Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 59, Pages 14872-14882Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201703065
Keywords
bis(hydrazone); configurational isomers; photoisomerization; supramolecular chemistry; thiopyrimidine
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Funding
- Vicerrectoria de Investigaciones
- El Departamento Administrativo de Ciencia, Tecnologia e Innovacion (COLCIENCIAS)
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior from Brazilian Ministry of Education
- Conselho Nacional de Desenvolvimento Cientifico y Tecnologico from Brazilian Ministry of Education
- University of Strasbourg
- Centro de Excelencia en Nuevos Materiales (CENM) from the Universidad del Valle (Colombia)
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Herein, we report the synthesis of a double hydrazone capable of undergoing photochemical E/Z isomerization through the imine double bonds. The bis(hydrazone) 1-E,E can be considered as a two-arm system in which the controlled movement of each arm is obtained by photo-modulation, making possible the appearance of two isolable metastable isomeric states 1-E,Z and 1-Z,Z. Such states are characterized by very specific structural, optical, and electrochemical properties. The latter allows the reversible return from either 1-E,Z or 1-Z,Z to the 1-E,E state. Our results are of great importance in the further development of molecular machines and photochemically controlled reactions by introducing for the first time double hydrazones as tunable photochemical switches.
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