Evolution of mind in eusocial insects or Mullocs

Imagine if you will the squid with its chemoreceptors combined with a physical neurotransmitter connected to another squid I.E the two squid could actually use their tentacles to link their nervous systems.
This would evolve through sex as some squid display complex patterns of chemoreception combined with visual chromatophore communication.

Click to access a222648.pdf

Social Insect reproduction as we know it on earth involves reproduction by the one or the few and the sexual evolution of my proposed neural connectivity would not evolve among the haplodiploidy of the eusocial insects.

Our world eons ago had for a while a high oxygen atmosphere in which very large insects evolved it’s this perhaps that would enable the evolution of larger brains,so it’s no accident that larger brains did evolve among the cephalopods as the water medium allows for a greater oxygen exchange.
larger insects in a high Oxygen world would still have to overcome the haplodiploidy barrier to evolving sexualy inabling neuroconnectivity between individuals.
Evolution does not plan anything so what would be required to transfer large amounts of information between neurologically connected beings and what would be the environmental factors that would favor evolving this?

This post in response to this post on Centauri Dreams;   Can Social Insects Have a Civilization?

EDIT 4 Jan 2016

My Blog post that discussed Oxygen rich waters and large cephalopods that neurologically connected together with an evolved reproductive tentacle was chosen in the hope that intelligence and “civilization” maybe requires “consciousness”
This so called emergent property is something that is not clear to me would exist in AI or Von Neumann machines so perhaps it is possible to have a civilization of small social insects(low oxygen world) that would appear to us as a civilization(recognize this theory? ) After all if the AI and Von Neumann machines are advanced(evolving) software without self awareness then civilization does not need this treat to come about.
So how to bring about the cephalopod emergent property?
(A)(1) The tentacle reproductive organ or hectocotylus could evolve to make synaptic connects with the other organism
(A)(2) in some cephalopods the hectocotylus is left inside the female so imagine a hectocotylus with one of the males brain lobs inside.
(A)(3) this would be a slow thinking superorganism augmented by communication of the skin coloration patterns.