Aqueous compatible supramolecular materials hold promise for applications in environmental remediation, energy harvesting and biomedicine. One remaining challenge is to actively select a target structure from a multitude of possible options, in response to chemical signals, while maintaining constant, physiological conditions. Here, we demonstrate the use of amino acids to actively decorate a self-assembling core molecule in situ, thereby controlling its amphiphilicity and consequent mode of assembly. The core molecule is the organic semiconductor naphthalene diimide, functionalized with D- and L- tyrosine methyl esters as competing reactive sites. In the presence of α-chymotrypsin and a selected encoding amino acid, kinetic competition between ester hydrolysis and amidation results in covalent or non-covalent amino acid incorporation, and variable supramolecular self-assembly pathways. Taking advantage of the semiconducting nature of the naphthalene diimide core, electronic wires could be formed and subsequently degraded, giving rise to temporally regulated electro-conductivity.

与水相容的超分子材料有望用于环境修复，能量收集和生物医学中。剩下的一项挑战是在保持恒定的生理条件的同时，响应化学信号从多种可能的选择中主动选择目标结构。在这里，我们证明了使用氨基酸主动修饰原位自组装核心分子，从而控制其两亲性和随后的组装方式。核心分子是被D-和L官能化的有机半导体萘二酰亚胺-酪氨酸甲酯作为竞争性反应位点。在α-胰凝乳蛋白酶和选定的编码氨基酸的存在下，酯水解和酰胺化之间的动力学竞争导致共价或非共价氨基酸的结合以及可变的超分子自组装途径。利用萘二酰亚胺核的半导体性质，可以形成电线并随后使其降解，从而产生了时间上可调节的导电性。