Helicity control of π-conjugated foldamers containing d-glucose-based single enantiomeric units as a chiral source

Abstract

We have succeeded in the helicity control of polymer backbones and their circularly polarized luminescence without the need for chirality of an unnatural antipode, l-glucose.

Synthesis of Platinum-Containing Conjugated Polymers Having QuinoxP* and Bipyridine Ligands. Chirality Transfer from the Phosphine Ligand to the Polymer Backbone

“…We believe that the strategy of the present study leads to a new methodology of molecular design of optically active π-conjugated polymers. Polymers consisting of regularly twisted π-conjugated main chain likely adopt a helical conformation, especially when the backbones are fixed with conformation-locking moieties including helicene, triptycene, and d -glucose. , At the moment, there is no evidence for the present polymers to adopt a helical conformation, presumably due to the low molecular weights. We are planning to introduce long alkyl chains to the benzene ring of QuinoxP*.…”

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

“…2. Monomer (a R )- 3 , containing point and axial chirality derived from glucose and biaryl units, respectively, was synthesized from a previously reported 5,5′-dibromobithiophene derivative, (a R )- 1 ,41 through acetal deprotection followed by esterification at the 4- and 6-positions of the glucose unit. The obtained (a R )- 3 was copolymerized with 4 or 5 via Stille coupling in toluene/ N , N -dimethylformamide (4 : 1, v/v) at 110 °C.…”

“…1). 41 The one-handed helix formation of the resulting polythiophene in a molecularly dispersed state, particularly under good solvent conditions, was investigated using both chiroptical analysis under various conditions and an all-atom molecular dynamics (MD) study.…”

Helix Induction and Inversion of Polymeric Foldamer Regulated by the Single Enantiomers

“…The helical conformations in biomacromolecules like nucleic acids and proteins play a key role in various life activities DOI: 10.1002/marc.202200238 of living organisms. [1] Over the two decades, many artificial helical foldamers have been synthesized to mimic biological functions and applications on asymmetric catalysis, [2][3][4][5][6] chiral recognition, [7][8][9] and circularly polarized luminescence, [10][11][12] etc. In particular, these applications are closely related to the helical conformations.…”