Department of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.
Department of Chemistry , University of Massachusetts - Amherst , Amherst , Massachusetts 01003 , United States.
J Am Chem Soc. 2019 Nov 13;141(45):18048-18055. doi: 10.1021/jacs.9b06852. Epub 2019 Nov 1.
Interfacial chemistry provides an opportunity to control dynamic materials. By harnessing the dynamic covalent nature of imine bonds, emulsions are generated in situ, predictably manipulated, and ultimately destroyed along liquid-liquid and emulsion-solid interfaces through simple perturbation of the imine equilibria. We report the rapid production of surfactants and double emulsions through spontaneous in situ imine formation at the liquid-liquid interface of oil/water. Complex double emulsions with imine surfactants are stable to neutral and basic conditions and display dynamic behavior with acid-catalyzed hydrolysis and imine exchange. We demonstrate the potential of in situ imine surfactant formation to generate complex surfactants with biomolecules (i.e., antibodies) for biosensing applications. Furthermore, imine formation at the emulsion-solid interface offers a triggered payload release mechanism. Our results illustrate how simple, dynamic interfacial imine formation can translate changes in bonding to macroscopic outputs.
界面化学为控制动态材料提供了机会。通过利用亚胺键的动态共价性质，乳液可以在原位生成，并通过简单地扰动亚胺平衡来进行可预测的操作，最终在液-液和乳液-固界面处破坏。我们报告了通过在油/水的液-液界面处原位形成亚胺来快速制备表面活性剂和双乳液。具有亚胺表面活性剂的复杂双乳液在中性和碱性条件下稳定，并表现出酸催化水解和亚胺交换的动态行为。我们证明了原位亚胺表面活性剂形成的潜力，可以为生物传感应用生成具有生物分子（例如抗体）的复杂表面活性剂。此外，乳液-固界面处的亚胺形成提供了一种触发式有效负载释放机制。我们的结果说明了简单的动态界面亚胺形成如何将键的变化转化为宏观输出。
