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- Title
Reversible Dimerization and Polymerization of a Janus Diradical To Produce Labile C−C Bonds and Large Chromic Effects.
- Authors
Zafra, José L.; Qiu, Lili; Yanai, Naoyuki; Mori, Takamichi; Nakano, Masahiro; Alvarez, Miriam Peña; Navarrete, Juan T. López; Gómez ‐ García, Carlos J.; Kertesz, Miklos; Takimiya, Kazuo; Casado, Juan
- Abstract
Conducting polymers can be synthesized by irreversible diradical monomer polymerization. A reversible version of this reaction consisting of the formation/dissociation of σ-dimers and σ-polymers from a stable quinonoidal diradical precursor is described. The reaction reversibility is made by a quinonoidal molecule which changes its structure to an aromatic species by forming weak and long intermolecular C−C single bonds. The reaction provokes a giant chromic effect of about 2.5 eV. The two opposite but complementary quinonoidal and aromatic tautomers provide the Janus faces of the reactants and products which produces the observed chromic effect. A reaction mechanism is proposed to explain the variety of final products starting with structurally very similar reactants. These reversible reactions, covering an unusual regime of weak covalent supramolecular bonding, yield products which might be envisaged as novel molecular and polymeric soft matter phases.
- Subjects
CONDUCTING polymers; DIMERIZATION; BIRADICALS; POLYMERIZATION; CHROMIC materials; QUINONE derivatives; TAUTOMERISM; CARBON-carbon bonds
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 47, p14783
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201605997