Potential-Driven Chirality Manifestations and Impressive Enantioselectivity by Inherently Chiral Electroactive Organic Films
| Autor: | Tiziana Benincori, Monica Panigati, Francesco Sannicolò, Roberto Cirilli, Giovanna Longhi, Lothar Dunsch, Marco Pierini, Patrizia R. Mussini, Simona Rizzo, V. Bonometti, Serena Arnaboldi, Wlodzimierz Kutner |
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| Rok vydání: | 2014 |
| Předmět: |
Polymers
chirality circular dichroism electrochemistry heterocycles oligomerization Nanotechnology Electrons 010402 general chemistry 01 natural sciences Catalysis Stereocenter Delocalized electron Heterocyclic Compounds Molecular Structure 010405 organic chemistry Chemistry Breathing system Stereoisomerism General Chemistry General Medicine 0104 chemical sciences Electroactive materials Chemical physics Electric potential Chirality (chemistry) Thianaphthene |
| Zdroj: | Angewandte Chemie International Edition |
| ISSN: | 0044-8249 |
| Popis: | The typical design of chiral electroactive materials involves attaching chiral pendants to an electroactive polyconjugated backbone and generally results in modest chirality manifestations. Discussed herein are electroactive chiral poly-heterocycles, 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). As the stereogenic element coincides with the electroactive one, films of impressive chiroptical activity and outstanding enantiodiscrimination properties are obtained. 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. |
| Databáze: | OpenAIRE |
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