile polymersomes [14]. The same dye has been reported as probe for local permittivity in polymers, in

• ., USA) according to published protocols [2][3]. Molecular structure of Nile red (NR). Fluorescence (a) and absorption (b) spectra of NR in solvents of different polarity at 25 °C. The solvent marks are hexane for n-hexane, CHCl3 for chloroform, EtOAc for ethyl acetate, CH2Cl2 for dichloromethane, (CH2Cl

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• derivatives of Nile Red functionalized by a phenol, also grafted to the first and second generation dendrimers (Figure 5). An enhancement of the TPA responses per chromophoric units was observed, but it is less pronounced than for the previous series. Indeed, an increase of TPA of only 20% is obtained for the

• of multistilbazole compounds, and graph of the σ2max/εmax response, depending on the number of fluorophores. Nile Red derivatives: monomer (M) and two generations of dendrimers. Other types of dendrimers having TPA fluorophores as branches and water-solubilizing functions on the surface. Generations

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• . GVs were pelleted down in the Eppendorf tube due to the density difference between the I-solution and the O-solution. The supernatant was carefully removed, and the pellet was re-suspended in 100 µL of fresh O-solution. Each sample was stained with a Nile Red® solution (1 mM in DMSO, 1 µL) before

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• DNA. In addition to TO, other environment-sensitive labels, such as fluorene [168], pyrene [167][169][170], diaminocarbazole [171] and Nile red [172], have been successfully employed in the development of single-labeled fluorogenic aegPNA, γPNA and acpcPNA probes (Figure 18). Up to a 73-fold

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

• functionalization can be achieved upon ligating a triethylsiloxy-functionalized azide and a terminal alkynyl-functionalized luminophore by CuAAC (Cu-catalyzed azide–alkyne cycloaddition) [21][22][23]. Commencing from a 2-hydroxy-substituted Nile red 1 or 3-hydroxymethylperylene (2) the alkyne-substituted

Stimuli-responsive HBPS-g-PDMAEMA and its application as nanocarrier in loading hydrophobic molecules

• Yongsheng Chen,
• Li Wang,
• Haojie Yu,
• Zain-Ul-Abdin,
• Ruoli Sun,
• Guanghui Jing,
• Rongbai Tong and
• Zheng Deng

Beilstein J. Org. Chem. 2016, 12, 939–949, doi:10.3762/bjoc.12.92

• results showed that size of aggregates was affected by a corresponding stimulus. In addition, the loading ability of HBPS-g-PDMAEMA aggregates was investigated by using pyrene or Nile red as the model guest molecules by using UV–vis and fluorescence spectroscopy. The results showed that HBPS-g-PDMAEMA

• to water is a strong evidence for the loading capacity of HBPS-g-PDMAEMA for small hydrophobic molecules. To further confirm the capability of HBPE-g-PDMAEMA aggregates to encapsulate small hydrophobic molecules, Nile red (NR), a commonly used fluorescence dye was used as a model molecule. The

• -PDMAEMA aggregates were capable of encapsulating small hydrophobic molecules. The I3/I1 value reached 0.7 when the polymer concentration was above 2.0 mg/mL. The encapsulation of Nile red showed that HBPS-g-PDMAEMA aggregates are good containers for small hydrophobic molecules. Experimental Materials All

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

• acid dimethyl ester [56]. The obtained polymers formed supramolecular aggregates with diameters between 120 and 250 nm, which were able to encapsulate Nile red (31) that was used as a model of a drug compound (Figure 7). Copolymers containing disulfide groups in the main chain were synthesized from 3,3

Synthesis and optical properties of pyrrolidinyl peptide nucleic acid carrying a clicked Nile red label

• Nattawut Yotapan,
• Chayan Charoenpakdee,
• Pawinee Wathanathavorn,
• Boonsong Ditmangklo,
• Hans-Achim Wagenknecht and
• Tirayut Vilaivan

Beilstein J. Org. Chem. 2014, 10, 2166–2174, doi:10.3762/bjoc.10.224

• , pyrrolidinyl peptide nucleic acid (acpcPNA) was labeled at its backbone with Nile red, a solvatochromic benzophenoxazine dye, by means of click chemistry. The optical properties of the Nile red-labeled acpcPNA were investigated by UV–vis and fluorescence spectroscopy in the absence and in the presence of DNA

• . In contrast to the usual quenching observed in Nile red-labeled DNA, the hybridization with DNA resulted in blue shifting and an enhanced fluorescence regardless of the neighboring bases. More pronounced blue shifts and fluorescence enhancements were observed when the DNA target carried a base

• insertion in close proximity to the Nile red label. The results indicate that the Nile red label is located in a more hydrophobic environment in acpcPNA–DNA duplexes than in the single-stranded acpcPNA. The different fluorescence properties of the acpcPNA hybrids of complementary DNA and DNA carrying a base

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

Diarylethene-modified nucleotides for switching optical properties in DNA

• Sebastian Barrois and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2012, 8, 905–914, doi:10.3762/bjoc.8.103

• we have synthetically attached various chromophores, such as ethynylpyrenes [44][45], BODIPY [46], ethynyl nile red [47][48] and others, to 2’-deoxyuridines for electron transfer studies and for fluorescent probes. To gain greater insight into the counterbase selectivity, we performed PEX experiments

Predicting the UV–vis spectra of oxazine dyes

• Scott Fleming,
• Andrew Mills and
• Tell Tuttle

Beilstein J. Org. Chem. 2011, 7, 432–441, doi:10.3762/bjoc.7.56

• observations by a computational study of the solvatochromism of the oxazine dye Nile red [12]. In the investigation, TD-DFT was applied in order to try and explore the contributing factors in the solvatochromism observed with Nile red, upon gradually increasing the solvent polarity from benzene to acetonitrile

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

Functional properties of metallomesogens modulated by molecular and supramolecular exotic arrangements

• Alessandra Crispini,
• Mauro Ghedini and
• Daniela Pucci

Beilstein J. Org. Chem. 2009, 5, No. 54, doi:10.3762/bjoc.5.54

• prepared in order to expand the applications of these systems towards new peculiar properties induced by innovative cyclometallating and ancillary ligands. For example, an interesting red emitting mesomorphic complex has been prepared starting from the Nile red dye (9-diethylamino-5H-benzo[a]phenoxazine-5

• from their synergy. Molecular structure of NIRPAC: a Pd(II) complex based on Nile red and a curcumin derivative. Molecular structure of Pd(II) complexes based on functionalised 2-phenylquinolines and β-diketonates. Some unusual palladiomesogens based on 3,5-disubstituted-2,2′-pyridylpyrroles and β