Structure and luminescence properties of supramolecular polymers of amphiphilic aromatic thioether–peptide conjugates in water

Ahlers, Patrick; Götz, Christian; Riebe, Steffen; Zirbes, Michael; Jochem, Matthias; Spitzer, D.; Voskuhl, Jens; Basché, Thomas; Besenius, Pol

doi:10.1039/c8py01712c

Cited by 10 publications

(12 citation statements)

References 44 publications

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“… 206 In a series of phthalonitriles functionalized with linear peptides, the balance between hydrogen bonding and hydrophobicity directed the flexibility but not length of the supramolecular polymers. 207 …”

Section: Solvent Effects On Supramolecular Polymers In Aqueous Systemmentioning

confidence: 99%

“…In sugar-decorated, water-soluble BTA derivatives, hydrogen bonding of water was found to increase the dynamic behavior of the supramolecular polymers . In a series of phthalonitriles functionalized with linear peptides, the balance between hydrogen bonding and hydrophobicity directed the flexibility but not length of the supramolecular polymers …”

Section: Solvent Effects On Supramolecular Polymers In Aqueous Systemsmentioning

confidence: 99%

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Solute–Solvent Interactions in Modern Physical Organic Chemistry: Supramolecular Polymers as a Muse

2020

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Interactions between solvents and solutes are a cornerstone of physical organic chemistry and have been the subject of investigations over the last century. In recent years, a renewed interest in fundamental aspects of solute–solvent interactions has been sparked in the field of supramolecular chemistry in general and that of supramolecular polymers in particular. Although solvent effects in supramolecular chemistry have been recognized for a long time, the unique opportunities that supramolecular polymers offer to gain insight into solute–solvent interactions have become clear relatively recently. The multiple interactions that hold the supramolecular polymeric structure together are similar in strength to those between solute and solvent. The cooperativity found in ordered supramolecular polymers leads to the possibility of amplifying these solute–solvent effects and will shed light on extremely subtle solvation phenomena. As a result, many exciting effects of solute–solvent interactions in modern physical organic chemistry can be studied using supramolecular polymers. Our aim is to put the recent progress into a historical context and provide avenues toward a more comprehensive understanding of solvents in multicomponent supramolecular systems.

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Section: Solvent Effects On Supramolecular Polymers In Aqueous Systemmentioning

confidence: 99%

Section: Solvent Effects On Supramolecular Polymers In Aqueous Systemsmentioning

confidence: 99%

Solute–Solvent Interactions in Modern Physical Organic Chemistry: Supramolecular Polymers as a Muse

2020

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“…Overall five AIE modified GCP functionalized oligomers (O1-O5) were synthesized. The AIE luminophore, based on aromatic thioethers described by Voskuhl et al, [27,28] varies in its position from the direct vicinity of the binding motif to the middle of the side chain or main chain to the position as end group of the oligomer (Scheme 1). All oligomers were synthesized using previously established solid phase polymer synthesis protocols, combining tailor-made building blocks such as EDS (4-((2-(2-(2aminoethoxy)ethoxy)ethyl)-amino)-4-oxobutanoic), [25] commercially available amino acids such as N α -Fmoc-N β -Boc-L-2,3diaminopropionic acid (DAP), carboxy-functionalized GCP building block and carboxylated aromatic thioether (CATE) as AIE.…”

Section: Resultsmentioning

confidence: 99%

Take your Positions and Shine: Effects of Positioning Aggregation‐Induced Emission Luminophores within Sequence‐Defined Macromolecules

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Killa

Junghans

et al. 2021

Chemistry A European J

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A luminophore with aggregation‐induced emission (AIE) is employed for the conjugation onto supramolecular ligands to allow for detection of ligand binding. Supramolecular ligands are based on the combination of sequence‐defined oligo(amidoamine) scaffolds and guanidiniocarbonyl‐pyrrole (GCP) as binding motif. We hypothesize that AIE properties are strongly affected by positioning of the luminophore within the ligand scaffold. Therefore, we systematically investigate the effects placing the AIE luminophore at different positions within the overall construct, for example, in the main or side chain of the olig(amidoamine). Indeed, we can show that the position within the ligand structure strongly affects AIE, both for the ligand itself as well as when applying the ligand for the detection of different biological and synthetic polyanions.

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“…In the limit of small effective hydrophobicity, monomers can also be modeled with a rigid structure. Further, though the study involves a specific symmetry, these principles of successful assembly can be utilized to synthesize monomers with different symmetries 45 via tuning the range of attraction and excluded volume (Supporting Information and Supplemental Figure 12). Thus, the model, apart from its computational efficiency, goes beyond the specific monomer considered here and provides an elemental recipe for fabrication of stable, one-dimensional nanostructures.…”

Section: ■ Conclusionmentioning

confidence: 99%

Modeling Supramolecular Polymerization: The Role of Steric Effects and Hydrophobic Interactions

et al. 2019

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We present a combined experimental–simulation study of self-assembly into one-dimensional filaments. Experimentally, we study amphiphilic AuI-metallopeptides in neutral aqueous media. Our model focuses on two aspects of the monomers, their geometry and their hydrophobic core. We demonstrate numerically that a coarse-grained, generic model is sufficient to obtain spontaneous formation of nearly defect-free, long supramolecular polymers at experimentally relevant monomer concentrations. In the simulations, we find both nonchiral and helical polymer morphologies depending on the effective hydrophobic strength. We analyze the assembly kinetics, comparing simulations to experimental data obtained from circular dichroism spectroscopy, and relate both to kinetic models of nucleated polymerization. While the simulations proceed via nucleation and elongation, experimental kinetics seems to involve fragmentation.

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Structure and luminescence properties of supramolecular polymers of amphiphilic aromatic thioether–peptide conjugates in water

Abstract: We present the preparation of luminophore–peptide conjugates that self-assemble into phosphorescent supramolecular polymers in neutral buffer.

Cited by 10 publications

References 44 publications

Solute–Solvent Interactions in Modern Physical Organic Chemistry: Supramolecular Polymers as a Muse

Solute–Solvent Interactions in Modern Physical Organic Chemistry: Supramolecular Polymers as a Muse

Take your Positions and Shine: Effects of Positioning Aggregation‐Induced Emission Luminophores within Sequence‐Defined Macromolecules

Modeling Supramolecular Polymerization: The Role of Steric Effects and Hydrophobic Interactions

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