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Search for "circular dichroism" in Full Text gives 132 result(s) in Beilstein Journal of Organic Chemistry.

Multicomponent reactions in nucleoside chemistry

  • Mariola Koszytkowska-Stawińska and
  • Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

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  • %. The diastereoisomers were separated and their absolute configuration was determined using X-ray crystallography and circular dichroism spectroscopy. The stereochemical outcome of the synthesis of compounds 79 and 80 was suggested to result from some internal asymmetric induction of the chiral residue
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Published 29 Jul 2014

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

  • Silvia Bernardi,
  • Paola Fezzardi,
  • Gabriele Rispoli,
  • Stefania E. Sestito,
  • Francesco Peri,
  • Francesco Sansone and
  • Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

Graphical Abstract
  • -tagged full-length Gal-3 was expressed in E. coli BL21 and purified on IMAC (immobilized metal ion affinity chromatography) columns. Purified protein was characterized by SDS-PAGE electrophoresis, circular dichroism (CD), and MS/MS analysis upon digestion on trypsin gel (see Figure S15, Supporting
  • /glycocalixarene binding experiments), 1H NMR spectra of selected intermediates, and final glycocalixarenes 1–4 together with electrophoresis gel, circular dichroism spectrum and thermal unfolding of purified Gal-3. Supporting Information File 610: Experimental part. Acknowledgements The authors gratefully
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Published 23 Jul 2014

Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60

  • Marco Caricato,
  • Silvia Díez González,
  • Idoia Arandia Ariño and
  • Dario Pasini

Beilstein J. Org. Chem. 2014, 10, 1308–1316, doi:10.3762/bjoc.10.132

Graphical Abstract
  • , Supporting Information File 1) show the major absorption band centered around 230 nm, typical of the binaphthyl chromophore [41]. Circular dichroism spectroscopy of the same macrocycles show the exciton couplet typical of binaphthyl moieties (Figure 3), corresponding to the maximum absorption band in the UV
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Published 06 Jun 2014

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

  • Zbigniew Pakulski,
  • Norbert Gajda,
  • Magdalena Jawiczuk,
  • Jadwiga Frelek,
  • Piotr Cmoch and
  • Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

Graphical Abstract
  • oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology. Keywords: CD-spectroscopy; Cotton effect; multivalent glycosystems; osmylation; stereoselective
  • circular dichroism spectroscopy (CD) using the in situ dimolybdenum methodology (see next chapter). Next steps of the synthesis consisted of the protection of the C6–OH as benzyl ether (to 12) and osmylation of the double bond. The cis-dihydroxylation provided, as single stereoisomer, a diol to which
  • surprising. The assignment of the configuration of this diol was further confirmed also by the CD methodology; this is discussed in the next chapter. Determination of the absolute configuration of 11 and 13 It is widely acceptable that the circular dichroism (CD) spectroscopy utilizing the in situ
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Published 28 May 2014

cistrans Isomerization of silybins A and B

  • Michaela Novotná,
  • Radek Gažák,
  • David Biedermann,
  • Florent Di Meo,
  • Petr Marhol,
  • Marek Kuzma,
  • Lucie Bednárová,
  • Kateřina Fuksová,
  • Patrick Trouillas and
  • Vladimír Křen

Beilstein J. Org. Chem. 2014, 10, 1047–1063, doi:10.3762/bjoc.10.105

Graphical Abstract
  • optically pure compounds was determined by using NMR and comparing their electronic circular dichroism data with model compounds of known absolute configurations. Mechanisms for cis–trans-isomerization of silybin are proposed and supported by quantum mechanical calculations. Keywords: 2,3-cis-silybin
  • -cis-10,11-trans-isomer 12 and a minor 23-O-acetyl-2,3-trans-10,11-cis-isomer 13 (Scheme 3). Surprisingly, the absolute configuration at C-2, C-3 of compound 13 was the opposite of 1a (2S,3S vs 2R,3R), which was confirmed by a comparison of their electronic circular dichroism (ECD) data. Formation of
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Published 08 May 2014

