List segmentation and Dynamic content

I have an email with dynamic content, I need to send it to people that have different business units, so for instance, person A belongs to two different business units with the logo being dynamic, I need to send them both versions of the email.  If I create segmented list based off the business unit, then create a smart list based on that segment, will it send both versions of the email to the same address or will Marketo dedupe it at the send?  If it dedupes at the send would it work if I do two sends with different smartlists calling out the different business units?  Or is there another way without having to create multiple emails for the different business units?