Encapsulation of reactive agents embedded within a matrix is the most studied concept to develop self-healing materials. The most common approaches employ either a single component with catalyst dispersed in the matrix or a single environment-reactive component for corrosion protection [1]. Recently an approach for corrosion protection based on a single reactive healing agent that combines wetting, reactivity with ambient humidity and the underlying metallic surface, hydrophobicity and densification in time was proposed [2]. Following this idea of using silyl esters, Huang et al. developed a similar system where 1H,1H,2H,2H-perfluorooctyltriethoxysilane (POTS) was used in place of a silyl ester [3]. Despite the good results offered by the octyldimethylsilyl ester and the POTS, there is room for improvement in the design of the healing agents employed for corrosion protection. The goal of this research is to better understand the wetting, barrier and densification properties of silane based healing agents to be able to develop efficient single reactive healing agents. Therefore a selection of silanes with different chemical backbone structure and surface-reactive end group is evaluated. The barrier properties and the hydrophobicity of the agents is investigated to gain insight into the relationship between chemical structure and final thin film properties. Moreover, in order to evaluate the time dependent corrosion protection performance of the different healing agents a novel optical-electrochemical analysis technique has been developed.