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Search for "π-stacking" in Full Text gives 207 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

  • Sushil K. Maurya and
  • Rohit Rana

Beilstein J. Org. Chem. 2017, 13, 1106–1118, doi:10.3762/bjoc.13.110

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  • inherent properties including stability towards acid–base hydrolysis, active participation in H-bonding, dipole–dipole and π-stacking interactions [37][64][65][66]. The reaction would then afford a range of acyclic precursors, which could then undergo the intramolecular cyclization reaction to furnish the
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Published 09 Jun 2017

Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

  • Frederik Neuhaus,
  • Fabio Zobi,
  • Gerald Brezesinski,
  • Marta Dal Molin,
  • Stefan Matile and
  • Andreas Zumbuehl

Beilstein J. Org. Chem. 2017, 13, 1099–1105, doi:10.3762/bjoc.13.109

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  • change is significant and represents the expected red shift. Although contributions from changes in π–π stacking on spectroscopic properties cannot be excluded, the observed red shift in compressed flipper monolayers is consistent with the earlier experiments on the planarization of monomeric flipper
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Published 08 Jun 2017

Substitution of fluorine in M[C6F5BF3] with organolithium compounds: distinctions between O- and N-nucleophiles

  • Anton Yu. Shabalin,
  • Nicolay Yu. Adonin and
  • Vadim V. Bardin

Beilstein J. Org. Chem. 2017, 13, 703–713, doi:10.3762/bjoc.13.69

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  • (Scheme 9) due to the π-stacking interactions between C6H5 and C6F5 moieties (Scheme 10), which is excluded in cases of nucleophilic alkylation. While reactions of K[C6F5BF3] with C-nucleophiles give the significant amount of K[2-NuC6F4BF3] the related isomers are not formed under the action of O
  • ). During nucleophilic phenylation the πstacking interaction between C6H5 and C6F5 moieties can be responsible for increased yield of M[2-PhC6F4BF3]. 4. The formation of M[2-RC6F4BF3] proceeds through the coordination of RLi (polarized C–Li bond) to a fluorine atom of the BF3 moiety and subsequent
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Published 12 Apr 2017

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

  • Stephen Hill and
  • M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

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  • interaction between the positively charged amino group in DOX and the negatively charged groups on the CD surface can take place. Also van der Waals and π–π stacking interactions were attributed as contributing factors to the DOX loading and DOX incorporation into the hollow CD cavity. Drug release at acidic
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Published 10 Apr 2017

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

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  • ][21][22]. As mentioned above, developing a new gelator is still largely a trial and error method. The most widely used design strategy involves the inclusion of structural components favouring intermolecular non-covalent interactions (like H-bonding, π-stacking, donor–acceptor interaction, metal
  • ][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
  • geometry (unlike the planar geometry of say anthracene, pyrene, etc.), π–π stacking will be favoured only between benzene units of different trityl groups. A small library of triphenylmethyl derivatives was synthesized from the corresponding primary alcohols employing a single step reaction and detailed
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Published 23 Jan 2017

Supramolecular frameworks based on [60]fullerene hexakisadducts

  • Andreas Kraft,
  • Johannes Stangl,
  • Ana-Maria Krause,
  • Klaus Müller-Buschbaum and
  • Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

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  • ][34][35][36][37][38][39][40][41][42][43][44][45] or π–π-stacking [46] that retain porosity in the solid state under activation conditions have been reported so far. One possible way to enhance stability and shape-persistency might be the implementation of polyfunctional building blocks in order to
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Published 02 Jan 2017

Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction

  • Salvatore V. Giofrè,
  • Santa Cirmi,
  • Raffaella Mancuso,
  • Francesco Nicolò,
  • Giuseppe Lanza,
  • Laura Legnani,
  • Agata Campisi,
  • Maria A. Chiacchio,
  • Michele Navarra,
  • Bartolo Gabriele and
  • Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

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  • 180° rotation of the isoindolinone core such that the benzyl group and dialkylamide occupy the Leu26 and Phe19 pockets, respectively. The reoriented binding mode, similar to the MI63 analogue, takes advantage of the π–π stacking interaction with His96 of MDM2 and the benzyl moiety of compound 6e, and
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Published 20 Dec 2016

Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

  • John A. Love,
  • Shu-Hua Chou,
  • Ye Huang,
  • Guilllermo C. Bazan and
  • Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

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  • reflection, suggesting a quite well-ordered film. Additionally, there is a small peak at 1.79 Å−1, corresponding to a spacing of 3.5 Å, which we attribute to π–π stacking. There is a broad feature centered at Q = 1.5 Å−1 which is seen in both films and at all orientations, which is the convolution of two
  • with DIO, the alkyl stacking peak is again though is less prominent in-plane, while the π-stacking peak is more prominent. Assuming the alkyl and π-stacking directions are perpendicular, this suggests the material primarily adopts an edge-on orientation. This is in contrast with the preferential “face
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Published 28 Nov 2016

