This is very interesting discussion. I also would like to be able to use Tkinter modules but current version of IronPython does not support it. In fact we have today latest version IronPython 2.7.7rc2 I can see that works started on IronPython 3. Unfortunately not much progress happening right now.
We are trying to get a good final 2.7 release out and then will be focusing on IronPython3. I would hope to have something usable by the end of the year (there are many changes we need to implement).