Formation of Two‐Dimensional Supramolecular Polymers by Amphiphilic Pyrene Oligomers

Vybornyi, Mykhailo; Rudnev, Alexander V.; Langenegger, Simon M.; Wandlowski, Thomas; Calzaferri, Gion; Häner, Robert

doi:10.1002/anie.201307029

Cited by 103 publications

(103 citation statements)

References 101 publications

(92 reference statements)

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“…Haner et al reported nanosheet formation with the pyrene unit. 35 Recently, we have discovered that the polymer, which was prepared from azide and alkyne-terminated tetra(ethylene glycol)-substituted phenyl-capped bithiophene derivatives by Cu-catalyzed Huisgen cycloaddition reaction, 36 could selfassemble into the nanosheet through polymer folding in an organic solvent. 37 We called our nanosheets "thiophene nanosheets" because they are 2D crystals of the thiophene units sandwiched by ethylene glycol layers.…”

Section: ■ Introductionmentioning

confidence: 99%

Effect of Polymerization on Hierarchical Self-Assembly into Nanosheets

Ikeda

2015

Langmuir

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The oligomers consisting of phenyl-capped bithiophene and tetra(ethylene glycol)s linked by azide-alkyne Huisgen cycloaddition were synthesized. The relationship between the degree of polymerization and self-assembling ability was investigated in o-dichlorobenzene and dimethyl sulfoxide. From the absorption spectrum, it was confirmed that the critical degree of polymerization (CDP) for thiophene unit aggregation was 4. The morphology of the aggregated product was observed by atomic force microscopy. The oligomers 4mer and 5mer could not self-assemble into well-defined structures due to the weak driving force for the self-assembly. In the cases of 6mer and 7mer, aggregates with nonwell-defined and nanosheet structures coexisted. In the cases of 8mer and 9mer, the nanosheet was the main product. The critical point between 7mer and 8mer could be confirmed by different aggregation behaviors in the cooling process of the solution (nonsigmoidal and sigmoidal). In the cases of 8mer and 9mer, polymer folding prior to intermolecular self-assembly, which was supported by sigmoidal aggregation behavior, leads to the nanosheet formation. On the contrary, shorter oligomers than 8mer experience intermolecular aggregation prior to intramolecular polymer folding, which was supported by the nonsigmoidal aggregation behavior. This is the first report to prove the existence of CDP for folded polymer nanosheet formation which requires hierarchical self-assembly, i.e., polymer folding followed by intermolecular self-assembly.

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Section: ■ Introductionmentioning

confidence: 99%

Effect of Polymerization on Hierarchical Self-Assembly into Nanosheets

Ikeda

2015

Langmuir

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“…1) are some of the most widely studied organic chromophores [49–52]. Moreover, we have reported on the aggregation and stacking properties of 1,8- and 1,6-dialkynylpyrene [53–54]. Fig.…”

Section: Introductionmentioning

confidence: 99%

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

Winiger¹,

Langenegger²,

Khorev³

et al. 2014

Beilstein J. Org. Chem.

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SummaryAromatic π–π stacking interactions are ubiquitous in nature, medicinal chemistry and materials sciences. They play a crucial role in the stacking of nucleobases, thus stabilising the DNA double helix. The following paper describes a series of chimeric DNA–polycyclic aromatic hydrocarbon (PAH) hybrids. The PAH building blocks are electron-rich pyrene and electron-poor perylenediimide (PDI), and were incorporated into complementary DNA strands. The hybrids contain different numbers of pyrene–PDI interactions that were found to directly influence duplex stability. As the pyrene–PDI ratio approaches 1:1, the stability of the duplexes increases with an average value of 7.5 °C per pyrene–PDI supramolecular interaction indicating the importance of electrostatic complementarity for aromatic π–π stacking interactions.

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“…Accordingly, as we synthesized that the bulk junction at 8 position exerts steric effect on the rotational motion of the phenyl ring, such effect was originated from the propeller-shaped TPA core and methyl acrylate groups with strong aggregation ability. [53,54] From emission spectrum (Fig. 1b).…”

Section: Design and Synthesis Of Target Moleculesmentioning

confidence: 99%

Triphenylamine-decorated BODIPY fluorescent probe for trace detection of picric acid

Zhang

Jin

et al. 2015

RSC Adv.

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Triphenylamine-Decorated BODIPY derivative TBMA was designed and synthesized. Luminogen aggregations were developed through taking advantages of twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) processes. In nonpolar solvents, the locally excited (LE) states of BODIPY luminogens emited intense yellow lights. Increasing solvent polarity brought the luminogens from LE to TICT state, causing a large bathochromic shift in the emission color and a dramatic decrease in emission efficiency. The red emission was greatly boosted by aggregate formation or AIE effect. We also discovered that TBMA could be applied as an efficient chemical sensor for PA detection. The detection limit and quenching constant (K SV ) were determined as 30 ppb and 2.1x10 -6 M -1 respectively. 19 F NMR and 1 H NMR titration analysis verified that F ... H hydrogen bonding is demonstrated as the interacting mode, which is of possibility to facilitates the effective exciton migration.

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Formation of Two‐Dimensional Supramolecular Polymers by Amphiphilic Pyrene Oligomers

Cited by 103 publications

References 101 publications

Effect of Polymerization on Hierarchical Self-Assembly into Nanosheets

Effect of Polymerization on Hierarchical Self-Assembly into Nanosheets

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

Triphenylamine-decorated BODIPY fluorescent probe for trace detection of picric acid

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