Issue 18, 2019

Synthesis of a one-handed helical polythiophene: a new approach using an axially chiral bithiophene with a fixed syn-conformation

Abstract

We report an optically active polythiophene capable of forming a one-handed helically folded conformation without needing aggregate formation, poor solvent conditions, hydrogen-bonded ion-pair formation or guest addition. The target polythiophene (poly-TR) with a static axial chirality in the main chain was synthesized via Stille coupling copolymerization of a glucose-linked chiral 5,5′-dibromobithiophene with 2,5-bis(stannyl)thiophene. Poly-TR showed a characteristic circular dichroism and circularly polarized luminescence, which were completely different to those observed for an analogous polymer (poly-PhR) and the corresponding unimer/dimer model compounds. This chiroptical study, combined with the results of all-atom molecular dynamics simulations, revealed that poly-TR can fold into a left-handed helical conformation under good solvent conditions. Partial conformational regulation derived from the fixed syn-conformation of the chiral bithiophene unit was considered a key factor in producing the one-handed helical polythiophene.

Graphical abstract: Synthesis of a one-handed helical polythiophene: a new approach using an axially chiral bithiophene with a fixed syn-conformation

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Jan 2019
Accepted
02 Apr 2019
First published
03 Apr 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 4890-4895

Synthesis of a one-handed helical polythiophene: a new approach using an axially chiral bithiophene with a fixed syn-conformation

T. Ikai, K. Takayama, Y. Wada, S. Minami, C. Apiboon and K. Shinohara, Chem. Sci., 2019, 10, 4890 DOI: 10.1039/C9SC00342H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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