Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers

Martens, Steven; Holloway, Joshua O.; Prez, Filip Du

doi:10.1002/9783527806096.ch13

Cited by 5 publications

(2 citation statements)

References 242 publications

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“…As highlighted earlier, the modification and regulation of the backbone of polymers are crucial for developing energetic polymers. , In this regard, the concept of sequence-controlled polymers (SCPs) has emerged as an intriguing approach to address this issue. − SCPs offer the potential to control the sequence architecture of the polymers, allowing for a deeper understanding of the relationship between the polymer structure and properties and achieving high functionality of polymers. , Lately, the importance of the sequence structure–property relationship of energetic polymers has been recognized. Zhai et al utilized NMR to investigate the sequence architecture of random copolymer 3,3-bis(azidomethyl)oxetane-tetrahydrofuran (BAMO-THF).…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry for Linker-Free BAMO-Based Energetic Sequence-Controlled Copolymers

Li,

Zheng,

Yin

et al. 2023

ACS Appl. Polym. Mater.

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In the field of energetic materials (EMs), soft chains are copolymerized with energetic polymers to improve flexibility. However, this often makes it difficult to achieve simultaneous optimization of the energy level and flexibility due to the random sequence. In this study, a simple approach is presented to develop energetic sequencecontrolled polymers (ESCPs), alternate copolymers poly(3,3-bis(azidomethyl)oxetaneglycol) (P(BAMO-alt-EG)) and poly(3,3-bis(azidomethyl)oxetane-tetrahydrofuran) (P(BAMO-alt-THF)), through click reactions. This approach provides the potential to design and control mechanical and thermal properties in propellant binders by introducing various segments and regulating the sequence structure. These polymers display excellent thermal stability and demonstrate that regulated shorter segmental length promoted better flexibility and less residual carbon content without compromising the energy level of the propellant. The obtained kinetic parameters prove that P(BAMO-alt-EG) released higher heat and accelerated the thermolysis process compared to P(BAMO-alt-THF). These results demonstrate the potential of highly alternating ESCPs as a potential energetic propellant binder.

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Section: Introductionmentioning

confidence: 99%

Click Chemistry for Linker-Free BAMO-Based Energetic Sequence-Controlled Copolymers

Li,

Zheng,

Yin

et al. 2023

ACS Appl. Polym. Mater.

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“…The idea of opening rings to generate sequenced polymers has been previously explored, , and other notable strategies for introducing sequence into copolymers include: template approaches, , iterative methods, − step-growth assembly of macromonomers, − and multicomponent reactions. − Limitations of existing methodologies include the lack of molecular weight control, the narrow range of acceptable monomers, and/or the inclusion of property-dominating linker groups. In recent years, our group’s efforts have focused on the development of synthetic routes to periodic copolymers. , We have been particularly interested in poly(lactic- co -glycolic acid)s (PLGAs) and other poly(α-hydroxyacid)s with applications in biological engineering .…”

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confidence: 99%

Cis-Selective Metathesis to Enhance the Living Character of Ring-Opening Polymerization: An Approach to Sequenced Copolymers

et al. 2018

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The hydrolytic behavior and physical properties of a polymer are directly related to its constituent monomer sequence, yet the scalable and controllable synthesis of sequenced copolymers remains scarcely realized. To address this need, an enhanced version of entropy-driven ring-opening metathesis polymerization (ED-ROMP) has been developed. An unprecedented level of control is obtained by exploiting the kinetic and thermodynamic differences in the metathesis activity of cis- and trans-olefins embedded in large, unstrained macrocycles. First-order rate kinetics were observed, and polymer molecular weights were found to be proportional to catalyst loading. Computational analysis suggests that incorporation of a cis-olefin into the monomer backbone both introduces a thermodynamic driving force and increases the population of metathesis-active conformers. This approach offers a generally applicable method for enhancing living character in ED-ROMP.

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Automated Synthesis Protocol of Sequence‐Defined Oligo‐Urethane‐Amides Using Thiolactone Chemistry

Holloway

Mertens

Prez

et al. 2018

Macromol. Rapid Commun.

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An automated, iterative protocol for the synthesis of multifunctional, sequence‐defined oligo‐urethane‐amides using thiolactone chemistry is reported. Here, sequenced functionalization of the backbone is easily introduced using commercially available primary amines. The chemistry is carried out on solid phase using different supports for better optimization of the synthetic protocol and in order to demonstrate the versatility of the approach. This technique is very effective for iterative synthesis and solid‐phase chemistry and enables the exploration of full automation of this approach using a robotic peptide synthesizer. As a result, this automated protocol allows for the synthesis of a sequence‐defined nonamer of high purity.

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Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers

Cited by 5 publications

References 242 publications

Click Chemistry for Linker-Free BAMO-Based Energetic Sequence-Controlled Copolymers

Click Chemistry for Linker-Free BAMO-Based Energetic Sequence-Controlled Copolymers

Cis-Selective Metathesis to Enhance the Living Character of Ring-Opening Polymerization: An Approach to Sequenced Copolymers

Automated Synthesis Protocol of Sequence‐Defined Oligo‐Urethane‐Amides Using Thiolactone Chemistry

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