A new building block for DNA network formation by self-assembly and polymerase chain reaction

  • Holger Bußkamp,
  • Sascha Keller,
  • Marta Robotta,
  • Malte Drescher and
  • Andreas Marx

Beilstein J. Org. Chem. 2014, 10, 1037–1046, doi:10.3762/bjoc.10.104

Graphical Abstract
  • circular dichroism (CD) spectroscopy. The CD spectra of Y-shaped bDNA ODN I bound to oligonucleotides 8–11, respectively, show dichroic peaks similar to those of unmodified DNA duplexes, indicating that bDNA maintain the B-DNA form (see Supporting Information File 1). As the Y-shaped bDNA is able to
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Published 07 May 2014

Decandrinin, an unprecedented C9-spiro-fused 7,8-seco-ent-abietane from the Godavari mangrove Ceriops decandra

  • Hui Wang,
  • Min-Yi Li,
  • Félix Zongwe Katele,
  • Tirumani Satyanandamurty,
  • Jun Wu and
  • Gerhard Bringmann

Beilstein J. Org. Chem. 2014, 10, 276–281, doi:10.3762/bjoc.10.23

Graphical Abstract
  • , Ceriops decandra, collected in the estuary of Godavari, Andhra Pradesh. The constitution and the relative configuration of 1 were determined by HRMS (ESI) and extensive NMR investigations, and the absolute configuration by circular dichroism (CD) and optical-rotatory dispersion (ORD) spectroscopy in
  • combination with quantum-chemical calculations. Decandrinin is the first 7,8-seco-ent-abietane. Keywords: abietane; absolute configuration; Ceriops decandra; circular dichroism; decandrinin; Rhizophoraceae; Introduction Ceriops decandra is a mangrove of the family Rhizophoraceae. It is widely distributed
  • NMR investigations, and by circular dichroism (CD) and optical-rotatory dispersion (ORD) spectroscopy in combination with quantum-chemical calculations. Results and Discussion Decandrinin (1) was obtained as a colorless solid. Its molecular formula was established as C20H28O4 by HRMS (ESI) (m/z
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Published 27 Jan 2014

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

  • Jun Hu,
  • Jindan Wu,
  • Qian Wang and
  • Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

Graphical Abstract
  • in the formation of CT gels is demonstrated through the formation of gels in a variety of solvents. Thermal stability, stoichiometry, scanning electron microscopy (SEM), optical micrographs, and circular dichroism (CD) are performed on these CT gels to investigate their thermal and assembly
  • reported to aggregate in both forms, right-handed and left-handed helices in equal proportions [57][58]. Therefore, circular dichroism (CD) was used to investigate the chirality of these CT gels and sol. The results showed a strong negative signal around 430 nm and a positive signal around 550 nm
  • Finnigan TSQ spectrometer in positive mode; circular dichroism spectra were performed on JASCO J-815 CD spectrometer; scanning electron microscopy (SEM) images were performed on a Variable Pressure Tescan Vega3 SBU; optical micrographs were performed on a Olympus CKX41 microscope. Samples for optical
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Published 16 Dec 2013

Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

  • Holger Erdbrink,
  • Elisabeth K. Nyakatura,
  • Susanne Huhmann,
  • Ulla I. M. Gerling,
  • Dieter Lentz,
  • Beate Koksch and
  • Constantin Czekelius

Beilstein J. Org. Chem. 2013, 9, 2009–2014, doi:10.3762/bjoc.9.236

Graphical Abstract
  • peptide (KX), its α-helix propensity can be calculated from circular dichroism (CD) spectroscopy [8][9]. Therefore, 5-F3Ile was converted into its Fmoc analogue and subsequently used in solid-phase synthesis of K-5-F3Ile applying standard Fmoc-based chemistry (see Supporting Information File 1) [30]. The
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Published 02 Oct 2013

