Extraordinary electrochemical stability and extended polaron delocalization of ladder-type polyaniline-analogous polymers

Ji, Xiaozhou; Leng, Mingwan; Xie, Haomiao; Wang, Chenxu; Dunbar, Kim R.; Zou, Yang; Fang, Lei

doi:10.1039/d0sc03348k

Cited by 44 publications

(29 citation statements)

References 58 publications

(66 reference statements)

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“…86 An alternating quinoidal-aromatic constitution can also be achieved by post-polymerization modification of a fully aromatic precursor. For example, Fang's group designed 87 a series of cyclohexadiene-1,4-diimine-derived, quinoidal-aromatic alternating copolymers featuring a ladder-type constitution (Fig. 7).…”

Section: Polymer Chemistry Reviewmentioning

confidence: 99%

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Quinoidal conjugated polymers with open-shell character

Fang

2021

Polym. Chem.

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Section: Polymer Chemistry Reviewmentioning

confidence: 99%

“…14b). 87 The radical cations are delocalized along the ladder-type backbone with extended conjugation. P13c-H possesses dominant Pauli paramagnetism and negligible Curie spin character in the solid state (Fig.…”

Section: Delocalization Of Polarons/bipolaronsmentioning

confidence: 99%

Quinoidal conjugated polymers with open-shell character

Fang

2021

Polym. Chem.

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“…[13] Recently, Fang et al developed several ladder-type polyaniline-analogous polymers using this condensation, which exhibited excellent electrochemical properties. [14] The reaction mechanism is shown in Scheme 2 a, which is similar to imine condensation. [15] This condensation is reversible, and thus is beneficial for COF synthesis.…”

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confidence: 95%

Arylamine‐Linked 2D Covalent Organic Frameworks for Efficient Pseudocapacitive Energy Storage

et al. 2021

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The development of new linkages is one of the most efficient strategies to enrich the diversity of covalent organic frameworks (COFs). Particularly, functional linkages can endow COFs with additional tailored properties besides the building units, which further diversify COFs with desirable functions. Herein, we have developed a new arylamine linkage for the construction of COFs. Two new arylamine‐linked COFs (AAm‐TPB and AAm‐Py) were prepared by condensing cost‐effective dimethyl succinyl succinate (DMSS) with corresponding multitopic amines (TPB‐NH2 and Py‐NH2). Due to the abundant electroactive diphenylamine moieties in the COF skeletons resembling that of polyaniline (PANI), a state‐of‐the‐art conductive polymer, the pseudocapacitive energy storage performance of AAm‐TPB was further investigated. Remarkably, the AAm‐TPB electrode exhibits a high capacitance of 271 F g−1 with a three‐electrode setup at a discharge rate of 1 A g−1, which represents one of the highest capacitances among the reported COF‐based electrode materials.

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“…[26] To highlight these similarities, Fang and co-workers recently reported the synthesis of ladder-type polyaniline analogues, resulting in materials with very similar dye spectroscopy and properties to genipin-amine dyes (reversible oxidation from red to blue materials, delocalized EPR signals, etc). [27,28] Conclusion: In this study, we were able to show that substituting aliphatic amines for aromatic amines results in the formation of a green dye upon reaction with genipin. It was widely hypothesized that these vibrant dyes are the result of an oxidative polymerization reaction, however, analysis of the pigments made led us to revisit this hypothesis.…”

Section: Revisiting the Origins Of Genipin-derived Dyesmentioning

confidence: 66%

Substituent Effects of Amines on Genipin Dye Formation – Insights into Dye Origins

Jeeva¹,

Caputo

2021

Preprint

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<p>Genipin, a naturally occurring iridoid, represents an interesting class of reactive dyes. This colorless molecule produces brilliant blue dyes in the presence of primary aliphatic amines. The mechanism behind this unique reaction has been suggested to proceed via an oxidative polymerization reaction, albeit few studies have investigated this process. By utilizing aromatic amines, we demonstrate that the dye absorption properties can be redshifted to form green dyes as opposed to the blue that is most associated with aliphatic amines. Characterization of the green material with gel-permeation chromatography, mass spectrometry, and electrochemical experiments suggest an alternate structure of the dye molecules and led us to revisit the mechanism behind this reaction. Generation of dyes from the reaction of genipin and methylamine or various aniline derivatives revealed the complete absence of polymeric material and instead revealed a material that contains an open-shell configuration as determined by EPR spectroscopy. Herein we report the first findings that dyes formed from the reaction of genipin with amines form persistent radicals that are likely responsible for their vibrant colors, as opposed to the previously suggested polymer formation. </p>

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Extraordinary electrochemical stability and extended polaron delocalization of ladder-type polyaniline-analogous polymers

Abstract: Electrochemical stability and states-delocalization critically impact the functions and practical applications of electronically active polymers. Incorporation of ladder-type constitution into these polymers represents a promising strategy to enhance the aforementioned...

Cited by 44 publications

References 58 publications

Quinoidal conjugated polymers with open-shell character

Quinoidal conjugated polymers with open-shell character

Arylamine‐Linked 2D Covalent Organic Frameworks for Efficient Pseudocapacitive Energy Storage

Substituent Effects of Amines on Genipin Dye Formation – Insights into Dye Origins

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