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

  • Ulrike Kauscher and
  • Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

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  • inclusion between the adamantane groups and the cyclodextrin cavities at the surface of cyclodextrin vesicles (CDVs) results in efficient immobilization of the squaraine on a nanocarrier. In addition, π–π stacking (and hence inactivation) of the squaraine is supressed due to the steric separation of the
  • . In a first set of experiments, we investigated the photochemical properties of AdSq in acetonitrile (Figure 2). The absorption spectrum shows a peak at 665 nm indicative of the presence of squaraine monomers in the solution. A shoulder around 610 nm indicates aggregation of the squaraine due to π–π
  • stacking. A comparison of absorption spectra in different solvents revealed that the amount of aggregation is rather low in acetonitrile or ethanol but increases dramatically if water is used as a solvent (see Figure S1 in Supporting Information File 1). This is in agreement with literature and highlights
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Published 25 Nov 2016

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

  • Florin Albota,
  • Mino R. Caira,
  • Constantin Draghici,
  • Florea Dumitrascu and
  • Denisa E. Dumitrescu

Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245

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  • of 12c include two additional intermolecular C–H···O bonds and an offset π-stacking interaction between the indolizine ring and its inversion-related counterpart, with the shortest centroid···centroid distance 3.718(1) Å. The 1H NMR spectra of compounds 12 confirmed the indolizine structure of the
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Published 23 Nov 2016

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

  • Paul B. Geraghty,
  • Calvin Lee,
  • Jegadesan Subbiah,
  • Wallace W. H. Wong,
  • James L. Banal,
  • Mohammed A. Jameel,
  • Trevor A. Smith and
  • David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

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  • evident (Figure 5a). However, λmax is dependent on the degree of formation of π–π stacking and development of the lowest energy transition with two clear sharp peaks at 552 nm and 590 nm (λmax) for BMR, while for BPR λmax is at 594 nm with a shoulder at around 630 nm indicating poor formation of the
  • cm−2. BPR shows promise with a high FF (74%), however a lower Voc (0.82 V) and a reduced Jsc (14.3 mA cm−2) reduce the PCE to 8.7%. UV–vis data indicate that under these SVA conditions the π–π stacking is not fully developed indicating that optimizing SVA conditions may lead to improved light
  • architecture described above. The collected device data are summarized in Table 5, and the J–V curves are shown in Figure 13. Examination of the BTxR UV–vis data for as-cast films (Figure 5d) indicates that BT8R does not have a well-developed π–π stacking peak in as-cast films, unlike BTR. Also, both BT4R and
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Published 02 Nov 2016

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

Graphical Abstract
  • structure is distorted tetrahedral with favorable π–π stacking distances between the proximal phenyl and pyrrole rings of the two separate ligands (Figure 10a and 10b). The distance between centroids is 3.56 Å for Zn(L2)2, compared to 3.63 Å for Zn(ADP)2 [38]. The shorter distance found for Zn(L2)2 suggests
  • a stronger interaction between the proximal phenyl and pyrrole rings than in Zn(ADP)2. Unfortunately, it cannot be determined whether the addition of fluorine or phenylacetylene contributed to the shorter π–π stacking distances without a crystal structure for Zn(WS3)2. Intermolecular favorable π–π
  • distorted tetrahedral shape; b) Shows the π-stacking between the proximal phenyl group of one ligand and a pyrrole ring of the opposite ligand. Generic synthetic scheme for fluorinated free ligands, where L# corresponds to the desired ligand number. For instance, L3-ADP and L3-ADPI2 would lead to the
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Published 29 Aug 2016

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

  • Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

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  • -helices; aromatic interactions; β-hairpin peptides; cation–π interactions; dynamic combinatorial chemistry; histone; molecular recognition in water; nucleosome; π–π-stacking; post-translational modification; supramolecular chemistry; Review Childhood influences When thinking about how to start writing
  • postdoc. Seminal work probing the electrostatic component of π–π stacking and edge-face aromatic interactions as well as cation–π interactions was being published at the time, as well as tantalizing suggestions about their relevance in biological structure and function. In particular, I was inspired by
  • -Sanders Model for π–π stacking from 1990 [4]. (d) Kool’s nonpolar isostere of thymidine from 1995 [5].(e) Gellman’s model for π–π stacking in aqueous solution [6]. (a) Model β-hairpin for investigation of aromatic interactions. (b) Examples of noncovalent interactions studied, from weakest to strongest
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Published 17 Aug 2016

