Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals

Synthesis and characterization

Mahabaleshwara Subrao, Dakshina Murthy Potukuchi, Girish Sharada Ramachandra, Poornima Bhagavath, Sangeetha G. Bhat, Srinivasulu Maddasani

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Two novel series of unsymmetrically substituted 1,2,4-oxadiazole viz., R.Ox.C∗Cn compounds are synthesized and characterized. An optically active, (S)-(+)-methyl 3-hydroxy-2-methylpropionate is used to introduce a chiral center in the molecule. A biphenyl moiety prepared by Suzuki coupling reaction is directly attached to the oxadiazole core at C-5 position. Investigations for the phase behavior revealed that the series with a benzyl group on one end of the oxadiazole core exhibits an 1D orthogonal smectic-A phase while the second series with dodecyl flexible end chain shows orthogonal smectic-A and tilted chiral smectic-C (SmC∗) phases over a wide range of temperatures. The smectic-C phase exhibits ferroelectric (FE) polarization switching. The mesomorphic thermal stabilities of these compounds are discussed in the domain of the symmetry and the flexibility of the alkyloxy end chain length attached to the chiral center.

Original languageEnglish
Pages (from-to)233-241
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume11
DOIs
Publication statusPublished - 11-02-2015

Fingerprint

Oxadiazoles
Liquid Crystals
Ferroelectric materials
Phase behavior
Chain length
Thermodynamic stability
Polarization
Molecules
diphenyl
Temperature

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

@article{abe2797d81474b6e83fa84f79c911ace,
title = "Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals: Synthesis and characterization",
abstract = "Two novel series of unsymmetrically substituted 1,2,4-oxadiazole viz., R.Ox.C∗Cn compounds are synthesized and characterized. An optically active, (S)-(+)-methyl 3-hydroxy-2-methylpropionate is used to introduce a chiral center in the molecule. A biphenyl moiety prepared by Suzuki coupling reaction is directly attached to the oxadiazole core at C-5 position. Investigations for the phase behavior revealed that the series with a benzyl group on one end of the oxadiazole core exhibits an 1D orthogonal smectic-A phase while the second series with dodecyl flexible end chain shows orthogonal smectic-A and tilted chiral smectic-C (SmC∗) phases over a wide range of temperatures. The smectic-C phase exhibits ferroelectric (FE) polarization switching. The mesomorphic thermal stabilities of these compounds are discussed in the domain of the symmetry and the flexibility of the alkyloxy end chain length attached to the chiral center.",
author = "Mahabaleshwara Subrao and Potukuchi, {Dakshina Murthy} and Ramachandra, {Girish Sharada} and Poornima Bhagavath and Bhat, {Sangeetha G.} and Srinivasulu Maddasani",
year = "2015",
month = "2",
day = "11",
doi = "10.3762/bjoc.11.26",
language = "English",
volume = "11",
pages = "233--241",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals : Synthesis and characterization. / Subrao, Mahabaleshwara; Potukuchi, Dakshina Murthy; Ramachandra, Girish Sharada; Bhagavath, Poornima; Bhat, Sangeetha G.; Maddasani, Srinivasulu.

In: Beilstein Journal of Organic Chemistry, Vol. 11, 11.02.2015, p. 233-241.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals

T2 - Synthesis and characterization

AU - Subrao, Mahabaleshwara

AU - Potukuchi, Dakshina Murthy

AU - Ramachandra, Girish Sharada

AU - Bhagavath, Poornima

AU - Bhat, Sangeetha G.

AU - Maddasani, Srinivasulu

PY - 2015/2/11

Y1 - 2015/2/11

N2 - Two novel series of unsymmetrically substituted 1,2,4-oxadiazole viz., R.Ox.C∗Cn compounds are synthesized and characterized. An optically active, (S)-(+)-methyl 3-hydroxy-2-methylpropionate is used to introduce a chiral center in the molecule. A biphenyl moiety prepared by Suzuki coupling reaction is directly attached to the oxadiazole core at C-5 position. Investigations for the phase behavior revealed that the series with a benzyl group on one end of the oxadiazole core exhibits an 1D orthogonal smectic-A phase while the second series with dodecyl flexible end chain shows orthogonal smectic-A and tilted chiral smectic-C (SmC∗) phases over a wide range of temperatures. The smectic-C phase exhibits ferroelectric (FE) polarization switching. The mesomorphic thermal stabilities of these compounds are discussed in the domain of the symmetry and the flexibility of the alkyloxy end chain length attached to the chiral center.

AB - Two novel series of unsymmetrically substituted 1,2,4-oxadiazole viz., R.Ox.C∗Cn compounds are synthesized and characterized. An optically active, (S)-(+)-methyl 3-hydroxy-2-methylpropionate is used to introduce a chiral center in the molecule. A biphenyl moiety prepared by Suzuki coupling reaction is directly attached to the oxadiazole core at C-5 position. Investigations for the phase behavior revealed that the series with a benzyl group on one end of the oxadiazole core exhibits an 1D orthogonal smectic-A phase while the second series with dodecyl flexible end chain shows orthogonal smectic-A and tilted chiral smectic-C (SmC∗) phases over a wide range of temperatures. The smectic-C phase exhibits ferroelectric (FE) polarization switching. The mesomorphic thermal stabilities of these compounds are discussed in the domain of the symmetry and the flexibility of the alkyloxy end chain length attached to the chiral center.

UR - http://www.scopus.com/inward/record.url?scp=84923320489&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84923320489&partnerID=8YFLogxK

U2 - 10.3762/bjoc.11.26

DO - 10.3762/bjoc.11.26

M3 - Article

VL - 11

SP - 233

EP - 241

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -