{"title":"“Click”able monomer and polymers based on Azide-functionalized 3,4-Propylenedioxythiophene with tunable processibility","authors":"Junmo Kang , Kyukwan Zong , Youn-Sik Lee","doi":"10.1016/j.reactfunctpolym.2024.106063","DOIUrl":null,"url":null,"abstract":"<div><div>This research introduces 3,3-bis(azidomethyl)-3,4-dihydro-2<em>H</em>-thieno[3,4-<em>b</em>][1,4]dioxepine (ProDOT-AM2) as a versatile building block monomer for the synthesis of variously functionalized monomers and copolymers via “click”able 1,3-dipolar cycloaddition. The efficiency of this building block as a precursor to a wide range of ProDOT-based monomers is demonstrated by click reaction with various alkynes. The 1,3-dipolar cycloaddition of ProDOT-AM2 with different alkynes in the presence of a catalyst yields a novel class of ProDOT derivatives via a “triazole-locker” mechanism. Depending on the bases utilized, two distinct types of functionalized monomers, namely bistriazole and triazole, are obtained. The resulting polymers from the oxidative polymerization of selected monomers exhibit high solution processability and stability under multiple chemical redox processes, demonstrating potential applications in chemical chromics. Additionally, a conjugated copolymer containing ProDOT-AM2 is synthesized via Stille reaction conditions and subsequently post-functionalized with alkynes via a “triazole-locker” mechanism. Characterization studies via IR and <sup>1</sup>H NMR confirm the successful post-functionalization of the polymer. Electropolymerization of ProDOT-AM2 yields an electroactive polymer (PProDOT-AM2), indicating its potential utility in conducting polymers to be further post-functionalized. Overall, this methodology presents a straightforward approach for synthesizing a new class of monomers for conducting polymers and polymer modification using click chemistry.</div></div>","PeriodicalId":20916,"journal":{"name":"Reactive & Functional Polymers","volume":"205 ","pages":"Article 106063"},"PeriodicalIF":4.5000,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Reactive & Functional Polymers","FirstCategoryId":"5","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1381514824002384","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
This research introduces 3,3-bis(azidomethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (ProDOT-AM2) as a versatile building block monomer for the synthesis of variously functionalized monomers and copolymers via “click”able 1,3-dipolar cycloaddition. The efficiency of this building block as a precursor to a wide range of ProDOT-based monomers is demonstrated by click reaction with various alkynes. The 1,3-dipolar cycloaddition of ProDOT-AM2 with different alkynes in the presence of a catalyst yields a novel class of ProDOT derivatives via a “triazole-locker” mechanism. Depending on the bases utilized, two distinct types of functionalized monomers, namely bistriazole and triazole, are obtained. The resulting polymers from the oxidative polymerization of selected monomers exhibit high solution processability and stability under multiple chemical redox processes, demonstrating potential applications in chemical chromics. Additionally, a conjugated copolymer containing ProDOT-AM2 is synthesized via Stille reaction conditions and subsequently post-functionalized with alkynes via a “triazole-locker” mechanism. Characterization studies via IR and 1H NMR confirm the successful post-functionalization of the polymer. Electropolymerization of ProDOT-AM2 yields an electroactive polymer (PProDOT-AM2), indicating its potential utility in conducting polymers to be further post-functionalized. Overall, this methodology presents a straightforward approach for synthesizing a new class of monomers for conducting polymers and polymer modification using click chemistry.
期刊介绍:
Reactive & Functional Polymers provides a forum to disseminate original ideas, concepts and developments in the science and technology of polymers with functional groups, which impart specific chemical reactivity or physical, chemical, structural, biological, and pharmacological functionality. The scope covers organic polymers, acting for instance as reagents, catalysts, templates, ion-exchangers, selective sorbents, chelating or antimicrobial agents, drug carriers, sensors, membranes, and hydrogels. This also includes reactive cross-linkable prepolymers and high-performance thermosetting polymers, natural or degradable polymers, conducting polymers, and porous polymers.
Original research articles must contain thorough molecular and material characterization data on synthesis of the above polymers in combination with their applications. Applications include but are not limited to catalysis, water or effluent treatment, separations and recovery, electronics and information storage, energy conversion, encapsulation, or adhesion.