Synthesis and Characterization of New Chiral Smectic Four-Ring Esters
Magdalena Urbańska1, Mateusz Gratzke1, Michał Czerwiński1
1Institute of Chemistry, Military University of Technology, ul. Sylwestra Kaliskiego 2, 00-908 Warsaw, Poland.
Molecules (Basel, Switzerland)
|July 13, 2024
Summary
New chiral antiferroelectric liquid crystals (AFLCs) offer enhanced chemical stability and longer helical pitch. These materials improve optical contrast in photonic devices, paving the way for advanced electro-optical applications.
Area of Science:
- Materials Science
- Organic Chemistry
- Condensed Matter Physics
Background:
- Orthoconic antiferroelectric liquid crystals (OAFLCs) are promising for photonic devices due to fast switching and high optical contrast.
- Existing OAFLCs often exhibit poor chemical stability and short helical pitches, limiting their practical use.
Purpose of the Study:
- To synthesize and characterize novel chiral antiferroelectric liquid crystals (AFLCs) with improved chemical stability and structural features.
- To evaluate the potential of these new AFLCs for enhancing the performance of OAFLC mixtures in electro-optical applications.
Main Methods:
- Synthesis of two chiral AFLCs with a four-ring rigid core structure.
- Mesomorphic property analysis using polarizing optical microscopy and differential scanning calorimetry.
- Spectroscopic and electro-optical studies to determine helical pitch, tilt angle, and spontaneous polarization.
Main Results:
- Synthesized compounds exhibit enantiotropic chiral smectic mesophases (SmA*, SmC*, SmCA*) over broad temperature ranges.
- Incorporation of synthesized compounds into antiferroelectric mixtures increased helical pitch and tilt angle.
- Spontaneous polarization remained largely unaffected, maintaining high optical contrast and a near-perfect dark state.
Conclusions:
- The novel chiral AFLCs possess high chemical stability and desirable mesomorphic properties.
- Doping existing mixtures with these compounds enhances key parameters for OAFLC applications.
- The studied materials show significant potential for practical applications in photonic and electro-optical devices.
Related Concept Videos
Stereoisomerism of Cyclic Compounds
8.8K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
8.8K
Chirality at Nitrogen, Phosphorus, and Sulfur
5.7K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
5.7K
Prochirality
3.8K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
3.8K
Molecules with Multiple Chiral Centers
11.5K
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
11.5K
Naming Enantiomers
20.2K
The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
20.2K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
3.4K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.4K


![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)