Oligoprolines guide the self-assembly of quaterthiophenes

Ochs, Nellie A. K.; Lewandowska, Urszula; Zaja̧czkowski, Wojciech M.; Corrà, Stefano; Reger, Stephan; Herdlitschka, Andreas; Schmid, Sylvia; Pisula, Wojciech; Müllen, Kläus; Bäuerle, Peter; Wennemers, Helma

doi:10.1039/c8sc05742g

Cited by 18 publications

(22 citation statements)

References 36 publications

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“…Oligoprolines did not self-assemble on their own but controlled the organization of quaterthiophene moiety. By varying the residue number in oligoproline, a substantial change in the molecular organization of the conjugates from monolayers to double-layered sheets and helically twisted ribbons was achieved [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

RETRACTED: Electroactive peptide-based supramolecular polymers

Garifullin

Güler

2021

Materials Today Bio

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The electroactivity as a supramolecular feature of intelligently designed self-assembled systems stimulates a wide interest in development of new stimuli-responsive biomaterials. A diverse set of nanostructures are fabricated through programmed self-assembly of molecules for functional materials. Electroactive groups are conjugated as a functional moiety for organic semiconductor applications. In this review, we present recent examples of self-assembling peptide molecules and electroactive units for supramolecular functional electronic and optical materials with potential biomedical and bioelectronics applications.

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Section: Introductionmentioning

confidence: 99%

RETRACTED: Electroactive peptide-based supramolecular polymers

Garifullin

Güler

2021

Materials Today Bio

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“…The presence of four azide-prolines in the sequence of polyproline allows modulating the functionalization of hydrophobic self-assembling moiety of macromolecules. Recently, the conjugation of a quaterthiophene moiety via a triazole linkage with oligoprolines allowed having biocompatible molecules with a variety of well-ordered, open chiral, self-assembled nanostructures [ 189 ]. The applications of oligothiophenes in the development of organic materials are important in the field of organic electronic devices [ 190 ].…”

Section: Peptides As “Tools” For (Bio)supramolecular Interactionmentioning

confidence: 99%

Peptide–Protein Interactions: From Drug Design to Supramolecular Biomaterials

2021

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The self-recognition and self-assembly of biomolecules are spontaneous processes that occur in Nature and allow the formation of ordered structures, at the nanoscale or even at the macroscale, under thermodynamic and kinetic equilibrium as a consequence of specific and local interactions. In particular, peptides and peptidomimetics play an elected role, as they may allow a rational approach to elucidate biological mechanisms to develop new drugs, biomaterials, catalysts, or semiconductors. The forces that rule self-recognition and self-assembly processes are weak interactions, such as hydrogen bonding, electrostatic attractions, and van der Waals forces, and they underlie the formation of the secondary structure (e.g., α-helix, β-sheet, polyproline II helix), which plays a key role in all biological processes. Here, we present recent and significant examples whereby design was successfully applied to attain the desired structural motifs toward function. These studies are important to understand the main interactions ruling the biological processes and the onset of many pathologies. The types of secondary structure adopted by peptides during self-assembly have a fundamental importance not only on the type of nano- or macro-structure formed but also on the properties of biomaterials, such as the types of interaction, encapsulation, non-covalent interaction, or covalent interaction, which are ultimately useful for applications in drug delivery.

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“… 37 This concept has been broadly applied using oligoproline conjugates for, e.g., tumor targeting, 38 light harvesting, 39 , 40 or in organic electronics. 41 Due to the low solubility in apolar organic solvents, most of the studies on oligoprolines have been performed in either water or polar organic solvents. 37 , 42 − 45 Yet, especially for the use of oligoprolines in supramolecular assemblies, where weak interactions such as van der Waals interactions or hydrogen bonding (H-bonding) are the main contributors, the use of noncompeting, apolar environments is highly desired.…”

Section: Introductionmentioning

confidence: 99%

Oligodimethylsiloxane-Oligoproline Block Co-Oligomers: the Interplay between Aggregation and Phase Segregation in Bulk and Solution

et al. 2021

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Discrete block co-oligomers (BCOs) assemble into highly ordered nanostructures, which adopt a variety of morphologies depending on their environment. Here, we present a series of discrete oligodimethylsiloxane-oligoproline ( o DMS- o Pro) BCOs with varying oligomer lengths and proline end-groups, and study the nanostructures formed in both bulk and solution. The conjugation of oligoprolines to apolar siloxanes permits a study of the aggregation behavior of oligoproline moieties in a variety of solvents, including a highly apolar solvent like methylcyclohexane. The apolar solvent is more reminiscent of the polarity of the siloxane bulk, which gives insights into the supramolecular interactions that govern both bulk and solution assembly processes of the oligoproline. This extensive structural characterization allows the bridging of the gap between solution and bulk assembly. The interplay between the aggregation of the oligoproline block and the phase segregation induced by the siloxane drives the assembly. This gives rise to disordered, micellar microstructures in apolar solution and crystallization-driven lamellar nanostructures in the bulk. While most di- and triblock co-oligomers adopt predictable morphological features, one of them, o DMS 15 - o Pro 6 -NH 2 , exhibits pathway complexity leading to gel formation. The pathway selection in the complex interplay between aggregation and phase segregation gives rise to interesting material properties.

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Oligoprolines guide the self-assembly of quaterthiophenes

Abstract: Oligoprolines of differing lengths control the self-assembly of quaterthiophenes into mono-layered or double-layered sheets, or helically twisted ribbons.

Cited by 18 publications

References 36 publications

RETRACTED: Electroactive peptide-based supramolecular polymers

RETRACTED: Electroactive peptide-based supramolecular polymers

Peptide–Protein Interactions: From Drug Design to Supramolecular Biomaterials

Oligodimethylsiloxane-Oligoproline Block Co-Oligomers: the Interplay between Aggregation and Phase Segregation in Bulk and Solution

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