Self-assembly of 2,3-dihydroxycholestane steroids into supramolecular organogels as a soft template for the in-situ generation of silicate nanomaterials

  • Valeria C. Edelsztein,
  • Andrea S. Mac Cormack,
  • Matías Ciarlantini and
  • Pablo H. Di Chenna

Beilstein J. Org. Chem. 2013, 9, 1826–1836, doi:10.3762/bjoc.9.213

Graphical Abstract
  • to n-hexane and dichloromethane xerogels. This is indicative of a more compact assembly in this polar solvent. Due to the lack of a chromophore in 1, it was not possible to use circular dichroism to prove the helicoidal nature of the fibrillar network, but images suggest that, at least in
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Published 09 Sep 2013

Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

  • M. B. Avinash,
  • K. V. Sandeepa and
  • T. Govindaraju

Beilstein J. Org. Chem. 2013, 9, 1565–1571, doi:10.3762/bjoc.9.178

Graphical Abstract
  • ). In order to gain further insights into the nature of molecular interactions, 1, 2 and 3 were subjected to circular dichroism (CD) spectroscopic studies. The CD spectra of 1 in DMSO show positive excitonic cotton effects, indicating a P-type helical assembly (Figure 3a). However, with increase in the
  • -21G basis set) to get additional insights about their conformations (Figure 5a, 5b). After careful evaluation of absorption, fluorescence, circular dichroism, NMR as well as PXRD data, the plausible molecular stacking model depicting the charge-transfer complexation under enhanced hydrophobic forces
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Published 01 Aug 2013

Linkage of α-cyclodextrin-terminated poly(dimethylsiloxanes) by inclusion of quasi bifunctional ferrocene

  • Helmut Ritter,
  • Berit Knudsen and
  • Valerij Durnev

Beilstein J. Org. Chem. 2013, 9, 1278–1284, doi:10.3762/bjoc.9.144

Graphical Abstract
  • by circular dichroism spectroscopy [8] and thermogravimetric analysis [9]. In addition, the complex of ferrocene and α-CD could be detected in the gas phase by mass spectrometry [10]. Recently, there have been many reports focusing on the use of α-CD in aqueous solution as a mobile phase for optical
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Published 01 Jul 2013

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

  • Dyanne L. Cruickshank,
  • Natalia M. Rougier,
  • Raquel V. Vico,
  • Susan A. Bourne,
  • Elba I. Buján,
  • Mino R. Caira and
  • Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

Graphical Abstract
  • shift was noted and the change in absorbance was not large enough for an accurate determination of the binding constant. The induced circular dichroism (ICD) spectrum of DIMEB and 1 is shown in Figure 9a, where the spectrum recorded for β-CD and TRIMEB with 1 is also shown for comparison. It can be seen
  • that the native β-CD and DIMEB show a negative and a positive peak (Figure 9a). The negative peaks appear at 320 and 324 nm and the positive ones at 260 and 265 nm for β-CD and DIMEB, respectively. The positive peak in the circular dichroism spectrum is slightly displaced from the maximum of the UV–vis
  • DIMEB·1 structure, viewed along [100] (left) and [010] (right). The symmetry related molecules are distinguished by the reverse green and black host and guest molecules. For clarity, only guest molecules A and B are shown and the hydrogen atoms have been omitted. Induced circular dichroism (a) and UV
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Published 17 Jan 2013

Multivalent display of the antimicrobial peptides BP100 and BP143

  • Imma Güell,
  • Rafael Ferre,
  • Kasper K. Sørensen,
  • Esther Badosa,
  • Iteng Ng-Choi,
  • Emilio Montesinos,
  • Eduard Bardají,
  • Lidia Feliu,
  • Knud J. Jensen and
  • Marta Planas

