TY - JOUR
T1 - Photochemical and Electrochemical Triggered Bis(hydrazone) Switch
AU - Gordillo, Mónica A.
AU - Soto-Monsalve, Mónica
AU - Carmona-Vargas, Christian C.
AU - Gutiérrez, Gustavo
AU - D'vries, Richard F.
AU - Lehn, Jean-Marie
AU - Chaur, Manuel N.
PY - 2017/10/20
Y1 - 2017/10/20
N2 - 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.
AB - 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.
KW - bis(hydrazone)
KW - configurational isomers
KW - photoisomerization
KW - supramolecular chemistry
KW - thiopyrimidine
UR - http://www.scopus.com/inward/record.url?scp=85032854885&partnerID=8YFLogxK
UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85032854885&origin=recordpage
U2 - 10.1002/chem.201703065
DO - 10.1002/chem.201703065
M3 - RGC 21 - Publication in refereed journal
SN - 0947-6539
VL - 23
SP - 14872
EP - 14882
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 59
ER -