Influence of isomeric phthaloperinone monomers on the formation of π-dimers and σ-bonded segments in electrochemically-crosslinked products
| Autor: | Patryk Janasik, Pawel Zassowski, Radoslaw Motyka, Mieczyslaw Lapkowski, Aleksandra Wolińska-Grabczyk, Malgorzata Czichy, Eugenia Grabiec |
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| Rok vydání: | 2021 |
| Předmět: |
Phthalic anhydride
Addition reaction Hydrogen bond General Chemical Engineering Protonation 02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Monomer Deprotonation chemistry Radical ion Polymer chemistry Electrochemistry Structural isomer 0210 nano-technology |
| Zdroj: | Electrochimica Acta. 370:137669 |
| ISSN: | 0013-4686 |
| DOI: | 10.1016/j.electacta.2020.137669 |
| Popis: | A mixture of three constitutional isomers containing terminal reactive phthaloperinone units was obtained by the condensation of 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic anhydride) with 1,8-naphthalenediamine. Both terminal units underwent an addition reaction via electrochemical oxidation and subsequent reduction at the perimidine core and isoindolinone, respectively, to create a multi-directional crosslinked product. The course of electropolymerization depended significantly on the isomer used, which was related to the intermediate products formed during electrooxidation: π-dimers formed in the precursor solution with stronger π-π interactions between radical cations and/or products containing π-conjugated segments: bis-isoindolinone, bis-perimidine (bonded via 3/4 and 3′/4′ positions) and protonated σ-bonded bis-perimidine via 1/6 and 1′/3′/4′/6′ positions, where hydrogen bonds stabilized these latter adducts and prevented their deprotonation. The polymers were characterized by a mixed structure, which had different effects on the long-range interactions, stability of hydrogen bonds providing a redox center located on the protonated dicationic bis-perimidine segment underwent reversible reduction to stable radical cation. |
| Databáze: | OpenAIRE |
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