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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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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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Molecular puzzle ring: pseudo[1]rotaxane from a flexible cyclodextrin derivative.

Atsuhisa Miyawaki1, Paul Kuad, Yoshinori Takashima

  • 1Department of Macromolecular Science, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan.

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Researchers studied pseudo[1]rotaxanes using flexible cyclodextrin derivatives. The size and shape of bulky end groups on these molecules control the self-inclusion kinetics and enhance stability.

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Kinetics

Background:

  • Pseudo[1]rotaxanes are supramolecular structures formed by threading a guest molecule into a macrocycle.
  • Cyclodextrin (CD) derivatives offer tunable properties for host-guest complexation.

Purpose of the Study:

  • To investigate the kinetic quantitation of pseudo[1]rotaxane formation.
  • To understand the role of bulky end groups in the self-inclusion process and stability.

Main Methods:

  • Synthesis of cyclodextrin derivatives (1-R) with cinnamamide guest and various end groups (R).
  • Kinetic analysis of self-inclusion complex formation.
  • Conformational analysis of altrose within the cyclodextrin cavity.

Main Results:

  • The size and shape of the bulky end group (R) dictate the kinetics of pseudo[1]rotaxane formation.
  • Specific derivatives (1-Ad and 1-Me) formed self-inclusion complexes via conformational conversion of altrose.
  • The flexible altro-alpha-CD cavity exhibited an induced fit mechanism for the arm moiety.

Conclusions:

  • Bulky end groups are crucial for controlling the rate and stability of pseudo[1]rotaxane formation.
  • The flexibility of the cyclodextrin cavity plays a key role in accommodating the guest moiety.
  • Induced fit mechanisms enhance the stability of these supramolecular assemblies.