The Suzuki coupling reaction as a post-polymerization modification: a promising protocol for construction of cyclic-brush and more complex polymers

Wang, Yunshu; Zhang, Shuangshuang; Wang, Laibing; Zhang, Wei; Zhou, Nianchen; Zhu, Xiulin

doi:10.1039/c5py00551e

“…These groups each offer a convenient chemical handle for post-synthetic transformations, further contributing to the structural diversity available to these systems. [34][35][36][37][38] Unlike previous reports, in which linear dialdehydes yielded [6+6] macrocycles when condensed with a 1,3,5-triphenylbenzene-based diamine, 31,39 the condensation of linear dialdehydes with DAPP yielded pentagonal [5+5] systems. We attribute this change in macrocycle structure to the shorter C-N bonds that make up the pyridine core of DAPP, relative to the C-C bonds within the benzene ring of the previously studied system.…”

Section: Resultsmentioning

confidence: 71%

Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

Strauss

¹

,

Jia

²

,

Evans

³

et al. 2021

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Macrocycles that assemble into nanotubes exhibit emergent properties stemming from their low dimensionality, structural regularity, and distinct interior environments. Here, we report a versatile strategy to synthesize diverse nanotube structures in a single, efficient reaction by using a conserved building block bearing a pyridine ring. Imine condensation of a 2,4,6-triphenylpyridine-based diamine with various aromatic

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“…These groups each offer a convenient chemical handle for post-synthetic transformations, further contributing to the structural diversity available to these systems. [34][35][36][37][38] Unlike previous reports, in which linear dialdehydes yielded [6+6] macrocycles when condensed with a 1,3,5-triphenylbenzene-based diamine, 31,39 the condensation of linear dialdehydes with DAPP yielded pentagonal [5+5] systems. We attribute this change in macrocycle structure to the shorter C-N bonds that make up the pyridine core of DAPP, relative to the C-C bonds within the benzene ring of the previously studied system.…”

Section: Resultsmentioning

confidence: 71%

Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

Strauss¹,

Jia²,

Evans³

et al. 2021

Preprint

0

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Macrocycles that assemble into nanotubes exhibit emergent properties stemming from their low dimensionality, structural regularity, and distinct interior environments. Here, we report a versatile strategy to synthesize diverse nanotube structures in a single, efficient reaction by using a conserved building block bearing a pyridine ring. Imine condensation of a 2,4,6-triphenylpyridine-based diamine with various aromatic dialdehydes yields chemically distinct pentagonal [5+5], hexagonal [3+3], and diamond-shaped [2+2] macrocycles depending on the substitution pattern of the aromatic dialdehyde monomer. Atomic force microscopy and in solvo X-ray diffraction demonstrate that protonation of the macrocycles under the mild conditions used for their synthesis drives assembly into high-aspect ratio nanotubes. Each of the pyridine-containing nanotube assemblies exhibited measurable proton conductivity by electrochemical impedance spectroscopy, with values as high as 10-3 S m-1 (90% R.H., 25°C) that we attribute to differences in their internal pore sizes. This synthetic strategy represents a general method to access robust nanotube assemblies from a universal pyridine-containing monomer, which will enable systematic investigations of their emergent properties.

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“…Some conventional polymer functionalization techniques include the introduction of directly functional monomers into polymer chains via polymerization 2,3 or functional group grafting via postmodifications. 4,5 However, for the former, the species of functional monomer that can be used for polymerization are limited due to the side reaction problems induced by polar functional groups. 6,7 For the latter, it is necessary to execute modification reactions in solution and even introduce catalysts to obtain target functionalization.…”

Section: ■ Introductionmentioning

confidence: 99%

Introducing Mechanochemistry into Rubber Processing: Green-Functionalized Cross-Linking Network of Butadiene Elastomer

Zhang

¹

,

Han

²

,

Bai

³

et al. 2021

ACS Sustainable Chem. Eng.

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Mechanochemistry has injected new vitality into the chemical synthesis process in the solid state as a new, cleaner synthetic technology. Here, to overcome a series of problems induced by common rubber functionalization techniques, a mechanochemistry method based on one-step construction of the functionalized cross-linking network in rubber processing is proposed. Two commercial epoxidized elastomers, epoxidized butadiene rubber and epoxidized natural rubber, were subjected to roll-shearing force in the presence of dopamine. The contrast swelling phenomenon and the pulsed sonication experiment results of model liquid epoxidized polybutadiene with phenol indicates the dialkyl epoxides in epoxidized polybutadiene have intrinsic mechanical activity in the bulk state, and a cross-linking network containing amine and hydroxyl groups is therefore simultaneously constructed via rubber processing. A combination of mechanochemistry with conventional vulcanization technology enables the joint construction of multiple cross-linking networks containing both covalent cross-linking networks and reversible networks, resulting in epoxidized polybutadiene compounds with improved damping performance and malleability and self-healing properties.

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The Suzuki coupling reaction as a post-polymerization modification: a promising protocol for construction of cyclic-brush and more complex polymers

Abstract: The Suzuki coupling reaction was utilized as a highly efficient post-polymerization modification for modular construction of cyclic-brush polymers and other more complex polymers.

Cited by 25 publications

References 45 publications

Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

Introducing Mechanochemistry into Rubber Processing: Green-Functionalized Cross-Linking Network of Butadiene Elastomer

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