Kinetically controlled simplification of a multiresponsive [10 × 10] dynamic imine library

Abstract

Kinetically controlled self-sorting processes in complex synthetic mixtures represent an important model for behaviours of biological networks, which operate far from equilibrium and without interference among simultaneous metabolic pathways. However, most of the previously reported kinetic self-sorting protocols dealt with small dynamic libraries and a single external stimulus. Here, we report the iterative simplification of a large imine dynamic combinatorial library (DCL) constructed from 10 aldehydes and 10 anilines, under the sequential influence of an oxidant, an adsorbent, and an increase in temperature. Six components of this initial DCL are mechanically isolated and amplified at least three-fold relative to their equilibrium distributions at the outset of the sorting process.