Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Synthesis of helical ladder polymers

21.05.2019

Ladder polymers -- molecules made of adjacent rings sharing two or more atoms -- are challenging to synthesize, because they require highly selective, quantitative reactions to avoid the formation of branching structures or of interruptions in the ring sequence in the polymer chain.

Moreover, most existing strategies for the synthesis of ladder polymers suffer from severe limitations in terms of selectivity and quantitativity. Another important type of molecules are molecules with a helical structure (such as DNA and proteins), which play an important role in molecular recognition and catalysis.


A construction of macro-scale architectures with a helical ladder shape is not even a challenge, but it's a different story when it comes to a molecular scale. Here, the efficient synthesis of one-handed helical ladder polymers is established through a trifluoroacetic acid (TFA)-assisted intramolecular cyclization of chiral triptycenes.

Credit: Kanazawa University

Usage Restrictions: The image may only be used with appropriate caption and credit.

Thus, the fabrication of molecules that possess both a ladder and a helical structure could open up new applications of polymeric materials.

Tomoyuki Ikai, Timothy M. Swager and colleagues from an international collaboration started from triptycene, an aromatic hydrocarbon that is an achiral molecule, but from which chiral derivatives can be obtained by introducing substituents in the benzene rings in an asymmetric manner.

Optically active triptycenes have practical uses as chiral materials, for example for chiral separation and circularly polarized luminescent materials.

The researchers then used the chiral triptycenes as a framework to efficiently form single-handed helical ladder polymers using electrophilic aromatic substitution. Steric repulsion in the system resulted in the formation of one-handed twisted ladder units.

The reactions were quantitative and regioselective (that is, there is a preferred direction of chemical bonding), which enabled the synthesis of optically active ladder polymers with well-defined helical geometry. No byproducts were detected.

Several techniques, including spectroscopy and microscopy techniques, were used to characterize the reaction products during synthesis, and molecular dynamics simulations were employed to understand the structure of the resulting molecules, confirming the right-handed helical ladder geometry. The researchers also measured the optical activity of the molecules.

The newly reported synthesis route will open up the synthesis of nanoscale helical ladder architectures and optically active chiral materials. "We believe that these ladder polymers, which can fall into a new category of helical polymers, represent a promising class of advanced materials for use as nanochannels for molecular/ion transport, organic electronics, specific reaction fields, and functional hosts through further modification of the backbone and pendant units," commented the authors in the paper.

Tomoya Sato | EurekAlert!
Further information:
https://pubs.acs.org/doi/10.1021/jacs.8b13865
http://dx.doi.org/10.1021/jacs.8b13865

More articles from Materials Sciences:

nachricht Machine learning methods provide new insights into organic-inorganic interfaces
04.08.2020 | Technische Universität Graz

nachricht Unusual electron sharing found in cool crystal
31.07.2020 | Nagoya University

All articles from Materials Sciences >>>

The most recent press releases about innovation >>>

Die letzten 5 Focus-News des innovations-reports im Überblick:

Im Focus: AI & single-cell genomics

New software predicts cell fate

Traditional single-cell sequencing methods help to reveal insights about cellular differences and functions - but they do this with static snapshots only...

Im Focus: TU Graz Researchers synthesize nanoparticles tailored for special applications

“Core-shell” clusters pave the way for new efficient nanomaterials that make catalysts, magnetic and laser sensors or measuring devices for detecting electromagnetic radiation more efficient.

Whether in innovative high-tech materials, more powerful computer chips, pharmaceuticals or in the field of renewable energies, nanoparticles – smallest...

Im Focus: Tailored light inspired by nature

An international research team with Prof. Cornelia Denz from the Institute of Applied Physics at the University of Münster develop for the first time light fields using caustics that do not change during propagation. With the new method, the physicists cleverly exploit light structures that can be seen in rainbows or when light is transmitted through drinking glasses.

Modern applications as high resolution microsopy or micro- or nanoscale material processing require customized laser beams that do not change during...

Im Focus: NYUAD astrophysicist investigates the possibility of life below the surface of Mars

  • A rover expected to explore below the surface of Mars in 2022 has the potential to provide more insights
  • The findings published in Scientific Reports, Springer Nature suggests the presence of traces of water on Mars, raising the question of the possibility of a life-supporting environment

Although no life has been detected on the Martian surface, a new study from astrophysicist and research scientist at the Center for Space Science at NYU Abu...

Im Focus: Manipulating non-magnetic atoms in a chromium halide enables tuning of magnetic properties

New approach creates synthetic layered magnets with unprecedented level of control over their magnetic properties

The magnetic properties of a chromium halide can be tuned by manipulating the non-magnetic atoms in the material, a team, led by Boston College researchers,...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

VideoLinks
Industry & Economy
Event News

“Conference on Laser Polishing – LaP 2020”: The final touches for surfaces

23.07.2020 | Event News

Conference radar for cybersecurity

21.07.2020 | Event News

Contact Tracing Apps against COVID-19: German National Academy Leopoldina hosts international virtual panel discussion

07.07.2020 | Event News

 
Latest News

First radio detection of an extrasolar planetary system around a main-sequence star

04.08.2020 | Physics and Astronomy

The art of making tiny holes

04.08.2020 | Physics and Astronomy

Early Mars was covered in ice sheets, not flowing rivers

04.08.2020 | Physics and Astronomy

VideoLinks
Science & Research
Overview of more VideoLinks >>>