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New multiresponsive chromic soft materials: dynamic interconversion of short 2,7-dicyanomethylenecarbazole-based biradicaloid and the corresponding cyclophane tetramer

Wang, D., Capel Ferrón, C., Li, J., Gámez-Valenzuela, S., Ponce Ortiz, R., López Navarrete, J. T., Hernández Jolín, V., Yang, X., Peña Álvarez, M., García Baonza, V., Hartl, F. ORCID: https://orcid.org/0000-0002-7013-5360, Ruiz Delgado, M. C. and Li, H. (2017) New multiresponsive chromic soft materials: dynamic interconversion of short 2,7-dicyanomethylenecarbazole-based biradicaloid and the corresponding cyclophane tetramer. Chemistry- A European Journal, 23 (55). pp. 13776-13783. ISSN 1521-3765

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To link to this item DOI: 10.1002/chem.201702659

Abstract/Summary

This work reports on a quinodimethane-type molecule, 2,7-dicyanomethylene-9-(2-ethylhexyl)carbazole (1), one of the shortest π-conjugated biradicaloids reported to be stable in solution under ambient conditions. This carbazole-based quinoidal precursor is able to form a macrocyclic σ-bonded tetramer (2). The resolved single-crystal X-ray structure of tetramer 2 shows that four molecules of 1 are linked together through four long (CN)2C−C(CN)2 bonds (1.631 Å) resulting from coupling of the unpaired electrons in biradicaloid 1. Dynamic interconversion between monomer 1 and cyclophane tetramer 2 is achieved by reversible cleavage and recovery of the four (CN)2C−C(CN)2 bonds upon soft external stimuli (light absorption, temperature and pressure), which is accompanied by significant color changes. These novel photo-, thermo-, and mechanochromic properties expand the versatility of π-conjugated biradicaloid compounds as novel functional materials that, in combination with spin chemistry and dynamic covalent chemistry, can be relevant in molecular machines, sensors, and switches.

Item Type:Article
Refereed:Yes
Divisions:Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:72388
Uncontrolled Keywords:General Chemistry
Publisher:Wiley

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