Chiroptical
Inversion Induced by Rotation of a Carbon–Carbon Single Bond:
An Experimental and Theoretical Study
Wei Lu
Ganhong Du
Keyuan Liu
Liming Jiang
Jun Ling
Zhiquan Shen
10.1021/jp410370q.s001
https://acs.figshare.com/articles/journal_contribution/Chiroptical_Inversion_Induced_by_Rotation_of_a_Carbon_Carbon_Single_Bond_An_Experimental_and_Theoretical_Study/2333773
We propose a new
strategy to construct chiral molecular switches with highly reversible
and sensitive chiroptical responses to variations in the external
environment. Its fundamental concept involves a stimuli-triggered
exchange of two conformations presenting significantly different chiroptical
properties through the rotation of a carbon–carbon single bond,
as demonstrated by chiral Schiff bases <i>s</i>-<b>1</b>, <i>s</i>-<b>2</b>, and a salicylamide analogue <i>s</i>-<b>3</b>. Upon addition of base in solution, the
circular dichroism (CD) spectra of these molecular switches displayed
unique changes featuring an inversion of the Cotton effect’s
signs, and the original CD profiles can be recoverd by acidification.
Various spectroscopic studies as well as the conformational analysis
combining with TDDFT computations allowed clear elucidation of the
chiroptical inversion mechanism. It is expected that this kind of
chiroptical switches is of great interest for molecular recognition,
chemosensing, and the construction of molecular-scale devices. Furthermore,
the present study indicates that the use of the conformational transition
about a single bond may serve as the basis for designing chiroptical
inversion systems.
2014-01-09 00:00:00
chiroptical inversion mechanism
chiroptical properties
Various spectroscopic studies
CD profiles
chiroptical responses
salicylamide analogue
Theoretical StudyWe
chiral Schiff bases
chiroptical switches
TDDFT computations
chiroptical inversion systems
Chiroptical Inversion Induced
bond