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

• derivatives were then selected and their biological and photophysical properties were studied. Luminescent properties of pyrenyl aminophosphonates The widespread use of pyrene derivatives as luminescent probes in biological research [24][25][26][27] prompted us to study emissive properties of the synthesized

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

• Moltech-Anjou, University of Angers, 2 Boulevard Lavoisier 49045 Angers, France 10.3762/bjoc.12.81 Abstract New indeno[1,2-c]pyran-3-ones bearing different substituents at the pyran moiety were synthesized and their photophysical properties were investigated. In solution all compounds were found to be

• groups have been found to exhibit good solvatochromism properties and high quantum yields in the solid state why they are considered as important precursors for the fabrication of fluorescent materials [20]. Owing to their exciting photophysical properties many dicyanomethylene pyran-containing

• of dihydroindeno[1,2-c]pyran-3-ones 2 and 3 as a mixture of isomers (Scheme 1). Additionally, the corresponding phenyl-substituted compounds 2a and 3a (previously reported [30]) were synthesized to investigate the effect of an aryl substituent in position 1 on the photophysical properties of the

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• mesophase of syn-DBBDF 5 was converted to the isotropic phase at 115 °C, while syn-DNBDF 6 did not melt below 250 °C. From the TG measurement, the temperatures of 5% weight loss (Td5) of syn-DBBDF 5 and syn-DNBDF 6 were estimated to be 272 °C and 423 °C, respectively (Figure 2b). Photophysical properties

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• representatives of this class are fluorescein and rhodamine (Figure 1), which have been applied as chemosensors [4] and have been widely exploited in various areas such as cell biology, microscopy, biotechnology, and ophthalmology due to their versatile photophysical properties. However, the chemical modification

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• , several types of permodified CD derivatives, such as 2,3,6-tri-O-methyl-βCD (TM-βCD) or 2,3,6-tri-O-methyl-γCD (TM-γCD) have been synthesized in the course of our investigations. With a view to better understand the influence of TM-βCD and TM-γCD encapsulations on the photophysical properties of PF, poly

• -threaded 3 counterpart, Scheme 1. Results and Discussion In continuation of our interest on the exploration of photophysical properties of PF copolymers by supramolecular encapsulation, we have performed the present study by using liphophylic CD derivatives, such as TM-βCD and TM-γCD instead native β- or

Friedel–Crafts-type reaction of pyrene with diethyl 1-(isothiocyanato)alkylphosphonates. Efficient synthesis of highly fluorescent diethyl 1-(pyrene-1-carboxamido)alkylphosphonates and 1-(pyrene-1-carboxamido)methylphosphonic acid

• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Anna Gajda,
• Tadeusz Gajda,
• Anna Makal,
• Arnaud Brosseau and
• Rémi Métivier

Beilstein J. Org. Chem. 2015, 11, 2451–2458, doi:10.3762/bjoc.11.266

• study along with the photophysical properties of the synthesized 1-(pyrene-1-carboxamido)alkylphosphonates. Results and Discussion Syntheses The reactions performed in this work are shown in Scheme 1. We found that pyrene reacts with isothiocyanates 1a–d in the presence of trifluoromethanesulfonic acid

• isolated in 87% yield. Photophysical properties of 3a–d and 4 As expected, thioamides 2a–d were nonfluorescent (thioamide group is a well-known fluorescence quencher [31]). In contrast, the corresponding amides 3a–d showed strong fluorescence emission in solution and in the solid state. We studied the

• photophysical properties of 3a–d and 4 and, for comparison, those of N-alkylamide 5 (Figure 1). The steady-state spectroscopic data for 3a–d, 4 and 5, along with fluorescence quantum yields in chloroform solutions, are presented in Table 1 (although it was recently reported that pyrene undergoes

2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

• Yury A. Sayapin,
• Inna O. Tupaeva,
• Alexandra A. Kolodina,
• Eugeny A. Gusakov,
• Vitaly N. Komissarov,
• Igor V. Dorogan,
• Nadezhda I. Makarova,
• Anatoly V. Metelitsa,
• Valery V. Tkachev,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2015, 11, 2179–2188, doi:10.3762/bjoc.11.236

• which has attracted much attention due to the applications in various molecular probes and luminescent materials because of the remarkable photophysical properties of the ESIPT (excited state intramolecular proton transfer) chromophores [33][34]. UV-irradiation of solutions of these compounds in

Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2015, 11, 1434–1440, doi:10.3762/bjoc.11.155

• demetalation under acidic conditions to afford the corresponding free-base porphyrins in good to excellent yields. After successful spectroscopic characterization, these porphyrins have been evaluated for their photophysical properties. The preliminary results revealed a bathochromic shift in the UV–vis and

• synthesized and evaluated for their photophysical properties. These compounds have successfully demonstrated the occurrence of an excited electron transfer from the porphyrin subunit to the attached acceptor moieties. On the other hand, some photoinduced electron transfer systems such as porphyrin

A hybrid electron donor comprising cyclopentadithiophene and dithiafulvenyl for dye-sensitized solar cells

