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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
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Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
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Deducing the conformational space for an octa-proline helix.

Sara M A Waly1, Andrew C Benniston1, Anthony Harriman1

  • 1Molecular Photonics Laboratory, Bedson Building, School of Natural and Environmental Sciences, Newcastle University Newcastle upon Tyne NE1 7RU UK anthony.harriman@ncl.ac.uk.

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|February 2, 2024
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This study synthesized a PY-P8-PER molecular dyad to investigate electronic energy transfer (EET) along proline chains. The research found high EET efficiency (80-90%) between pyrene and perylene, influenced by proline conformation and solvent polarity.

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Area of Science:

  • Supramolecular Chemistry
  • Photophysics
  • Organic Synthesis

Background:

  • Understanding electronic energy transfer (EET) in molecular systems is crucial for developing advanced materials.
  • Oligo-proline chains offer a unique scaffold for mediating EET due to their conformational flexibility and defined structure.
  • Investigating the influence of conformation and solvent on EET dynamics is essential for controlling energy flow.

Purpose of the Study:

  • To synthesize and characterize a molecular dyad (PY-P8-PER) for studying EET along an oligo-proline chain.
  • To elucidate the conformational dynamics of the oligo-proline spacer and its impact on EET.
  • To quantify the efficiency and rate of intramolecular EET between pyrene and perylene terminals.

Main Methods:

  • Synthesis of a PY-P8-PER molecular dyad and a pyrene-based control compound.
  • Spectroscopic analysis including N-H NMR, Circular Dichroism (CD), steady-state, and time-resolved fluorescence spectroscopy.
  • Computational studies using Density Functional Theory (DFT) and distributive modeling.

Main Results:

  • The PY-P8-PER dyad exhibits efficient intramolecular EET from pyrene to perylene (80-90% probability).
  • Oligo-proline conformation (all-trans in methanol) and solvent polarity influence amide isomerism (cis/trans) and stabilize specific structures.
  • EET rates are consistent across a narrow range of conformers, as evidenced by time-resolved spectroscopy and DFT calculations.

Conclusions:

  • The PY-P8-PER dyad effectively demonstrates EET along an oligo-proline linker, with efficiency modulated by conformational states.
  • Amide isomerism within the proline chain plays a significant role in dictating the overall EET dynamics.
  • The study provides a framework for designing molecular systems with controlled energy transfer pathways based on proline scaffolds.