jz6b00179_si_001.pdf (1.53 MB)
Toroidal Interaction and Propeller Chirality of Hexaarylbenzenes. Dynamic Domino Inversion Revealed by Combined Experimental and Theoretical Circular Dichroism Studies
journal contribution
posted on 2016-02-16, 00:00 authored by Tomoyo Kosaka, Yoshihisa Inoue, Tadashi MoriHexaarylbenzenes (HABs) have greatly
attracted much attention due
to their unique propeller-shaped structure and potential application
in materials science, such as liquid crystals, molecular capsules/rotors,
redox materials, nonlinear optical materials, as well as molecular
wires. Less attention has however been paid to their propeller chirality.
By introducing small point-chiral group(s) at the periphery of HABs,
propeller chirality was effectively induced, provoking strong Cotton
effects in the circular dichroism (CD) spectrum. Temperature and solvent
polarity manipulate the dynamics of propeller inversion in solution.
As such, whizzing toroids become more substantial in polar solvents
and at an elevated temperature, where radial aromatic rings (propeller
blades) prefer orthogonal alignment against the central benzene ring
(C6 core), maximizing toroidal interactions.