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

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-T ) with a static axial chirality in the main c...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-05, Vol.10 (18), p.4890-4895
Main Authors: Ikai, Tomoyuki, Takayama, Kokoro, Wada, Yuya, Minami, Serena, Apiboon, Chanokporn, Shinohara, Ken-Ichi
Format: Article
Language:English
Subjects:
Addition polymerization
Chemical bonds
Chemistry
Chirality
Circular polarization
Computer simulation
Copolymerization
Coupling (molecular)
Dichroism
Dimers
Hydrogen bonding
Molecular dynamics
Optical activity
Polythiophene
Solvents
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Summary: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-T ) with a static axial chirality in the main chain was synthesized Stille coupling copolymerization of a glucose-linked chiral 5,5'-dibromobithiophene with 2,5-bis(stannyl)thiophene. Poly-T showed a characteristic circular dichroism and circularly polarized luminescence, which were completely different to those observed for an analogous polymer (poly-Ph ) and the corresponding unimer/dimer model compounds. This chiroptical study, combined with the results of all-atom molecular dynamics simulations, revealed that poly-T can fold into a left-handed helical conformation under good solvent conditions. Partial conformational regulation derived from the fixed -conformation of the chiral bithiophene unit was considered a key factor in producing the one-handed helical polythiophene.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc00342h