Hello,
Yes, it is possible but you can do it manualy like previous solution (http://devnet.kentico.com/questions/separate-mails-to-different-receivers). To create PDF in c# you need to use another c# librarby like PDFsharp. When you create file you can easly attach it to email :)
EDIT: Here's quick use of this library http://csharp.net-informations.com/file/create-pdf.htm