Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands

Blayne M. McKenzie, Adriane K. Miller, Rudy J. Wojtecki, J. Casey Johnson, Kelly A. Burke, Karis A. Tzeng, Patrick T. Mather, Stuart J. Rowan

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A versatile one-pot synthetic platform for the preparation of a range of functionalized 2,6-bisbenzimidazolylpyridine (Bip) derivatives is presented. This protocol significantly reduces the cost and time of previous synthetic routes, while facilitating scale up to multi-gram quantities in good yields (63-90%). The previous synthetic methodology was improved through judicious choice of the reducing agent and solvent in the reduction/ring-closing step. Via this platform, we also successfully accessed a mesogenic Bip ligand and herein report initial liquid crystalline properties of this derivative.

Original languageEnglish
Pages (from-to)8488-8495
Number of pages8
JournalTetrahedron
Volume64
Issue number36
DOIs
Publication statusPublished - 2008 Sep 1
Externally publishedYes

Fingerprint

Reducing Agents
Ligands
Derivatives
Costs and Cost Analysis
Crystalline materials
Liquids
Costs

Keywords

  • Liquid crystal
  • Metal-ligand coordination
  • Supramolecular chemistry
  • Terdentate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

McKenzie, B. M., Miller, A. K., Wojtecki, R. J., Johnson, J. C., Burke, K. A., Tzeng, K. A., ... Rowan, S. J. (2008). Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands. Tetrahedron, 64(36), 8488-8495. https://doi.org/10.1016/j.tet.2008.05.075

Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands. / McKenzie, Blayne M.; Miller, Adriane K.; Wojtecki, Rudy J.; Johnson, J. Casey; Burke, Kelly A.; Tzeng, Karis A.; Mather, Patrick T.; Rowan, Stuart J.

In: Tetrahedron, Vol. 64, No. 36, 01.09.2008, p. 8488-8495.

Research output: Contribution to journalArticle

McKenzie, BM, Miller, AK, Wojtecki, RJ, Johnson, JC, Burke, KA, Tzeng, KA, Mather, PT & Rowan, SJ 2008, 'Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands', Tetrahedron, vol. 64, no. 36, pp. 8488-8495. https://doi.org/10.1016/j.tet.2008.05.075
McKenzie BM, Miller AK, Wojtecki RJ, Johnson JC, Burke KA, Tzeng KA et al. Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands. Tetrahedron. 2008 Sep 1;64(36):8488-8495. https://doi.org/10.1016/j.tet.2008.05.075
McKenzie, Blayne M. ; Miller, Adriane K. ; Wojtecki, Rudy J. ; Johnson, J. Casey ; Burke, Kelly A. ; Tzeng, Karis A. ; Mather, Patrick T. ; Rowan, Stuart J. / Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands. In: Tetrahedron. 2008 ; Vol. 64, No. 36. pp. 8488-8495.
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