Metallopolymers featuring boratabenzene iron complexes

Frank Pammer; Roger A. Lalancette; Frieder Jäkle

doi:10.1002/chem.201101109

Metallopolymers featuring boratabenzene iron complexes

Frank Pammer, Roger A. Lalancette, Frieder Jäkle

Rutgers Newark, Chemistry

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

Boratabenzene-derived metallocene analogues are introduced as versatile new building blocks for metallopolymers. Bis(borinato)iron(II) complexes of the type Fe(C₅H₅B-R)₂ (R: C≡CH, C≡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-C≡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 (M_n) 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(C₅H ₅B-C≡CH)₂ through azide-alkyne cycloaddition with 1,4-bis(4-azidobutoxy)benzene gives the corresponding metallopolymer with an M_n of 5.7 kDa and a PDI of 2.29 in 87 % yield.

Original language	English (US)
Pages (from-to)	11280-11289
Number of pages	10
Journal	Chemistry - A European Journal
Volume	17
Issue number	40
DOIs	https://doi.org/10.1002/chem.201101109
State	Published - Sep 26 2011

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis
Organic Chemistry

Keywords

boratabenzene
boron
click chemistry
iron
metallopolymers
polymerization

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10.1002/chem.201101109

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abstract = "Boratabenzene-derived metallocene analogues are introduced as versatile new building blocks for metallopolymers. Bis(borinato)iron(II) complexes of the type Fe(C5H5B-R)2 (R: C≡CH, C≡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-C≡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(C5H 5B-C≡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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AU - Lalancette, Roger A.

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KW - click chemistry

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KW - metallopolymers

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Metallopolymers featuring boratabenzene iron complexes

Abstract

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Keywords

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