Copolymers of pyrrole with N-alkynylpyrroles

Yamamoto, Takakazu; Yamagata, Yusuke; Yamashita, Risako; Abla, Mahmut; Fukumoto, Hiroki; Koizumi, Toru

doi:10.1016/j.synthmet.2012.11.021

Cited by 4 publications

(5 citation statements)

References 46 publications

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“…[156][157][158] This can be rationalized by the presence of a p lone pair (pyrrole-type nitrogen in the 1-position, Fig. 6) within the conjugation pathway [159][160][161][162] causing a formal cross conjugation between the triazole's substituents. 163 The lone pair cannot mediate p-electron delocalization leading to consecutive ''single bonds'' at the substituted nitrogen atom.…”

Section: P Conjugationmentioning

confidence: 99%

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Beyond click chemistry – supramolecular interactions of 1,2,3-triazoles

2014

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The research on 1,2,3-triazoles has been lively and ever-growing since its stimulation by the advent of click chemistry. The attractiveness of 1H-1,2,3-triazoles and their derivatives originates from their unique combination of facile accessibility via click chemistry and truly diverse supramolecular interactions, which enabled myriads of applications in supramolecular and coordination chemistry. The nitrogen-rich triazole features a highly polarized carbon atom allowing the complexation of anions by hydrogen and halogen bonding or, in the case of the triazolium salts, via charge-assisted hydrogen and halogen bonds. On the other hand, the triazole offers several N-coordination modes including coordination via anionic and cationic nitrogen donors of triazolate and triazolium ions, respectively. After CH-deprotonation of the triazole and the triazolium, powerful carbanionic and mesoionic carbene donors, respectively, are available. The latter coordination mode even features non-innocent ligand behavior. Moreover, these supramolecular interactions can be combined, e.g., in ion-pair recognition, preorganization by intramolecular hydrogen bond donation and acceptance, and in bimetallic complexes. Ultimately, by clicking two building blocks into place, the triazole emerges as a most versatile functional unit allowing very successful applications, e.g., in anion recognition, catalysis, and photochemistry, thus going far beyond the original purpose of click chemistry. It is the intention of this review to provide a detailed analysis of the various supramolecular interactions of triazoles in comparison to established functional units, which may serve as guidelines for further applications.

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Section: P Conjugationmentioning

confidence: 99%

“…163 The lone pair cannot mediate p-electron delocalization leading to consecutive ''single bonds'' at the substituted nitrogen atom. [159][160][161] Similarly, the nitrogen lone pair in polyanilines acts as an insulator in the electronic ground state. This effect may be visualized using potential contributing structures (Fig.…”

Section: P Conjugationmentioning

confidence: 99%

Beyond click chemistry – supramolecular interactions of 1,2,3-triazoles

2014

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“…Electrochemical copolymerisation of Py and either 6 or 7 produces copolymer films with lower conductivity than pure PPy; however, the incorporation of 2-phenylethynyl groups originating from eight into the copolymer chain considerably enhances its thermal stability [ 26 ]. Moreover, the presence of triple bonds allows the copolymers to be subjected to photo-crosslinking.…”

Section: Copolymerisation Of Pyrrolementioning

confidence: 99%

Electrochemically Produced Copolymers of Pyrrole and Its Derivatives: A Plentitude of Material Properties Using “Simple” Heterocyclic Co-Monomers

Jarosz¹,

Ledwon²

2021

Materials

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Polypyrrole is a classical, well-known conjugated polymer that is produced from a simple heterocyclic system. Numerous pyrrole derivatives exhibit biological activity, and the repeat unit is a common building block present in the chemical structure of many polymeric materials, finding wide application, primarily in optoelectronics and sensing. In this work, we focus on the variety of copolymers and their material properties that can be produced electrochemically, even though all these systems are obtained from mixtures of the “simple” pyrrole monomer and its derivatives with different conjugated and non-conjugated species.

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“…Additionally, polymerizations in which the alkyne remains intact have been reported. Yamamoto published the co-polymerization of N -alkynyl pyrroles 304a,b with the di(stanyl)thiophenes 305a,b (Scheme 80, Reaction (3) [128,129,130]). Yamamoto also reported the oxidative polymerization of 307 with TBAPF 6 in 2012 (Scheme 80, Reaction (4) [131]).…”

Section: Applications Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis.

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Copolymers of pyrrole with N-alkynylpyrroles

Cited by 4 publications

References 46 publications

Beyond click chemistry – supramolecular interactions of 1,2,3-triazoles

Beyond click chemistry – supramolecular interactions of 1,2,3-triazoles

Electrochemically Produced Copolymers of Pyrrole and Its Derivatives: A Plentitude of Material Properties Using “Simple” Heterocyclic Co-Monomers

Preparation and Utility of N-Alkynyl Azoles in Synthesis

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