One‐Step Route to Ladder‐Type C–N Linked Conjugated Polymers

Ren, Xiaojie; Zhang, Hailei; Song, Meining; Cheng, Cong; Zhao, Hongchi; Wu, Yonggang

doi:10.1002/macp.201900044

Cited by 9 publications

(5 citation statements)

References 22 publications

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“…The unique multiple-stranded architecture of the conjugated ladder polymer endows material with a constrained chain conformation that results in good conjugation, carrier mobility, and luminescence intensity, so it has been widely investigated in organic light-emitting diodes and the organic field effect . Despite remarkable advances in the past decade, fully conjugated ladder-type macromolecules still remain a major synthetic challenge …”

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confidence: 99%

Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular S_NAr Reaction

et al. 2021

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Symmetric ladder-type oligo(p-aniline)s and poly(p-aniline)s were successfully synthesized by an intramolecular ring closure in a highly efficient SNAr reaction from oligo(p-phenylene)s and poly(p-phenylene)s with fluorine (F) and secondary amine (NH) groups. Unlike Cadogan ring closure, the newly designed cyclization reaction will not produce a mixture of symmetric and nonsymmetric structures. Moreover, the introduction of the F atom does not hinder Suzuki polymerization. The result indicates that preparing regular oligomers and polymers with a nitrogen bridge is possible.

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confidence: 99%

Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular S_NAr Reaction

et al. 2021

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“…Our single‐handed ladder polymers were accessed (Scheme 1) with chirality‐assisted synthesis (CAS), [4aa, 5] which provided us with precise control of the helix geometry (diameter and rise). Please see the Supporting Information for detailed synthetic protocols, as well as a model coupling reaction carried out with tert ‐butyloxycarbonyl (Boc)‐protected ends, which was used to establish the coupling chemistry and proceeded in 92 % yield [13] . Notably, a universal chiral building block 3 , constructed from a shape‐persistent 9,10‐dihydro‐9,10‐ethanoanthracene backbone, can be utilized to create helices with different shapes by simply changing the geometry of the bis(boronic ester) linkage.…”

Section: Figurementioning

confidence: 99%

Helical Molecular Springs with Varying Spring Constants

et al. 2022

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We report a general synthetic route toward helical ladder polymers with varying spring constants, built with chirality-assisted synthesis (CAS). Under tension and compression, these shape-persistent structures do not unfold, but rather stretch and compress akin classical Hookean springs. Our synthesis is adaptable to helices with different pitch and diameter, which allowed us to investigate how molecular flexibility in solution depends on the exact geometry of the ladder polymers. Specifically, we showed with molecular dynamic simulations and by measuring the longitudinal 1 H NMR relaxation times (T 1 ) for our polymers at different Larmor frequencies, that increasing the helix diameter leads to increased flexibility. Our results present initial design rules for tuning the mechanical properties of intrinsically helical ladder polymers in solution, which will help inspire a new class of robust, spring-like molecular materials with varying mechanical properties.

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“…Our group have made some attempts. We once successfully constructed ladder-type C-N-linked conjugated polymers via tandem reaction; specifically, we used the Pd-catalyzed Suzuki coupling/Schiff’s base reaction [ 22 ]. The model compounds are achieved in high yields.…”

Section: Introductionmentioning

confidence: 99%

Tandem Suzuki Polymerization/Heck Cyclization Reaction to Form Ladder-Type 9,9′-Bifluorenylidene-Based Conjugated Polymer

Zhu

Liu

et al. 2023

Polymers

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The synthesis of ladder-type 9,9′-bifluorenylidene-based conjugated polymer is reported. Unlike the typical synthetic strategy, the new designed ladder-type conjugated polymer is achieved via tandem Suzuki polymerization/Heck cyclization reaction in one-pot. In the preparation process, Suzuki polymerization reaction occurred first and then the intramolecular Heck cyclization followed smoothly under the same catalyst Pd(PPh3)4. The model reaction proved that the introduction of iodine (I) for this tandem reaction can effectively control the sequential bond-forming process and inhibit the additional competitive side reactions. Thus, small-molecule model compounds could be obtained in high yields. The successes of the synthesized small molecule and polymer compounds indicate that the Pd-catalyzed tandem reaction may be an effective strategy for improving extended π-conjugated materials.

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One‐Step Route to Ladder‐Type C–N Linked Conjugated Polymers

Cited by 9 publications

References 22 publications

Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular S_NAr Reaction

Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular S_NAr Reaction

Helical Molecular Springs with Varying Spring Constants

Tandem Suzuki Polymerization/Heck Cyclization Reaction to Form Ladder-Type 9,9′-Bifluorenylidene-Based Conjugated Polymer

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One‐Step Route to Ladder‐Type C–N Linked Conjugated Polymers

Cited by 9 publications

References 22 publications

Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular SNAr Reaction

Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular SNAr Reaction

Helical Molecular Springs with Varying Spring Constants

Tandem Suzuki Polymerization/Heck Cyclization Reaction to Form Ladder-Type 9,9′-Bifluorenylidene-Based Conjugated Polymer

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Product

Resources

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Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular S_NAr Reaction

Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular S_NAr Reaction