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Synthesis

Iododiacetylene polymer may lead to 'linear carbon'

May 22, 2006 | A version of this story appeared in Volume 84, Issue 21

Polydiacetylenes are useful optoelectronic materials, but the conjugated polymers are tricky to make because they require bulky substituents to stabilize against explosive decomposition and to produce an ordered polymer structure. Thus, cocrystallizing the monomer with a spacer compound is a common synthetic route. In the latest twist on this approach, Aiwu Sun, Joseph W. Lauher, and Nancy S. Goroff at the State University of New York, Stony Brook, have synthesized a novel bis(nitrile) oxalamide spacer and used it to make poly(diiododiacetylene), or PIDA (shown), a conjugated carbon chain adorned only with iodine side groups (Science 2006, 312, 1030). The oxalamide groups, −NHCOCONH−, form a hydrogen-bonded network, whereas the terminal nitriles, −(CH2)4CN, form weak Lewis acid-base pairs with the iodine atoms of the butadiyne monomer, IC≡CC≡CI. The resulting molecular scaffold aligns the monomers, prompting spontaneous polymerization. PIDA is a potential precursor to substituted polydiacetylenes, and it could lead to carbyne, a long-sought hypothetical linear sp-hybridized carbon allotrope, if the iodine atoms can be removed.

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