The synthesis of novel 3-substituted pyrrole monomers possessing chiral side groups: a study of their chemical polymerisation and the assessment of their chiral discrimination properties

Conducting polymers in chemical sensors and arrays

“…However, an adsorption of long chain aliphatic alcohols leads to higher film resistances, in this case a prevailing effect of these non-polar compounds is their insulating properties hindering charge transfer between polymer chains [76,108]. Chiral gases can be detected by CP modified by chiral side groups [110]. The major drawback of CP gas sensors is their poor selectivity and strong interference with humidity.…”

Potential‐Driven Chirality Manifestations and Impressive Enantioselectivity by Inherently Chiral Electroactive Organic Films

“…Such deformations, revealed by CD spectroelectrochemistry, are elastic and reversible, thus suggesting a breathing system.The combination of chirality with electrical conductivity endows organic polyconjugated materials with a variety of attractive features: [1] 1) the ordered spontaneous chain assembly induced by chirality; [2] 2) non-centrosymmetry, a prerequisite for second-order NLO applications; [3,4] 3) the ability to discriminate between enantiomers, which is required in chemical sensors designed for the detection of chiral analytes; [5][6][7] 4) the ability to act as chiral electrode surfaces for asymmetric redox reactions. Discussed herein are electroactive chiral polyheterocycles, where chirality is not external to the electroactive backbone but inherent to it, and results from a torsion generated by the periodic presence of atropisomeric, conjugatively active biheteroaromatic scaffolds, (3,3'-bithianaphthene).…”

“…Moreover, chirality manifestations can be finely and reversibly tuned by the electric potential, as progressive injection of holes forces the two thianaphthene rings to co-planarize to favor delocalization. Such deformations, revealed by CD spectroelectrochemistry, are elastic and reversible, thus suggesting a breathing system.The combination of chirality with electrical conductivity endows organic polyconjugated materials with a variety of attractive features: [1] 1) the ordered spontaneous chain assembly induced by chirality; [2] 2) non-centrosymmetry, a prerequisite for second-order NLO applications; [3,4] 3) the ability to discriminate between enantiomers, which is required in chemical sensors designed for the detection of chiral analytes; [5][6][7] 4) the ability to act as chiral electrode surfaces for asymmetric redox reactions. [8] Chirality is usually introduced into the materials by attaching chiral pendants to the electroactive conjugated backbone through suitable linkers [1] and many different chiral substituents have been either chosen from the chiral pool, such as sugars and amino acids, or manmade for dedicated applications.…”

Synthesis and polymerization studies of 3-(+) and (−)-menthyl carboxylate pyrroles

“…Research that followed included the synthesis of new chiral monomers with a variety of chiral substituents attached to the 3-position, or the N-position, of pyrrole [2][3][4][5][6][7][8].…”

“…Previous publications reporting the addition of chiral groups to the 3-position of pyrrole generally involved a lengthy series of synthetic steps, such as the synthesis of S-(-) and R-(+)-3-pyrrol ethanoic acid menthol esters ( Fig. 1) which was achieved by De Lacy Costello in five high yielding steps [2].…”