• Gleb Sorohhov,
• Chenyi Yi,
• Michael Grätzel,
• Silvio Decurtins and
• Shi-Xia Liu

Beilstein J. Org. Chem. 2015, 11, 1052–1059, doi:10.3762/bjoc.11.118

• conduction band and the dye regeneration, the corresponding electrochemical and photophysical properties were investigated. As depicted in Figure 2, cyclic voltammograms of dyes 1 and 2 in CH2Cl2 show two reversible oxidation waves. To gain additional insight into the redox processes, the cyclic voltammetry

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• Strasbourg, France Institut Universitaire de France, 103 Bd Saint-Michel, 75005 Paris, France 10.3762/bjoc.11.74 Abstract The synthesis and photophysical properties of the first examples of iminosugar clusters based on a BODIPY or a pyrene core are reported. The tri- and tetravalent systems designed as

• fluorophore core is naturally primordial for the design of photostable, water-soluble and biocompatible probes with the required photophysical properties. An additional challenge is that, as the central core of a multivalent system, the fluorophore structure defines also its valency, size and shape

• tetrafunctionalized at the 1, 3, 6 and 8 positions to give a suitable core for the synthesis of tetravalent clusters [53]. In addition, this fluorophore was chosen for its biological/chemical stability and its photophysical properties including high extinction coefficient with reliable fluorescence [54][55]. Another

Efficient deprotection of F-BODIPY derivatives: removal of BF₂ using Brønsted acids

• Mingfeng Yu,
• Joseph K.-H. Wong,
• Cyril Tang,
• Peter Turner,
• Matthew H. Todd and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 37–41, doi:10.3762/bjoc.11.6

• diversifying the F-BODIPY framework [9]. F-BODIPYs are readily prepared by condensing aldehydes, acyl chlorides or anhydrides with pyrroles and trapping the resulting dipyrrin in situ with boron trifluoride [9][10][11]. F-BODIPYs are generally stable and chemically robust, with photophysical properties that

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

• Aurica Farcas,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert,
• Flavian Farcas,
• Iuliana Stoica and
• Anton Airinei

Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

• -dioctylfluorene 3 and compared with those of the corresponding non-rotaxane 4 counterpart. Rotaxane formation results in improvements of the solubility, the thermal stability, and the photophysical properties. Polyrotaxanes 4a and 4b exhibited slightly red-shifted absorption bands with respect to the non-rotaxane

• photophysical properties of PFs we performed the present study. TMS-β-CD and TMS-γ-CD macrocyclic molecules, 1 and 2 monomers, were prepared according to previously reported procedures [13][32][33][34][35]. The chemical structure of completely persilylated compounds was confirmed by using FTIR and NMR

• surfaces. Conclusion The synthesis and photophysical properties of two conjugated polyrotaxanes containing electron-accepting units encapsulated into TMS-β-CD or TMS-γ-CD cavities and electron-donating moieties, statistically distributed into the conjugated chains of 9,9-dioctylfluorene were investigated

Photorelease of phosphates: Mild methods for protecting phosphate derivatives

• Sanjeewa N. Senadheera,
• Abraham L. Yousef and
• Richard S. Givens

Beilstein J. Org. Chem. 2014, 10, 2038–2054, doi:10.3762/bjoc.10.212

• propensity to undergo heterolytic photosolvolysis reactions, most notably o-nitrobenzyl (o-NB) [12], benzyl phenyl ketone (benzoin) [13][14], coumarin-4-ylmethyl [15], and, more recently, p-hydroxyphenacyl (pHP) [15] phosphate esters (Figure 1). While these chromophores exhibit a range of photophysical

• properties, all share a conjugated aromatic structural motif that facilitates UV–vis absorption and serves as a traceless reagents, orthogonal to common ground state deprotection processes and essentially independent of pH effects. Thus, the chromophores are particularly useful at neutral pH and no added

Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity

• Christian B. Winiger,
• Simon M. Langenegger,
• Oleg Khorev and
• Robert Häner

Beilstein J. Org. Chem. 2014, 10, 1589–1595, doi:10.3762/bjoc.10.164

• stability and photophysical properties were investigated. Since the DNA duplex is identical in all hybrids, differences in stability must originate from the modified section. The sequence of the modified part is changed in such a way that annealing of different strands leads to a varying number of pyrene

Multichromophoric sugar for fluorescence photoswitching

• Stéphane Maisonneuve,
• Rémi Métivier,
• Pei Yu,
• Keitaro Nakatani and
• Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

• ), associated with a fluorescence quantum yield ΦF = 0.12. These spectroscopic characteristics are rather comparable to the absorption and fluorescence features of the fluorophore 5 [4]. The photophysical properties of the photochromic model compound 9 have been described in a previous report [4]. Briefly, the

• 610 nm drops back to zero and the fluorescence of the sample is fully recovered (Figure 4c and d). As shown in Figure 4e and f, several UV–visible irradiation cycles were applied to the system without any degradation of its photophysical properties, revealing its excellent fatigue resistance. 1H NMR

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

• Sourav Chakraborty,
• Snehasish Mondal,
• Rina Kumari,
• Sourav Bhowmick,
• Prolay Das and
• Neeladri Das

