No. 
 

It isn’t mentioned here:

https://support.sonos.com/en-us/article/set-up-your-sonos-sub

You could split the Pair and put one Sub on each.

“Some Sonos home theater speakers can connect with up to two Subs.”

That only applies to soundbars. 

FYI, splitting the pair will require you to set up a separate room for each speaker ( even though they are physically in the same space). You’ll have to group them together to play as one. You can setup a permanent group in the app. Doing the above will no-longer be true stereo separation as both speakers will play left and right channels. If you use Trueplay you’ll have to do it separately for each speaker or just use Auto tuning for both rooms..

Any chance to sync (2) era 100 & (2) sub gen 4 ?

No, there is no setup in Sonos, other than a home theater setup, which can accept two Subs in a single room. 

As suggested above, you could set up the two Era 100s as separate rooms, and associate a Sub with each device.