Document Type

Article

Publication Date

6-13-2012

Publication Title

Beilstein Journal of Organic Chemistry

Department

Department of Chemistry

Abstract

The pH-activated E/Z isomerization of a series of hydrazone-based systems having different functional groups as part of the rotor (R = COMe, CN, Me, H), was studied. The switching efficiency of these systems was compared to that of a hydrazone-based molecular switch (R = COOEt) whose E/Z isomerization is fully reversible. It was found that the nature of the R group is critical for efficient switching to occur; the R group should be a moderate H-bond acceptor in order to (i) provide enough driving force for the rotor to move upon protonation, and (ii) stabilize the obtained Z configuration, to achieve full conversion.

DOI

10.3762/bjoc.8.98

Original Citation

Su X, Lessing T, Aprahamian I. The importance of the rotor in hydrazone-based molecular switches. Beilstein J Org Chem. 2012;8:872-6. doi: 10.3762/bjoc.8.98. Epub 2012 Jun 13. PMID: 23015836; PMCID: PMC3388876.

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