Liquid Crystalline Order from ortho-Phenylene Ethynylene Macrocycles
- 30 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (29), 9264-9265
- https://doi.org/10.1021/ja060354b
Abstract
Triangular ortho-phenylene ethynylene (o-PE) cyclic trimers represent a novel member of shape-persistent macrocycles. Shape-persistent cyclic structures remain of great interest as molecular components in the fields of supramolecular materials, host-guest chemistry, and materials science. Novel discotic liquid crystalline properties are reported from triangular-shaped o-PE macrocycles containing branched alkoxy- and/or triethylene glycol (TEG) side chains using polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD). The macrocycles self-assemble into thermotropic rectangular columnar (Colr) (for M1), hexagonal columnar (Colh) (for M2), and discotic nematic (for M3) mesophases at room temperature. This work shows clearly that electron-rich PE macrocycles can form LC materials. Alkyl side chains in M1 promote order, while hydrophilic side chains of M2 generate an amphiphilic structure that provides a different driving force for organization. The ability to create ordered self-assembling materials from these novel electron-rich macrocycles is important in nanotechnology.This publication has 20 references indexed in Scilit:
- Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne MetathesisJournal of the American Chemical Society, 2004
- Self-Assembly of C3h and Cs Symmetric Keto-enamine Forms of Tris(N-salicyl-ideneanilines) into Columnar Phases: A New Family of Discotic Liquid CrystalsJournal of the American Chemical Society, 2004
- Supramolecular dendritic liquid quasicrystalsNature, 2004
- Theoretical Study of Helix Formation in Substituted Phenylene Ethynylene OligomersThe Journal of Organic Chemistry, 2003
- Synthesis of Alkoxy-Substituted ortho-Phenylene Ethynylene OligomersOrganic Letters, 2003
- A Facile Synthesis of Large Extraannular-Functionalized Phenyl-Ethynyl Macrocycles Containing m-Terphenyl UnitsOrganic Letters, 2002
- Synthesis and Association Behavior of Butadiyne-Bridged [44](2,6)Pyridinophane and [46](2,6)Pyridinophane DerivativesOrganic Letters, 2000
- Hierarchical Growth of Chiral Self-Assembled Structures in Protic MediaJournal of the American Chemical Society, 2000
- Shape-Persistent Molecular Architectures of Nanoscale DimensionAccounts of Chemical Research, 1997
- Direct electron transfer involving free-solute ferrocene in fluid electrolyte on an oxocuprate (Bi(Pb) 2223) electrode in the superconducting stateJournal of the American Chemical Society, 1992