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Synthesis, chiroptical properties, and self-assembled nanoparticles of chiral conjugated polymers based on optically stable helical aromatic esters.

ABSTRACT: By Suzuki coupling reaction, three pairs of chiral conjugated polymers with optically stable helical aromatic ester subunits as the main-chain were designed and synthesized. Polymers (+)-P-P1 and (-)-M-P1, (+)-P-P2 and (-)-M-P2 showed strong fluorescence emission, strong mirror image CD and circularly polarized luminescence (CPL) signals in THF. For polymers (+)-P-P3 and (-)-M-P3, containing the tetraphenylethene (TPE) moiety, they not only showed obvious aggregation induced enhancement emission (AIEE), but also exhibited mirror image CD signals and aggregation-induced enhancement CPL signals in THF-water mixtures. Moreover, (+)-P-P3 and (-)-M-P3 could also form chiral nanoparticles by solvent evaporation induced self-assembly. Interestingly, it was further found that the size of the nanoparticles could be controlled by the changing of THF/water ratio, and their CPL properties were also shown.

SUBMITTER: Zhang C

PROVIDER: S-EPMC9076947 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Synthesis, chiroptical properties, and self-assembled nanoparticles of chiral conjugated polymers based on optically stable helical aromatic esters.

Zhang Chao C Li Meng M Lu Hai-Yan HY Chen Chuan-Feng CF

RSC advances 20180103 2

By Suzuki coupling reaction, three pairs of chiral conjugated polymers with optically stable helical aromatic ester subunits as the main-chain were designed and synthesized. Polymers (+)-P-P1 and (-)-M-P1, (+)-P-P2 and (-)-M-P2 showed strong fluorescence emission, strong mirror image CD and circularly polarized luminescence (CPL) signals in THF. For polymers (+)-P-P3 and (-)-M-P3, containing the tetraphenylethene (TPE) moiety, they not only showed obvious aggregation induced enhancement emission ...[more]

PMID: 35538983

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Project description:Understanding the solution-state aggregate structure and the consequent hierarchical assembly of conjugated polymers is crucial for controlling multiscale morphologies during solid thin-film deposition and the resultant electronic properties. However, it remains challenging to comprehend detailed solution aggregate structures of conjugated polymers, let alone their chiral assembly due to the complex aggregation behavior. Herein, we present solution-state aggregate structures and their impact on hierarchical chiral helical assembly using an achiral diketopyrrolopyrrole-quaterthiophene (DPP-T4) copolymer and its two close structural analogues wherein the bithiophene is functionalized with methyl groups (DPP-T2M2) or fluorine atoms (DPP-T2F2). Combining in-depth small-angle X-ray scattering analysis with various microscopic solution imaging techniques, we find distinct aggregate in each DPP solution: (i) semicrystalline 1D fiber aggregates of DPP-T2F2 with a strongly bound internal structure, (ii) semicrystalline 1D fiber aggregates of DPP-T2M2 with a weakly bound internal structure, and (iii) highly crystalline 2D sheet aggregates of DPP-T4. These nanoscopic aggregates develop into lyotropic chiral helical liquid crystal (LC) mesophases at high solution concentrations. Intriguingly, the dimensionality of solution aggregates largely modulates hierarchical chiral helical pitches across nanoscopic to micrometer scales, with the more rigid 2D sheet aggregate of DPP-T4 creating much larger pitch length than the more flexible 1D fiber aggregates. Combining relatively small helical pitch with long-range order, the striped twist-bent mesophase of DPP-T2F2 composed of highly ordered, more rigid 1D fiber aggregate exhibits an anisotropic dissymmetry factor (g-factor) as high as 0.09. This study can be a prominent addition to our knowledge on a solution-state hierarchical assembly of conjugated polymers and, in particular, chiral helical assembly of achiral organic semiconductors that can catalyze an emerging field of chiral (opto)electronics.

Dataset Information

Synthesis, chiroptical properties, and self-assembled nanoparticles of chiral conjugated polymers based on optically stable helical aromatic esters.

Publications

Synthesis, chiroptical properties, and self-assembled nanoparticles of chiral conjugated polymers based on optically stable helical aromatic esters.

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