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

doi:10.1016/j.tet.2008.05.075

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

Department of Biomedical & Chemical Engineering

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

28 Scopus citations

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 language	English (US)
Pages (from-to)	8488-8495
Number of pages	8
Journal	Tetrahedron
Volume	64
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2008.05.075
State	Published - Sep 1 2008

Keywords

Liquid crystal
Metal-ligand coordination
Supramolecular chemistry
Terdentate

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.05.075

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@article{82864dd7a2f44ba782e777461b36704c,

title = "Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands",

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.",

keywords = "Liquid crystal, Metal-ligand coordination, Supramolecular chemistry, Terdentate",

author = "McKenzie, {Blayne M.} and Miller, {Adriane K.} and Wojtecki, {Rudy J.} and Johnson, {J. Casey} and Burke, {Kelly A.} and Tzeng, {Karis A.} and Mather, {Patrick T.} and Rowan, {Stuart J.}",

note = "Funding Information: This material is based upon work supported by the National Science Foundation under Grant Nos. CAREER CHE- 0133164, CHE-0704026, CAREER CTS-0093880, a National Science Foundation Graduate Research Fellowship awarded to K.A.B. (DGE-0234629), and the Case Western Reserve University President's Research Initiative. The authors are grateful to Dr. J. Benjamin Beck for helpful discussions.",

year = "2008",

month = sep,

day = "1",

doi = "10.1016/j.tet.2008.05.075",

language = "English (US)",

volume = "64",

pages = "8488--8495",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "36",

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TY - JOUR

T1 - Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands

AU - McKenzie, Blayne M.

AU - Miller, Adriane K.

AU - Wojtecki, Rudy J.

AU - Johnson, J. Casey

AU - Burke, Kelly A.

AU - Tzeng, Karis A.

AU - Mather, Patrick T.

AU - Rowan, Stuart J.

N1 - Funding Information: This material is based upon work supported by the National Science Foundation under Grant Nos. CAREER CHE- 0133164, CHE-0704026, CAREER CTS-0093880, a National Science Foundation Graduate Research Fellowship awarded to K.A.B. (DGE-0234629), and the Case Western Reserve University President's Research Initiative. The authors are grateful to Dr. J. Benjamin Beck for helpful discussions.

PY - 2008/9/1

Y1 - 2008/9/1

N2 - 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.

AB - 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.

KW - Liquid crystal

KW - Metal-ligand coordination

KW - Supramolecular chemistry

KW - Terdentate

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U2 - 10.1016/j.tet.2008.05.075

DO - 10.1016/j.tet.2008.05.075

M3 - Article

AN - SCOPUS:47949088505

SN - 0040-4020

VL - 64

SP - 8488

EP - 8495

JO - Tetrahedron

JF - Tetrahedron

IS - 36

ER -

Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands

Abstract

Keywords

ASJC Scopus subject areas

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