Beilstein J. Org. Chem. 2012, 8, 2106–2117, doi:10.3762/bjoc.8.237

Graphical Abstract
  • were significantly more active against both pathogens and were able to kill 99.99% of all cells within 30–90 min at 2.5 μM. Circular dichroism We investigated the secondary structures of carbopeptides 1 and 3 by analyzing their CD spectra at 100 μM in (i) 10 mM sodium phosphate buffer at pH 7.4; (ii
  • (Bruker Daltonics). High-resolution mass spectrometry (HRMS) was recorded on a Bruker MicroToF-Q MALDI instrument by using a hybrid quadrupole time-of-flight mass spectrometer (University of Zaragoza). Circular dichroism (CD) measurements were obtained using a Jasco spectropolarimeter (J-810, Easton, MD
  • , Madrid, Spain) as a positive control. The percentage of hemolysis (H) was calculated by using the following equation: H = 100 × [(Op−Ob)/(Om−Ob)], where Op was the density for a given compound concentration, Ob for the buffer, and Om for the melittin positive control. Circular dichroism spectroscopy
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Published 03 Dec 2012

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

  • Jan Hoyer,
  • Ulrich Schatzschneider,
  • Michaela Schulz-Siegmund and
  • Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

Graphical Abstract
  • -butyloxycarbonyl (Boc). Indeed, we did not observe concomitant deprotection of lysine side chains, which was favored by the fact that Mtt groups situated at the N-terminus are even more acid-sensitive than Nε-Mtt groups [25]. The structural analysis of the (sC18)2 conjugates by circular dichroism spectroscopy did
  • analytical RP-HPLC. For the peptide sequences see Table 1. Circular dichroism spectroscopy Circular dichroism spectra were recorded on a Jasco spectropolarimeter J 715 at 20 °C in 10 mM phosphate buffer (pH 7.0) with or without addition of 50% trifluoroethanol, respectively. The concentration of the peptides
  • triplicate with n = 2. Error bars represent the standard deviation. Chromatogram and ESI-MS of purified Cym2-GFL-(sC18)2. The gradient was 10→60% acetonitrile in water over 45 min. Circular dichroism spectra of the (sC18)2 conjugates. Spectra were acquired in 10 mM phosphate buffer with or without 50
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Published 18 Oct 2012

Antifreeze glycopeptide diastereomers

  • Lilly Nagel,
  • Carsten Budke,
  • Axel Dreyer,
  • Thomas Koop and
  • Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 1657–1667, doi:10.3762/bjoc.8.190

Graphical Abstract
  • replacement of L-threonine by its allo-L-diastereomer. Both glycopeptides were analyzed regarding their conformational properties, by circular dichroism (CD), and their ability to inhibit ice recrystallization in microphysical experiments. Keywords: bioorganic chemistry; circular dichroism; glycopeptides
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Published 01 Oct 2012

Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones

  • Sergei Žari,
  • Tiiu Kailas,
  • Marina Kudrjashova,
  • Mario Öeren,
  • Ivar Järving,
  • Toomas Tamm,
  • Margus Lopp and
  • Tõnis Kanger

Beilstein J. Org. Chem. 2012, 8, 1452–1457, doi:10.3762/bjoc.8.165

Graphical Abstract
  • configuration of the product 3a was determined by a comparison of the experimental and calculated vibrational circular dichroism (VCD) spectra. DFT calculations (method B3PW91/6-311G**) of a series of conformers of compound 3a with R-configuration were performed. Calculations of harmonic vibrational frequencies
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Published 04 Sep 2012

Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

  • Wenting Liang,
  • Cheng Yang,
  • Masaki Nishijima,
  • Gaku Fukuhara,
  • Tadashi Mori,
  • Andrea Mele,
  • Franca Castiglione,
  • Fabrizio Caldera,
  • Francesco Trotta and
  • Yoshihisa Inoue

