Do there exist aromatic compounds similar to azulene?
There is this compound which is I believe the closest to anything which you've asked for.
Except the fused part this satisfies all your conditions.
In a polar solvent the double bond breaks to form two highly stable aromatic rings(tropylium and dicyclopentene) which act as two separate poles. It also lowers the rotation barrier of this compound. Hence it even becomes soluble. Along with azulene this is as close as an organic compound gets to being ionic.