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Synthesis and Polymerization Behavior of Tridentate Diacetylene Hosts

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Abstract

The synthesis of three new tridentate ligands capable of forming large cavities for encapsulation of organoiodides is described. Each compound consists of a central heterocyclic “base unit” linked by acetylenes to two heterocyclic “arm” units. The base and the arm unit are each either a 2,6-disubstituted pyridine or a 2,5-disubsituted thiophene ring. The terminal end of each arm unit is connected to a (butoxycarbonyl)methylurethanyl (BCMU) moiety by way of a diacetylene linkage. This serves as a polymerogenic group that helps align the diacetylenes for topotactic polymerization. The triaryl ring systems are constructed through a series of aryl bromide/protected acetylene coupling steps, followed by deprotection and further coupling. Two of the compounds polymerize photochemically and all three polymerize thermally.

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Authors and Affiliations

  1. Department of Chemistry, Hunter Chemistry Laboratories, Clemson University, Clemson, SC, 29634, USA

    Brian T. Holmes & William T. Pennington

  2. Department of Chemistry, Furman University, Greenville, SC, 29613, USA

    Prasant Deb & Timothy W. Hanks

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  1. Brian T. Holmes
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  2. Prasant Deb
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  3. William T. Pennington
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  4. Timothy W. Hanks
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Correspondence to Timothy W. Hanks.

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Holmes, B.T., Deb, P., Pennington, W.T. et al. Synthesis and Polymerization Behavior of Tridentate Diacetylene Hosts. J Polym Res 13, 133–144 (2006). https://doi.org/10.1007/s10965-005-9015-9

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  • DOI: https://doi.org/10.1007/s10965-005-9015-9

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