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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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The molecular recognition controlled stereomutation cycle in a dynamic helical assembly.

Mohit Kumar1, Madugula Drona Reddy, Ananya Mishra

  • 1Supramolecular Chemistry Laboratory, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bangalore, 560064, India. george@jncasr.ac.in.

Organic & Biomolecular Chemistry
|September 4, 2015
PubMed
Summary

A novel perylene bisimide molecule self-assembles into different helical structures—left-handed, right-handed, or racemic—depending on whether it binds with AMP, ATP, or inorganic phosphates. This allows for dynamic changes in molecular assembly based on specific phosphate binding.

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Area of Science:

  • Supramolecular chemistry
  • Organic materials science
  • Molecular self-assembly

Background:

  • Perylene bisimides (PBIs) are known for their unique photophysical properties and self-assembly behavior.
  • Designing functional molecules that respond to specific analytes is a key challenge in supramolecular chemistry.
  • Phosphate-binding units are crucial for developing sensors and responsive materials.

Purpose of the Study:

  • To develop a PBI-based system capable of dynamic helical assembly.
  • To investigate the influence of different phosphate-containing analytes (AMP, ATP, inorganic phosphate) on the self-assembly of a functionalized PBI.
  • To demonstrate a helix mutation cycle driven by competitive guest binding.

Main Methods:

  • Synthesis of a perylene bisimide derivative functionalized with a phosphate recognition moiety.
  • Spectroscopic and microscopic characterization of the self-assembled structures.
  • Binding studies with adenosine monophosphate (AMP), adenosine triphosphate (ATP), and inorganic phosphates.
  • Analysis of the helical assembly changes in response to different analytes.

Main Results:

  • The functionalized PBI self-assembled into distinct helical structures upon binding with AMP (left-handed), ATP (right-handed), and inorganic phosphates (racemic).
  • The system exhibited a reversible helix mutation cycle, demonstrating dynamic changes in supramolecular architecture.
  • Competitive binding experiments confirmed the selective response to different multivalent phosphate guests.

Conclusions:

  • A single PBI derivative can form tunable helical supramolecular architectures based on the specific phosphate analyte.
  • The developed system provides a platform for dynamic control over molecular assembly through guest recognition.
  • This work presents an unprecedented helix mutation cycle in dynamic supramolecular systems driven by competitive binding.