Winform in Web Form

Question

I am creating an Instant Messenger web-based application. I managed to display the roster in a gridview.When i click on any name, i want to display a chat box so i can send and receive messages.To implement this, i think of 2 things

1. create popup window using win.open()
2. create and call a class using System.Windows.Forms and related objects.

I used the 2nd option . I customized it and it works.

Question
1. Does using and and calling winform in web app create problem in the future. (during deployment?)
2. What object can i used to replace it. I want the functionality of winform but have no idea bout possible limitations.. thanks