Rethinking the term “pi-stacking”

Martinez, Chelsea R.; Iverson, Brent L.

doi:10.1039/c2sc20045g

Cited by 1,453 publications

(1,255 citation statements)

References 129 publications

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“…In the structure of the inclusion compound 3a with n-BuOH, the host molecules are chain-like connected along the a axis by π···π-interactions 27,28 Having the opportunity to isolate a suitable solvent free crystal of 4, we have been able to get an insight into the packing behavior of 4 without the influencing control of solvent interaction. In the structure, the two independent diol molecules ( Relating to the cage inclusions 4a and 4b (Fig.…”

Section: Resultsmentioning

confidence: 99%

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

Katzsch

Gruber

Weber

2015

Crystal Growth & Design

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By applying the 'wheel-and-axle' host concept and incorporating a previously developed heteroaromatic substitution strategy, a new type of diol hosts featuring two di(benzo [b]thien-2-yl)hydroxymethyl units attached to both ends of a central ethynylene (3) and 1,4-phenylene (4) moiety is reported. The syntheses of the host compounds are described and solvent inclusion formation via crystallization has extensively been studied showing a remarkable inclusion capability of the compounds. X-ray diffraction analysis of relevant crystal structures have been performed and comparatively discussed. Vapor sorption behavior of the compounds as solid receptor films coated on a quartz crystal microbalance considering a variety of solvent vapors has been scrutinized, indicating potential application as mass sensitive materials.3

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Section: Resultsmentioning

confidence: 99%

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

Katzsch

Gruber

Weber

2015

Crystal Growth & Design

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“…However, the nature of their electron density can play an important role in the self-assembly of NDI and PCSs and facilitate a donor-acceptor charge transfer interfaces. [ 58 ] NDIs in this family, including D-3 , D-4 , D-5 , and D-6 molecules contain strongly electron withdrawing groups in the periphery of the naphthalyn core and are suitable for face-centered stacking interactions with electron rich molecules. On the other hand, the π-electron density of molecules such as benzene or its larger congeners (graphene, TRGO, coronene) dominates the area above and below the plane of the hydrogens.…”

Section: Advmentioning

confidence: 99%

Thermally Reduced Graphene Oxide Nanohybrids of Chiral Functional Naphthalenediimides for Prostate Cancer Cells Bioimaging

Tyson

Mirabello

Calatayud

et al. 2016

Adv Funct Materials

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This study reports on the supramolecular assemblies formed between planar carbon systems (PCSs) such as thermally reduced graphene oxide (TRGO) and its small‐molecule model system coronene and a series of d‐ and l‐α amino acid derivatized naphthalenediimides (NDIs) where the halogen substituents (X = F, Cl, Br, I) are varied systematically. Confocal fluorescence microscopy of NDIs, NDI•coronene, and NDI•TRGO complexes is performed proving the uptake and stability of such complexes in the cellular environment and suggesting their potential as prostate cancer imaging agents. 1H NMR and UV–vis spectroscopy studies support the formation of charge transfer complexes whereby the increasing polarizability and general electronegativity of the aryl halide substituted at the NDI periphery influence the magnitude of the association constants in the ground state between NDI and coronene. Complexation between NDIs and PCSs also results in stable photoexcited assemblies within the solution (coronene) as well as the dispersed phased (TRGO). Fluorescence emission titrations and 2‐photon time correlated single photon counting measurements suggest the existence of dynamic quenching mechanisms upon the excitation of the fluorophore in the presence of the carbon substrates, as these methods are sensitive proves for the subtle changes in the NDI environment. The series of halogenated species used exerts supramolecular control over the degree of surface assembly on the TRGO and over the interactions with the coronene molecule, and this is of relevance to the assembly of future biosensing platforms as these materials can both be viewed as congeners of graphene. Finally, MTT assays carried out in PC‐3 cells demonstrate that the stable noncovalent functionalization of TRGO and coronene with either l or d NDIs remarkably improves the cellular viability in the presence of such graphene‐like materials. These phenomena are of particular relevance for the understanding of the direct donor–acceptor interactions in solutions which govern the design of nanomaterials with future biosensing and bioimaging applications.

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“…The second is a preferred orientation of the alkyl chains with the surface lattice because the carbon position in the alkyl chains is closely matched with the graphene surfaces [105,108,116,117,138,139]. The π-π interactions infer face-to-face stacking (see Fig.5A) of the surfactant containing aromatic ring(s) and the graphene basal planes involved in the non-covalent interactions [151], although the nature of this remains controversial [152,153]. It is not really well understood why the basal plane of graphene is more interacting than the graphene edges, and evidence is limited on modelling and scanning tunneling microscopy (STM) studies [146,148,[154][155][156].…”

Section: Accepted M Manuscriptmentioning

confidence: 99%

Graphene-philic surfactants for nanocomposites in latex technology

Mohamed

Ardyani

Bakar

et al. 2016

Advances in Colloid and Interface Science

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Graphene is the newest member of the carbon family, and has revolutionized materials science especially in the field of polymer nanocomposites. However, agglomeration and uniform dispersion remains an Achilles" heel (even an elephant in the room), hampering the optimization of this material for practical applications. Chemical functionalization of graphene can overcome these hurdles but is often rather disruptive to the extended piconjugation, altering the desired physical and electronic properties. Employing surfactants as stabilizing agents in latex technology circumvents the need for chemical modification allowing for the formation of nanocomposites with retained graphene properties. This article reviews the recent progress in the use of surfactants and polymers to prepare graphene/polymer nanocomposites via latex technology. Of special interest here are surfactant structure-performance relationships, as well as background on the roles surfactantgraphene interactions for promoting stabilization.

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Rethinking the term “pi-stacking”

Cited by 1,453 publications

References 129 publications

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

Thermally Reduced Graphene Oxide Nanohybrids of Chiral Functional Naphthalenediimides for Prostate Cancer Cells Bioimaging

Graphene-philic surfactants for nanocomposites in latex technology

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