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If we dip a sample of chloroalkane in an ethereal solution, radicals form at the sites where chlorines are attached, which subsequently pair with other radicals.

Now, consider 1,3,5-trichlorobenzene:

enter image description here

If I attempted to perform a Wurtz-Fittig reaction with this, I suspect the product would be a two dimensional polymerised product. I drew a portion of it:

enter image description here

This polymer is quite interesting. Has this been observed before? Does it have a name?

While looking for the name of this molecule is my primary concern, it would be great if I could also get some information about its properties. This polymer looks like a "hollow" version of graphene, so I believe this would have some properties of graphene, although quite lighter. I think this could conduct electricity, due to conjugated $\pi$ systems of benzene rings. I also believe it would be quite porous, and probably allow small molecules like $\ce{H2O}$ to pass through.

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    $\begingroup$ Fittig isn't particularly good coupling reaction. Ultrasounds are needed even for biphenyls. $\endgroup$
    – Mithoron
    Jun 9, 2017 at 14:01
  • $\begingroup$ @Mithoron thanks for your insight, but my main concern is with the polymer itself. If Fittig isn't good enough, how about Kolbe electrolysis of trisodium 1,3,5-benzenetricarboxylic acid? Anything that can give me my polymer. $\endgroup$
    – Pritt says Reinstate Monica
    Jun 10, 2017 at 4:03
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    $\begingroup$ I think it simply can't be done with state-of-art methods. Interesting idea though. Problem is that even if you used Suzuki (no Kolbe wouldn't do) there would be nothing to force planarity and order. $\endgroup$
    – Mithoron
    Jun 10, 2017 at 11:45
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    $\begingroup$ Not "allows", rings create ring current, and no, no, no. $\endgroup$
    – Mithoron
    Jun 10, 2017 at 18:34
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    $\begingroup$ The first coupling will already be so far out of planarity, it is a biphenyl after all, that there would never be a 2D-structure. I believe with the third molecule the whole thing will start to coil. My best guess would be that there might be string-like oligomers. $\endgroup$
    – Martin - マーチン ♦
    Mar 30, 2022 at 22:03

2 Answers 2

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I think that the IUPAC nomenclature is not yet ready to name such regular periodic network structures. The IUPAC polymer nomenclature could be used to name it, but the meaning of the following names (source- and structure-based) are more or less vague, respectively:

  • net-poly(benzene)
  • net-poly(benzene-1,3,5-triyl)

(The latter name might be exact, maybe even just “poly(benzene-1,3,5-triyl)”, but the polymer nomenclature for network polymers does not expect such regular branching with the branch size of the monomer unit, or say regular trivalent monomer based mesh networks. IUPAC ‘Purple Book’ does not mention such regular networks, there are some polymers based on benzene-1,2,4,5-tetrayl unit, but these are linear strands; and also benzene-1,3,5-triyl unit, but as a center branching point of three-star polymer, where the rest are three polystyrene chains.
And there is also seemingly appropriate comb- prefix available, but it's something different, is not meant for such networks.)

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Ignoring the complex challenges it would take to make such a structure, the name is rather unclever with the literature referring to it as "holey graphene". You could probably take this a step further with your hypothetical material and call it :

  • well-ordered holey graphene
  • or better yet, well-ordered monodisperse-C6-holey graphene.

with C6 alluding to the missing $\ce{C6}$ ring that would be present in perfect graphene. Materials science has very unrigid naming conventions. If you make it first, you can greatly influence the literature terms.

As far as conductivity goes, I agreed that it would likely be conductive or semi-conductive at a minimum similar to poly(9,10-anthracene diylidene).

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    $\begingroup$ I actually couldn't find any evidence that holey graphene would be saturated with hydrogen at the edges of the holes. Sometimes functional groups though. Anyway, I did not really look deep into the matter. $\endgroup$
    – Martin - マーチン ♦
    Mar 30, 2022 at 21:59

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