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

  • Adrian E. Ion,
  • Liliana Cristian,
  • Mariana Voicescu,
  • Masroor Bangesh,
  • Augustin M. Madalan,
  • Daniela Bala,
  • Constantin Mihailciuc and
  • Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

Graphical Abstract
  • supramolecular interactions are observed in the crystal packing, via the azulene moieties and the terpyridine groups. In the crystal of 4a, the molecules are organized in columns running along the crystallographic a axis by π–π stacking interactions (3.39–3.64 Å). In the neighboring columns the molecular units
  • structures, different twisting was observed that might be responsible for the observed fluorescent profile. The solid-state crystal packing showed π–π stacking interactions between the pyridine rings in face-to-face or T-shape orientation, completed by slipped-off π–π stacked azulenyl moieties according to
  • ; found: C, 83.4; H, 5.2; N, 10.8; MS (ESI+, m/z): 402 (100, MH+), 403 (30%). Molecular structure and numbering scheme of 4′-(1-azulenyl)-2,2′:6′,2″-terpyridine (4a, left) and 4′-(1-(4,6,8-trimethyl-azulenyl)-2,2′:6′,2″-terpyridine (4b, right). Packing diagram for 4a showing the π–π stacking and CH–π
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Published 11 Aug 2016

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

  • Ni Yin,
  • Lilei Wang,
  • Yi Lin,
  • Jinduo Yi,
  • Lingpeng Yan,
  • Junyan Dou,
  • Hai-Bo Yang,
  • Xin Zhao and
  • Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

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  • oligothiophene chains. In the solid state, absorption spectra of these compounds (see Figure 1b) are remarkably broadened and red-shifted relative to those in solutions, which is attributable to strong π–π stacking interaction between the molecular backbones in the solid films [31][32]. It is noticeable that
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Published 10 Aug 2016

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

  • Desta Gedefaw,
  • Marta Tessarolo,
  • Margherita Bolognesi,
  • Mario Prosa,
  • Renee Kroon,
  • Wenliu Zhuang,
  • Patrik Henriksson,
  • Kim Bini,
  • Ergang Wang,
  • Michele Muccini,
  • Mirko Seri and
  • Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

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  • interchain π–π stacking, BDT is a widely used electron-rich monomer. Moreover, alkyl or aryl groups can easily be introduced to BDT basic units as side groups to finely tune the properties of the resulting polymers, not only in terms of solubility but also contributing, for example, to extend the π
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Published 01 Aug 2016

Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction

  • Valeria Corne,
  • Ariel M. Sarotti,
  • Carmen Ramirez de Arellano,
  • Rolando A. Spanevello and
  • Alejandra G. Suárez

Beilstein J. Org. Chem. 2016, 12, 1616–1623, doi:10.3762/bjoc.12.158

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  • , Universidad de Valencia, Valencia 46100, Spain 10.3762/bjoc.12.158 Abstract Chiral acrylic esters derived from biomass were developed as models to have a better insight in the aryl–vinyl π-stacking interactions. Quantum chemical calculations, NMR studies and experimental evidences demonstrated the presence
  • affected by the electron density of the aromatic counterpart. Keywords: acrylic esters; asymmetric synthesis; biomass; conformational equilibrium; π-stacking interaction; Introduction Noncovalent interactions have demonstrated to have relevant importance in chemistry and biology [1][2][3][4]. Considering
  • all noncovalent interactions, π-stacking is perhaps the less well understood, although its application in materials sciences, enzyme design and template-directed synthesis have had a dramatic growth, mainly for arene–arene interactions [1][2][3][4][5][6][7][8]. In particular, the use of π–π overlap as
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Published 28 Jul 2016

Creating molecular macrocycles for anion recognition

  • Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

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  • triazole nitrogens but not past the pyridine with the steric protection provided by a CH group (see the red arrows in Figure 4c for the overlay of the two ligands). The ruthenium complex showed intermolecular π stacking of ligands on neighboring complexes in the solid state; yet terpyridine analogs did not
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Published 31 Mar 2016

My maize and blue brick road to physical organic chemistry in materials

  • Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

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  • grateful for his time and advice. While on the academic interview circuit, I was fortunate to have Steven Wheeler (a postdoctoral researcher with Professor Ken Houk at the time) in the audience at one interview. He was developing computational methods to evaluate π-stacking interactions, and was intrigued
  • explained by through-space interactions [15]. Steven, who is now an associate professor at Texas A&M University, is changing the way we understand π stacking, XH/π, and ion/π interactions in organic systems [16][17][18][19][20]. During my postdoctoral studies, I remained fascinated with gels and was
  • structures, such as ribbons, fibers, and sheets. This self-aggregation is driven by noncovalent interactions, including hydrogen bonding, π stacking, van der Waals interactions, and halogen bonding. Physical interactions amongst these larger structures lead to gel formation. Because noncovalent interactions
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Published 08 Feb 2016

