PCOT and COT

PCOT, in terms of electron sequestering power, is the strongest organic oxidizing agent known to mankind! This is a result of several synergistic attributes: 1. The center ring is a cyclooctatetraene (COT) ring sytem; 2. The tetraanulation (four cyclobuta groups) renders the COT flat as a pancake; 3. The planar COT is antiaromatic and in need of two electrons; and 4. All 16 fluorine atoms are electron withdrawing, hence, dramatically further increasing the natural anti-aromatic electron hunger of this molecule.

The solution electron affinity of the simple unsubstituted COT is quite high itself, as evidenced by the cyclovoltamitry data that we have previously published. When Willstater first synthesized COT, he was quite dissapointed, because he did not find another plana aromatic, benzene like, molecule. Instead the system is pucked up like a tub. Years later it was found that two electrons could easily be added to COT to render it planar and aromatic.

Due to its uniquely large electron affinity PCOT serves pragmatically as a cathode system in batteries.  Its oxidation potential is so high that it can "suck" its two electrons needed for aromaticity from very inactive metals, such as mercury. There is no need (that we know of) for a mercury anode battery but proof of principle of such is interesting and in hand. Its electronic properties are sufficiently valuable to make it a "game changer" for a number of commercial applications.

Fortunately, we have found the synthesis of PCOT was origonally worked out by Soulen and Park in the early 70s. It has since been improved upon, by us and others, and PCOT can now be synthesized cheaply and without stress from a simple refrigerant. There is no reason that this synthetic procedure could not be scaled up to yield a commercially viable product. See below: