Electroactive chiral oligo- and polymer layers for electrochemical enantiorecognition

Serena Arnaboldi,Sara Grecchi,Patrizia Mussini,Mirko Magni

doi:10.1016/j.coelec.2018.01.001

Serena Arnaboldi, Sara Grecchi + Show 2 more

Open Access

https://doi.org/10.1016/j.coelec.2018.01.001

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Journal: Current Opinion in Electrochemistry	Publication Date: Jan 1, 2018
Citations: 35	License type: cc-by

Affiliation: University of Milan

Abstract

Electronically conducting polymer (ECP) and oligomer films are one of the most popular classes of artificial materials for electrode surface modification and nanostructured electroactive film preparation for use as active layers in advanced sensing electrochemical devices. They can act as both receptors and transducers on account of their electroactivity and easy derivatization in a virtually unlimited structure range, and typically have low cost and easy processability. The tailoring possibilities of ECP films also make them attractive selector candidates to achieve the superior level of molecular recognition represented by enantioselective electroanalysis, implying to discriminate between specular images of a chiral molecule. This superior recognition level requires to endow them with chirality and to employ them as enantiopure films, which can be made along different strategies, with different implications in terms of enantioselectivity, kind of transduction of the recognition event, specificity vs general applicability, preparation difficulty, robustness, etc. In this context an outstanding tool is provided by the “inherent chirality” strategy.

Highlights

Conducting polymers (ECPs) as well as oligomers are one of the most popular classes of artificial materials for electrode surface modification and nanostructured electroactive film preparation for use as active✩ Dedicated to Professor Francesco Sannicolò, an artist in designing intelligent molecules.Current Opinion in Electrochemistry 2018, 7:188–199 layers in advanced sensing devices, their study being prompted by molecular electronics [1,2,3,4,5]
The tailoring possibilities of Electronically conducting polymer (ECP) films make them attractive selector candidates to achieve the superior level of molecular recognition represented by enantioselective electroanalysis, implying to discriminate between specular images of a chiral molecule
This superior recognition level requires to endow them with chirality and to employ them as enantiopure films, which can be made along different strategies, with different implications in terms of enantioselectivity, kind of transduction of the recognition event, specificity vs general applicability, preparation difficulty, robustness, etc

Summary

Introduction

Conducting polymers (ECPs) as well as oligomers are one of the most popular classes of artificial materials for electrode surface modification and nanostructured electroactive film preparation for use as active. Sannicolò’s definition [82,83, SI.1], originating from the same element responsible for the key functional property, here electroactivity) on account of the presence of atropisomeric (i.e., with hindered rotation) or helicoidal elements in the main conjugated backbone, resulting in a regular torsion with an energy barrier far too high to be overcome in the working operating conditions Such approach to electroactive oligomers and polymers of “robust” chirality had been already exploited, e.g., with binaphthyl elements [18] (very popular in chiral catalysis), or helical elements [19], often with conjugation partially impaired by ring connectivity, but hardly for application to electrochemical enantiodiscrimination. Quite recently an additional confirmation came with the outstanding enantioselection observed working on achiral electrodes in inherently chiral media [96]

Conclusion

13. Musiani M

20. MacDiarmid AG

69. Trojanowicz M