DFT study of hydrazone-based molecular switches: the effect of different stators on the on/off state distribution

ABSTRACT

Hydrazones are popular building blocks in the development of functional materials because of their simple structure, straightforward synthesis, hydrolytic stability and tunable properties. Although a significant body of experimental information has been accumulated on the hydrazone-based rotary switches, mechanistic studies are still scarce. The effect of different stator units (phenyl-, naphthyl- and quinolinyl) on the on/off state distribution is studied in details at various computational levels in order to select a reliable computational level for a further computational study of the switching mechanism and rotary action of these systems.

GRAPHICAL ABSTRACT

KEYWORDS:

• Molecular switches
• hydrazones
• DFT
• tautomers
• tautomeric forms generation

Disclosure statement

No potential conflict of interest was reported by the authors.

ORCID

Silvia Angelova http://orcid.org/0000-0003-4717-8028

Liudmil Antonov http://orcid.org/0000-0003-0520-1517

Supplemental online material

Ambit–Tautomer generated tautomeric forms for compounds 1–3, calculated relative stabilities (ΔE and ΔG) in the gas phase for compounds 1 and 3, calculated relative stabilities (ΔE and ΔG) in acetonitrile (in kcal mol⁻¹) for compounds 1–3.

Additional information

Funding

The authors acknowledge the financial support from Bulgarian National Science Fund under the project ‘MolRobot’ (DN0910/2016) and the COST Action CM1405 (European Cooperation in Science and Technology) (Molecules in motion, MOLIM) for the ideas and knowledge exchange.