Single-crystal-to-single-crystal topochemical polymerizations by design

Accounts of Chemical Research
Joseph W LauherNancy S Goroff

Abstract

The polymerization of simple conjugated dienes has long been of interest: polydienes occur throughout Nature, and polyisoprene and its analogues form the basis of entire industries. In contrast, the polymers of similar small conjugated compounds, diacetylenes, trienes, and triacetylenes, are either unknown or laboratory curiosities. For 40 years, the only viable synthetic method for the 1,4-polymerization of a diacetylene was a topochemical polymerization in a condensed phase. But such an approach is hit or miss: if the diacetylene monomers have a solid-state structure preorganized at distances matching the repeat distance in the final polymer, then thermal or photochemical energy can bring about the polymerization. However, most monomers lack the proper structural parameters and simply do not react. As discussed in this Account, we have developed a supramolecular host-guest strategy that imposes the necessary structural parameters upon a diacetylene monomer that otherwise does not polymerize. We apply this strategy in the synthesis of new types of conjugated polymers made from diacetylenes, triacetylenes, and trienes. To implement the host-guest strategy, we chose a host that would self-assemble into a supramolecular structure...Continue Reading

References

Jul 24, 2001·Chemistry : a European Journal·P Metrangolo, G Resnati
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Sep 5, 2002·Journal of the American Chemical Society·Tram HoangFrank W Fowler
May 7, 2005·Organic Letters·Nancy S GoroffJoseph W Lauher
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Mar 14, 2008·Journal of the American Chemical Society·Christopher WilhelmJeffrey A Webb
May 21, 2008·Journal of the American Chemical Society·Liang LuoNancy S Goroff

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Citations

Oct 10, 2013·ACS Applied Materials & Interfaces·Thierry BarisienClémence Allain
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