From what I can see he wants to appeal more to the r&b/hip hop audience but I still can't see it happening, no matter how many rappers he hangs around with. I don't listen to radio much these days, but I can't imagine his songs being played on urban radio at all.
They won't - yet. What he's doing is positioning/re-inventing himself as a rap type badass 'artist' with street cred because wholesome cherub didn't work, only had limited appeal.
It's a ruse in the hope of broadening his fanbase imo. It might be a vain hope but it's working in some ways as he's becoming quite notorious and the badboy press serves this image. The next step is music to match.
It might not work. But that's what they're aiming for imo.