Beilstein J. Org. Chem. 2014, 10, 1290–1298, doi:10.3762/bjoc.10.130

• multinuclear NMR spectroscopy, mass spectrometry, and elemental analyses techniques. We have also studied the photophysical properties of all triptycene derivatives. Furthermore, we have explored a new face of triptycene-based molecules, viz., interaction of tripodal triptycene-based molecules (with various

On the mechanism of photocatalytic reactions with eosin Y

• Michal Majek,
• Fabiana Filace and
• Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2014, 10, 981–989, doi:10.3762/bjoc.10.97

• -driven reactions that lie beyond the focus of this study. Eosin Y (and many other organic photocatalysts) undergo rapid acid–base equilibria which significantly alter the photophysical properties. It is therefore of pivotal importance to ascertain the actual nature of the employed dye under the reaction

Columnar/herringbone dual crystal packing of pyrenylsumanene and its photophysical properties

• Binod Babu Shrestha,
• Shuhei Higashibayashi and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2014, 10, 841–847, doi:10.3762/bjoc.10.80

• incorporating both bowl and planar structures. Pyrene was selected as the planar substituent when studying solid-state photophysical properties [21][22] and herein we report the columnar/herringbone dual crystal packing of pyrenylsumanene (1) in addition to its photophysical properties. Results and Discussion

First synthesis of meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2014, 10, 808–813, doi:10.3762/bjoc.10.76

• been synthesized and their photophysical properties have not been evaluated yet. By considering the biological and fluorescent properties of these two classes of heterocycles, we envisaged to combine both porphyrin and pyrrolo[1,2-a]quinoxaline units in a single molecular framework to generate novel

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

• Fabian Klukas,
• Alexander Grunwald,
• Franziska Menschel and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

• African trypanosomiasis [18][19][20], and against human renal cancer cells [21][22][23]. Furthermore, 2,5-di(hetero)arylfurans have been reported as photonic chromophores [24]. However, the electronic and photophysical properties of 2,5-di(hetero)aryl furans have only been occasionally studied [25][26][27

• in a one-pot fashion, which opens a ready access to biologically active furan derivatives. In addition the investigation of the photophysical properties of these compounds reveals an intense blue luminescence in solution approaching unity for the fluorescence quantum yield Φf of distinct derivatives

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines

• Christian Muschelknautz,
• Robin Visse,
• Jan Nordmann and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 599–612, doi:10.3762/bjoc.10.51

• -methyl (16a) and an N-tosyl intermediate (16b) clearly shows charge density differences at five distinct atoms (Table 3). All merocyanines 8 and 10 are expectedly deeply colored both in the solid state and in solution. For further investigation of the photophysical properties the absorption spectra were

The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

• Mrinal K. Bera,
• Moisés Domínguez,
• Paul Hommes and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 394–404, doi:10.3762/bjoc.10.37

• light (253 nm) compound 22 shows fluorescence with a maximum intensity at 378 nm (see Supporting Information File 1 for details). The photophysical properties of structurally related pyridine–thiophene conjugates were recently investigated in detail [55][57][58]. Next, we investigated the

Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe

• Matthew B. Plutschack,
• D. Tyler McQuade,
• Giulio Valenti and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 2022–2027, doi:10.3762/bjoc.9.238

• NBDM, enabling us to measure key photophysical properties that will facilitate future uptake studies. Keywords: flow chemistry; fructose mimic; gluts; NBDM; Introduction The impact of dietary fructose on human health is not well-understood. A growing body of work suggests that those eating diets high

• of material. More NBDM is required to examine uptake across many cell lines and with access to amine 3, we can prepare analogues with different fluorophores or other types of tags. Finally, access to more NBDM will enable assessment of probe photophysical properties as a function of concentration and

Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

• Laura Bekere,
• David Gachet,
• Vladimir Lokshin,
• Wladimir Marine and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2013, 9, 1311–1318, doi:10.3762/bjoc.9.147

• . Photophysical properties The spectroscopic properties of 1,8-naphthalimides are strongly dependent on the substituent at C-4 of the naphthalene ring. In general, the derivatives with a halogen atom or alkoxy groups are colorless and exhibit blue fluorecence [15][16], while the amino-substituted 1,8

• detection between 470 and 700 nm in toluene and ethanol. We observed a strong influence of the solvent on the photophysical properties of compound 4. In toluene, at 500 nm (corresponding to the fluorescence maximum), the fluorescence decay followed a mono-exponential law with a lifetime equal to 6.98 ns

Incorporation of perfluorohexyl-functionalised thiophenes into oligofluorene-truxenes: synthesis and physical properties

• Neil Thomson,
• Alexander L. Kanibolotsky,
• Joseph Cameron,
• Tell Tuttle,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2013, 9, 1243–1251, doi:10.3762/bjoc.9.141

• photophysical properties of the resulting oligomer. There are also less common examples of functionalisation at the C3, C8 and C13 positions [9]. Alkyl substituents attached to hetero- and carbocyles, which make up the conjugated backbone of oligomers and polymers, can also affect the properties of the material