Beilstein J. Org. Chem. 2012, 8, 1305–1311, doi:10.3762/bjoc.8.149

Graphical Abstract
  • substrates, including some pharmaceuticals [25], enzymes [26], pollutants [27], polymers [28], agrochemicals [29], and metal ions [30]. The complexation behavior of 1Z and 2ZZ with CDNSs was examined by means of circular dichroism spectroscopy, showing negative induced circular dichroism (ICD) at the 1La
  • the steric hindrance in the network polymer and/or the less efficient complexation inside the nanoparticle of CDNS would be responsible. The circular dichroism spectral changes observed for the more cross-linked CDNSs 4 and 5 upon binding 1Z or 2ZZ were too small to allow quantitative evaluation of
  • units with pH was examined by circular dichroism spectroscopy. As shown in Figure 2a, increasing the solution pH caused a significant enhancement of the negative ICD of CDNS 3. This seems reasonable, as the ionization of the carboxylic acid moieties on the PM units (pKa1 = 2.93 for pyromellitic acid
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Published 16 Aug 2012

Design of a novel tryptophan-rich membrane-active antimicrobial peptide from the membrane-proximal region of the HIV glycoprotein, gp41

  • Evan F. Haney,
  • Leonard T. Nguyen,
  • David J. Schibli and
  • Hans J. Vogel

Beilstein J. Org. Chem. 2012, 8, 1172–1184, doi:10.3762/bjoc.8.130

Graphical Abstract
  • observed antimicrobial effects. Circular dichroism spectroscopy The backbone conformations of all of the gp41 peptide derivatives were examined by using far-UV circular dichroism (CD) spectroscopy. The resulting CD spectra of the peptides in buffer, SDS, DPC and 50% trifluoroethanol (TFE) are shown in
  • previous scan, indicating that equilibrium had been reached. Circular dichroism spectroscopy CD spectra were collected at room temperature on a Jasco J815 spectropolarimeter by using a 0.1 cm path length cuvette. Far-UV spectra of 50 μM peptide solutions were collected between 190–260 nm with a 0.5 nm step
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Published 24 Jul 2012

Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity

  • Marta De Zotti,
  • Barbara Biondi,
  • Cristina Peggion,
  • Matteo De Poli,
  • Haleh Fathi,
  • Simona Oancea,
  • Claudio Toniolo and
  • Fernando Formaggio

Beilstein J. Org. Chem. 2012, 8, 1161–1171, doi:10.3762/bjoc.8.129

Graphical Abstract
  • activity. In each analogue, the single ψ[CS-NH] group was strategically incorporated either at an internal position of the amino-acid sequence, ψ[CS-NH]5, or near each of the two ends, ψ[CS-NH]2 and ψ[CS-NH]9. Moreover, the preferred conformations of these analogues were investigated by circular dichroism
  • Information File 1. Circular dichroism The CD spectra were measured on a Jasco (Tokyo, Japan) model J-715 spectropolarimeter equipped with a Haake thermostat (Thermo Fisher Scientific, Waltham, MA). Baselines were corrected by subtracting the solvent contribution. Fused quartz cells of 1.0 mm and 10.0 mm path
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Published 24 Jul 2012

Control over molecular motion using the cistrans photoisomerization of the azo group

  • Estíbaliz Merino and
  • María Ribagorda

Beilstein J. Org. Chem. 2012, 8, 1071–1090, doi:10.3762/bjoc.8.119

Graphical Abstract
  • conformational changes in polymers. There may also be variations in the organization of large assemblies of molecules in gels or liquid crystals. When polarized light is used, the photoisomerization often induces a reorganization of chromophores that can be reflected in the circular dichroism spectra. The basic
  • , 15 min) again enriches 46% of the trans isomer. The molecular motion was studied by circular dichroism (CD), 1H NMR and DFT calculations confirming that the change in the configuration of the N=N double bond modifies the initial position of the ferrocene resulting in an opening (cis) and closing
  • standard techniques (UV–vis, circular dichroism, chiral HPLC and NMR) has established that the chiral optical response differs greatly depending on the position of the sulfoxide group (C-2 or C-3). Cis isomers in both p-tolylsulfinyl azocompounds show an opposite arrangement of substituents around the N=N
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Published 12 Jul 2012

