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Metallopolymers Featuring Boratabenzene Iron Complexes

  1. Dr. Frank Pammer,
  2. Prof. Roger A. Lalancette,
  3. Prof. Frieder Jäkle*

Article first published online: 26 AUG 2011

DOI: 10.1002/chem.201101109

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 17, Issue 40, pages 11280–11289, September 26, 2011

Additional Information

How to Cite

Pammer, F., Lalancette, R. A. and Jäkle, F. (2011), Metallopolymers Featuring Boratabenzene Iron Complexes. Chem. Eur. J., 17: 11280–11289. doi: 10.1002/chem.201101109

Author Information

  1. Department of Chemistry, Rutgers University-Newark, 73 Warren Street, Newark, NJ 07102 (USA), Fax: (+1) 973-353-1264

*Department of Chemistry, Rutgers University-Newark, 73 Warren Street, Newark, NJ 07102 (USA), Fax: (+1) 973-353-1264

Publication History

  1. Issue published online: 16 SEP 2011
  2. Article first published online: 26 AUG 2011
  3. Manuscript Received: 11 APR 2011

Funded by

  • Alexander von Humboldt foundation
  • National Science Foundation. Grant Numbers: NSF CHE-0809642, NSF CRIF-0443538

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Keywords:

  • boratabenzene;
  • boron;
  • click chemistry;
  • iron;
  • metallopolymers;
  • polymerization

Abstract

Boratabenzene-derived metallocene analogues are introduced as versatile new building blocks for metallopolymers. Bis(borinato)iron(II) complexes of the type Fe(C5H5B[BOND]R)2 (R: C[TRIPLE BOND]CH, C[TRIPLE BOND]CSiMe3, 4-(1-benzyl-1,2,3-triazolyl) were synthesized and spectroscopically, structurally, and electrochemically characterized. Polymerization via Sonogashira–Hagihara coupling of the alkynyl-substituted derivative Fe(C5H5B[BOND]C[TRIPLE BOND]CH)2 with 2,5-bis(dodecyloxy)-1,4-diiodobenzene yields a film-forming polymer in 50–69 % yield. Polymer batches were obtained with number-average molecular weights (Mn) of 11.7 and 20.5 kDa and polydispersity indices (PDI) of 1.55 and 2.65, respectively, as determined by gel permeation chromatography relative to polystyrene standards. Click-type polymerization of Fe(C5H5B[BOND]C[TRIPLE BOND]CH)2 through azide–alkyne cycloaddition with 1,4-bis(4-azidobutoxy)benzene gives the corresponding metallopolymer with an Mn of 5.7 kDa and a PDI of 2.29 in 87 % yield.

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