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

  • Xiang Sun,
  • Guoqiao Lai,
  • Zhifang Li,
  • Yuwen Ma,
  • Xiao Yuan,
  • Yongjia Shen and
  • Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

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  • driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and π–π stacking interactions. The electronic conductivity of the T1 and T2 films was tested by a four-probe method. Keywords: hydrogen bond; nanoribbon; self-assembly; tetrathiafulvalene; urethane; Introduction
  • nanomaterials is generally accepted to be the self-assembly of supermolecules, which is constructed through weak noncovalent interactions such as π–π stacking, van der Waals interactions, charge transfer and H-bonding interactions [3][4][5][6]. Generally speaking, H-bonding interactions are the key
  • units and urethane groups (Figure 1). The combination of the urethane group (forming hydrogen bonds) and the TTF unit (forming π–π stacking) may promote the formation of nanostructures. To the best of our knowledge, urethane groups have been rarely introduced into the molecular structure of TTF
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Published 27 Nov 2015

Supramolecular chemistry: from aromatic foldamers to solution-phase supramolecular organic frameworks

  • Zhan-Ting Li

Beilstein J. Org. Chem. 2015, 11, 2057–2071, doi:10.3762/bjoc.11.222

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  • : applications for molecular recognition and self-assembly Donor–acceptor interaction and π-stacking for folding. In January 2001, I returned to SIOC again. When I left SIOC for Urbana in 2000, I had built a small research group with two graduates. Thanks to the persistence of Professor Xi-Kui Jiang [19][20
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Published 02 Nov 2015

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

  • Alexander L. Kanibolotsky,
  • Neil J. Findlay and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

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  • dimensionality of charge carrier transport [1] by involving π–π stacking interactions. Varying the substituents of the conjugated backbone allows control over the polymer’s effective conjugation length and electronic properties, whilst also influencing the extent of inter-chain interactions. Two of the most
  • the preparation of TTF mixed valance state materials, which showed superconducting properties [25]. Fusing the TTF unit with dithiin rings in bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) led to the extension of 1D π–π stacking intermolecular interactions in a donor sheet of a mixed valance state
  • -acceptor into the conjugated backbone led to a polymer with a narrow optical band gap (Egopt = 1.32 eV in CH2Cl2 solution), with the expected lower value of Egopt = 1.26 eV in the film due to π–π stacking interactions. The value of the HOMO/LUMO levels (−5.13/−3.49 eV) in the film were noticeably different
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Published 28 Sep 2015

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

  • Masahiko Iyoda and
  • Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

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  • interactions between molecules having one or more unpaired electrons [3][4], neutral TTF and its derivatives also easily form stacked columnar structures with face-to-face π···π stacking and side-by-side S···S interactions in the crystalline state. Furthermore, weak intermolecular interactions (hydrogen
  • bonding, metal coordination, CT interaction, π···π stacking, van der Waals interaction, etc.) play an important role in the formation of the three-dimensional (3D) crystal structures [5]. For the construction of nanostructured objects, π···π, S···S, and other weak intermolecular interactions first
  • formed by casting a solution of 48 on a glass surface (Figure 17c). XRD studies on the fiber and the film of 48 revealed that the fiber has a hexagonal alignment, whereas the film has a lamellar structure with lateral order and π···π stacking. It is worth noting that the film of 48 prepared by casting a
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Published 10 Sep 2015

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

  • Rupert G. D. Taylor,
  • Joseph Cameron,
  • Iain A. Wright,
  • Neil Thomson,
  • Olena Avramchenko,
  • Alexander L. Kanibolotsky,
  • Anto R. Inigo,
  • Tell Tuttle and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

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  • resolved but there is a non-resolved peak caused by overlap of the cathodic peaks on the reverse scan. Compound 2 appears to show a first oxidation wave at 0.09 V, however, this is an artefact due to a minor degree of aggregation induced by π–π stacking between some of the molecules. This is followed by
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Published 10 Jul 2015

Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

  • Tobias-Elias Gloe,
  • Insa Stamer,
  • Cornelia Hojnik,
  • Tanja M. Wrodnigg and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 1096–1104, doi:10.3762/bjoc.11.123

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  • ]. Obviously, FimH binds α-D-mannosides such as simple methyl α-D-mannoside (MeMan, 1) but not β-mannosides. Mannosides with an aromatic aglycone, such as p-nitrophenyl α-D-mannoside (pNPMan) and 4-methylumbelliferyl α-D-mannoside (3) show an improved affinity to FimH due to π–π-stacking interactions of the
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Published 30 Jun 2015
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