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Updated: Sep 24, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Programming Rapid Functional Group Diversification into a Solid-State Reaction: Aryl Nitriles for Self-Assembly,
Changan Li1, Dale C Swenson1, Leonard R MacGillivray1
1Department of Chemistry, University of Iowa, Iowa City, IA, 52242-1294, USA.
Abstract:
A method to rapidly diversify the molecules formed in organic crystals is introduced, with aryl nitriles playing a novel dual role as both hydrogen-bond acceptors and modifiable organic groups. The discovery of coexisting supramolecular synthons in the same crystal is also described. The general concept is demonstrated by using a bis(aryl nitrile) alkene that undergoes a hydrogen-bond-directed intermolecular [2+2] photodimerization to form a tetra(aryl nitrile)cyclobutane. The product is readily converted by click reactivity to a tetra(aryl tetrazole) and by hydrolysis to a tetra(aryl carboxylic acid). The integration of aryl nitriles into solid-state reactions opens broad avenues to post-modify products formed in crystalline solids for rapid diversification.
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