Aromaticity of 1,1'-bi(cycloprop-2-en-1-ylidene) and 1,4-dioxine

Are these Anti aromatic/aromatic or non aromatic?


1.


![1,1'-bi(cycloprop-2-en-1-ylidene)](https://i.gyazo.com/ca85ac5f83131012a14bf0fb300828e1.png)


Here, if we were to consider the resonating structure(s) with charge separation


![](https://i.gyazo.com/4d900097f7422a377c50615b79028e77.png)


One ring is aromatic and other is anti aromatic, and secondly there is not continuous delocalization of pi electrons between those rings {if we don't include no resonating structures with no formal charges, as their contribution would not be equalish to normal form} what category would this go in?


2.


![1,4-dioxine](https://i.gyazo.com/d3d5602b4c6dd46654c1affde33c4b05.png)


Like before, there can be no continuous electron delocalization like stated in previous example , only other ones the diff forms of 


![](https://i.gyazo.com/c34026f36ea09e71819a9016aed254b0.png)


If we consider it to have enough delocalization, it would have 4n electrons and hence antiaromatic {although all the orbitals wont be mixed as 3 on each side twice with oxygen's lone pair being common between all of them}


3. As we can see in pyrene, if we consider central double bond to be non participating, huckle rule works, is there a better (and just by observation by eye) method that we could use for multi ring systems? what is the basic condition for aromaticity besides planar,cyclic,sp2 {nitrogen and oxygen in general change their hybridisation as to make it aromatic with their lone pair(s)}




Antiaromaticity is a fictional state with real consequences, that any molecule will distort to avoid.


In the case of molecule 1, the primary state will be a triplet (unpaired pi-electrons), with the central bond lengthening to decrease the pairing of the pi-electrons. This will lead to 3 electrons in each pi-system, and hence preventing antiaromaticity, because there are no longer 4n electrons in the rings. A fictional molecule, with the constituency shown for molecule 1 that is in a singlet state would be antiaromatic.


In the case of molecule 2, the molecule will distort itself to make the at least one of the oxygens non-coplanaer with the pi-system, and no longer being co-planar, the system will not be antiaormatic. A fictional molecule with the constituency shown for molecule 2 that is co-planar, would be antiaromatic.


It is unclear what you are asking about for pyrene.


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