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Science 19 May 2006:
Vol. 312. no. 5776, pp. 1030 - 1034
DOI: 10.1126/science.1124621
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Reports

Preparation of Poly(diiododiacetylene), an Ordered Conjugated Polymer of Carbon and Iodine

Aiwu Sun, Joseph W. Lauher, Nancy S. Goroff*

Conjugated organic polymers generally must include large substituents for stability, either contained within or appended to the polymer chain. In polydiacetylenes, the substituents fulfill another important role: During topochemical polymerization, they control the spacing between the diyne monomers to produce an ordered polymer. By using a co-crystal scaffolding, we have prepared poly(diiododiacetylene), or PIDA, a nearly unadorned carbon chain substituted with only single-atom iodine side groups. The monomer, diiodobutadiyne, forms co-crystals with bis(nitrile) oxalamides, aligned by hydrogen bonds between oxalamide groups and weak Lewis acid-base interactions between nitriles and iodoalkynes. In co-crystals with one oxalamide host, the diyne undergoes spontaneous topochemical polymerization to form PIDA. The structure of the dark blue crystals, which look copper-colored under reflected light, has been confirmed by single-crystal x-ray diffraction, ultraviolet-visible absorption spectroscopy, and scanning electron microscopy.

Department of Chemistry, State University of New York, Stony Brook, NY 11794–3400, USA.

* To whom correspondence should be addressed. E-mail: nancy.goroff{at}sunysb.edu

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Science. ISSN 0036-8075 (print), 1095-9203 (online)