Multifaceted and route-controlled "click" reactions based on vapor-deposited coatings

"Click" reactions provide precise and reliable chemical transformations for the preparation of functional architectures for biomaterials and biointerfaces. The emergence of a multiple-click reaction strategy has paved the way for a multifunctional microenvironment with orthogonality and precise multitasking that mimics nature. We demonstrate a multifaceted and route-controlled click interface using vapor-deposited functionalized poly- para -xylylenes. Distinctly clickable moieties of ethynyl and maleimide were introduced into poly- para -xylylenes in one step via a chemical vapor deposition (CVD) copolymerization process. The advanced interface coating allows for a double-click route with concurrent copper( i )-catalyzed Huisgen 1,3-dipolar cycloaddition (CuAAC) and the thiol-maleimide click reaction. Additionally, double-click reactions can also be performed in a cascade manner by controlling the initiation route to enable the CuAAC and/or thiol-yne reaction using a mono-functional alkyne-functionalized poly- para -xylylene. The use of multifaceted coatings to create straightforward and orthogonal interface properties with respect to protein adsorption and cell attachment is demonstrated and characterized. Multifaceted and route-controlled click reactions are realized using functionalized poly- para -xylylene coatings, and the concurrent display of orthogonal interface properties is demonstrated.