Shaping 1,2,4-Triazolium Fluorinated Ionic Liquid Crystals

Abstract

The synthesis and thermotropic behaviour of some di-alkyloxy-phenyl-1,2,4-triazolium trifluoromethane-sulfonate salts bearing a seven-carbon atom perfluoroalkyl chain on the cation is herein described. The fluorinated salts presenting a 1,2,4-triazole as a core and differing in the length of two alkyloxy chains on the phenyl ring demonstrated a typical liquid crystalline behaviour. The mesomorphic properties of this set of salts were studied by differential scanning calorimetry and polarized optical microscopy. The thermotropic properties are discussed on the grounds of the tuneable structures of the salts. The results showed the existence of a monotropic, columnar, liquid crystalline phase for the salts tested. An increase in the temperature mesophase range and the presence of two enantiotropic mesophases for the sixteen-atom alkyloxy chain salt can be observed by increasing the length of the alkyloxy chain on the phenyl ring.

Molecular dynamics and NMR reveal the coexistence of H-bond-assisted and through-space JFH coupling in fluorinated amino alcohols

“…3,4 However, there is a gap of knowledge on nonconventional intramolecular H-bond interactions that needs to be assessed in order to fully understand the role this kind of interaction plays in the conformational stability and preference of molecules, and also to enhance the conformational design protocols in drug discovery, 5 for example. Furthermore, the rapid ascension of fluorinated molecules in the pharmaceutical field [6][7][8][9][10][11][12][13] highlights the demand for a better under-standing of the effects caused by the insertion of fluorine atom(s) on organic molecules, their stereoelectronic effects and the influence of hydrogen bonding [14][15][16][17][18][19][20][21] on their conformational preference.…”

Facile synthesis of substituted 2-aroylbenzo[b]thiophen-3-ols to form novel triazole hybrids using click chemistry

“…This notion is supported by the fact that a large number of the USA Food and Drug Administration (FDA)-approved drugs contain one or several heterocyclic rings in their structures. 1–3 Therefore, access to a chemical library of small molecules containing one or more “privileged” heterocyclic rings is generally considered a prerequisite for effective drug discovery endeavors. 4,5 Among them, sulfur-containing heterocycles are gaining attention in organic synthesis due to their applications in materials sciences, pharmaceutical industries, and food chemistry.…”

Aza‐Heterocyclic Building Blocks with In‐Ring CF2‐Fragment

“…All those achievements in organofluorine chemistry strongly impacted the pharmaceutical industry, giving rise to extraordinary percentages of fluoro‐pharmaceuticals among the total number of FDA‐approved synthetic drugs within a range of 30–44 % over 2016–2021 period [8] . Remarkably, a comprehensive analysis of chemotypes of fluoro‐pharmaceuticals illustrated unbalanced distribution with overwhelming domination of (Het)ArC sp2 −F family of drugs over C sp3 −F counterparts [9,10] .…”