Investigation of the network of preferred interactions in an artificial coiled-coil association using the peptide array technique

  • Raheleh Rezaei Araghi,
  • Carsten C. Mahrenholz,
  • Rudolf Volkmer and
  • Beate Koksch

Beilstein J. Org. Chem. 2012, 8, 640–649, doi:10.3762/bjoc.8.71

Graphical Abstract
  • on a C-8 column (Phenomenex® Luna C8, 10 μM, 250 mm × 21.2 mm). The identities of peptides were confirmed using an ESI–TOF instrument. Circular-dichroism (CD) spectroscopy [18]: Peptide samples were analyzed in 10 mM phosphate buffer (pH 7.4). Far-ultraviolet circular-dichroism spectra and GndHCl
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Published 25 Apr 2012

Conserved and species-specific oxylipin pathways in the wound-activated chemical defense of the noninvasive red alga Gracilaria chilensis and the invasive Gracilaria vermiculophylla

  • Martin Rempt,
  • Florian Weinberger,
  • Katharina Grosser and
  • Georg Pohnert

Beilstein J. Org. Chem. 2012, 8, 283–289, doi:10.3762/bjoc.8.30

Graphical Abstract
  • , 5 and 6 were optically inactive and exhibited no signal in circular dichroism measurements. Both isomers 5 and 6 were already detected in the crude extracts, but also after work-up and during storage in CDCl3 further isomerization was observed. The biosynthetic origin of 5 and 6 from arachidonic
  • equipped with a Synergi MAX-RP 250 × 4.6 mm column (particle size 4 µm) from Phenomenex (Macclesfield, UK). Optical rotations were measured on a Jasco (Groß-Umstadt, Germany) 1030 polarimeter at 589 nm. Circular-dichroism spectra were recorded on a Jasco P810 instrument. Analytical thin-layer
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Published 21 Feb 2012

Fifty years of oxacalix[3]arenes: A review

  • Kevin Cottet,
  • Paula M. Marcos and
  • Peter J. Cragg

Beilstein J. Org. Chem. 2012, 8, 201–226, doi:10.3762/bjoc.8.22

Graphical Abstract
  • effect that occurred when the cations bound to the lower-rim esters, as indicated by increasingly complex 1H NMR patterns. When 46 bound to S-2-methylbutylammonium triflate, the presence of a chiral complex was confirmed by circular dichroism [53]. 4 Oxacalix[3]arene complexes 4.1 Complexation by parent
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Published 07 Feb 2012

Supramolecular FRET photocyclodimerization of anthracenecarboxylate with naphthalene-capped γ-cyclodextrin

  • Qian Wang,
  • Cheng Yang,
  • Gaku Fukuhara,
  • Tadashi Mori,
  • Yu Liu and
  • Yoshihisa Inoue

Beilstein J. Org. Chem. 2011, 7, 290–297, doi:10.3762/bjoc.7.38

Graphical Abstract
  • behavior of anthracenecarboxylate (AC) moieties. UV–vis, circular dichroism and fluorescence spectral studies revealed that two AC molecules are simultaneously included in the modified γ-CD cavity to form a right-handed screw and also that the naphthalene cap efficiently transfers the singlet energy to AC
  • carbonate. In contrast, capped γ-CD 6 showed a much higher solubility in water, as the naphthalene cap can hardly interact with another CD. The complexation behavior of AC with modified γ-CDs 6 and 7 was investigated by UV–vis, circular dichroism and fluorescence spectral studies. As shown in Figure 1, the
  • addition of 7 to an aqueous solution of AC (0.2 mM) caused an evident bathochromic shift of the 1La band of AC, which is probably due to the stacking complexation of two AC molecules in a single γ-CD cavity. Modified γ-CDs 6 and 7 showed moderate circular dichroism signals in the naphthalene-absorbing
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Published 07 Mar 2011
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