All minerals have two ways they "break" - fractures, and cleavage.
Fractures occur at almost any location, and follow no particular pattern. Diamond is VERY hard to fracture, but it does occur with high amounts of pressure, and/or defects in the material. (Toughness rating of excellent)
Cleavage is where the mineral will naturally seperate based on the molecular structure of said mineral. Diamond has four planes of cleavage. Along said planes of cleavage, Diamond is no tougher than glass (toughness rating of fair).
Jewelery makers can accidently chip/break diamonds while putting them into rings and other jewelry by accidently applying too much pressure (by hand, no less) along one of these planes of cleavage.
With careful application, you can imbed diamond into other materials to make a rough surface (like our modern diamond saws and drills). Anywhere where pressure is applied along a plane of cleavage though, the diamond will simply break off. (This is also why diamond blades and drills do not last forever).
So yes, you could imbed diamond into something, but it doesn't make a very viable piece of armor. It can make a decent grinding surface, but makes a poor cutting surface (ie - a single plane which you cut with, like a knife).
Diamond is a very resilient material, but only in specific applications.