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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Subtle "supramolecular buttressing effects" in Cucurbit[7]uril/guest assemblies.

Roymon Joseph¹, Eric Masson

¹Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA.

Organic & Biomolecular Chemistry

|April 5, 2013

Summary

This study introduces "supramolecular buttressing," where neighboring groups influence substituent effects in molecular recognition. Despite conformational changes, biphenyl derivatives showed minimal binding affinity changes with Cucurbit[7]uril.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

Supramolecular Chemistry
Host-Guest Chemistry
Organic Chemistry

Background:

The
supramolecular buttressing
concept proposes that adjacent molecular units can alter substituent effects on intermolecular recognition.

Purpose of the Study:

To synthesize and investigate biphenyl derivatives with varying 4-substituents (H, F, CH3) to probe the
supramolecular buttressing
effect on host-guest interactions with Cucurbit[7]uril (CB[7]).

Main Methods:

Synthesis of biphenyl derivatives with 3-dimethylsulfonium and varied 4-substituents.
Conformational analysis of free biphenyl species.
Host-guest binding studies with Cucurbit[7]uril (CB[7]).

Main Results:

4-Substituents influenced the syn/anti conformations of the 3-dimethylsulfonium groups.
The
supramolecular buttressing
model was validated as conformations affected guest positioning within CB[7].
Binding affinities towards CB[7] were unexpectedly insensitive to 4-substituent variations and sulfonium conformations, with solvation playing a key role.

Conclusions:

The study validates the
supramolecular buttressing
concept in modulating molecular conformations.
Host-guest binding affinities were less affected than anticipated, highlighting the significant role of solvation in dampening electrostatic interactions.