Related Experiment Video
Updated: Jul 15, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Unexpected chiroptical inversion observed for supramolecular complexes formed between an achiral polythiophene and
Chun Li1, Munenori Numata, Masayuki Takeuchi
1Department of Chemistry and Biochemistry, Graduated School of Engineering, Kyushu University, Fukuoka 819-0395, Japan.
Abstract:
A series of supramolecular complexes between a water-soluble achiral polythiophene derivative (PT-1) and various nucleotides has been prepared. It was found that upon the introduction of adenosine diphosphate (ADP), adenosine triphosphate (ATP), and uridine triphosphate (UTP) into aqueous solutions of achiral PT-1, which has a random-coiled conformation, chiral supramolecular pi-stacked aggregates of PT-1 can be constructed. These complexes exhibit an unique split-type induced circular dichroism (ICD) in the pi-pi* transition region of the main chain. In particular, it was found that the Cotton effect of the chiral supramolecular PT-1/ATP aggregates reveals a dramatic inversion of chirality with a change in the concentration of ATP, which has not been previously observed in chiral macromolecular complexes. On the basis of extensive investigations performed with UV/Vis spectroscopy, CD spectroscopy, TEM, AFM, and dynamic light scattering (DLS), a possible mechanism for the formation of chiral superstructures of PT-1 and chiroptical inversion induced by changes in ATP concentration is proposed.
Related Concept Videos
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Thermal and Photochemical Electrocyclic Reactions: Overview
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Properties of Enantiomers and Optical Activity
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility

