Synthesis of methyl‐substituted azobenzene–carbazole conjugated copolymers with photoinduced structural changes

Otaki, Masashi; Kumai, Reiji; Goto, Hiromasa

doi:10.1002/pola.29445

Cited by 6 publications

(3 citation statements)

References 27 publications

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“…[13,14] Several studies have been reported using the optical behavior of such main chain azobenzene polymers. [15][16][17] Furthermore, main chain-type azobenzene self-assembles into a chiral twodimensional structure by imparting chirality have been reported. [18][19][20][21] Electrochemical polymerization (EP) is one of the polymerization methods for conjugated polymers.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, copolymers of azobenzene and various heterocycles made a clear difference in the optical behavior of the azobenzene backbone [13,14] . Several studies have been reported using the optical behavior of such main chain azobenzene polymers [15–17] . Furthermore, main chain‐type azobenzene self‐assembles into a chiral two‐dimensional structure by imparting chirality have been reported [18–21] …”

Section: Introductionmentioning

confidence: 99%

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Electrochromism of Main‐Chain Polyazobenzenes Synthesized in Liquid Crystal Template and Its Orientation Behavior

Otaki

Goto

2022

ChemistrySelect

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Azobenzene with a controllable structure is suitable for applications in electronic devices due to its multichromatic and optoelectrical properties. Therefore, in this study, main chain‐type conjugated polyazobenzenes are synthesized via electrochemical polymerization (EP) using liquid crystal (LC) as a template. EP in cholesteric liquid crystal (CLC) affords π‐conjugated polyazobezene films with CLC‐like helical morphologies and optical activities due to chirality transfer from CLCs. Further, EP in a macroscopically aligned nematic liquid crystal (NLC) field obtained via a simple rubbing method resulted in macroscopically ordered conjugated polyazobenzene films. Consequently, main chain‐type polyazobenzene films having a controllable structure can be conveniently obtained using LC as a template.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electrochromism of Main‐Chain Polyazobenzenes Synthesized in Liquid Crystal Template and Its Orientation Behavior

Otaki

Goto

2022

ChemistrySelect

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“…Actually, the polymer with azo motifs on the main chain displayed more absorbing physicochemical properties. Moreover, remarkable conjugated polymers containing azo chromophores on the main chain, which possessed photocontrollable higher-order structures, have been extensively reported. − Extending the delocalization degree of π-electrons of azo-based derivatives leads to a distinct red shift of the π → π* transition band. More importantly, these conjugated polymers showed decreased photoswitching efficiency of the azo motif.…”

Section: Introductionmentioning

confidence: 99%

Azobenzene-containing Alternating and Random Metathesis Copolymers toward Gaining More Insight into Photoisomerization Properties

Song

Xiao-tian

et al. 2021

Macromolecules

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Using alternating diene metathesis (ALTMET) polycondensation and acyclic diene metathesis (ADMET) polymerization, two kinds of alternating and random copolymers from electron-deficient azobenzene (azo)-functionalized α,ω-diene monomers that are photoresponsive molecules and comonomers such as electron-rich carbazole or fluorene-functionalized diene or diacrylate monomers were synthesized. All of these copolymers were tailored to explore the effects of alternating and random monomer sequences and electron transfer capability on the self-assembly morphology and photoresponsive properties. As expected, the distinct absorption features from azo units in these copolymers are observed in their optical spectra, which cannot be achieved by traditional azo-containing homo- and copolymers. Because of the presence of stiff and electron-rich carbazole or fluorene motifs, the ability and efficiency of photoisomerization was depressed to some extent according to the sequential differences of two monomers and the electron effect in the copolymer chain. Moreover, the sizes and morphologies of alternating copolymers can be modulated through the methylene spacer and sequence of rigid conjugated motifs generating diverse nanostructures leading to a different chain mobility, which ultimately exhibited the unique photoisomerization behaviors. These interesting findings not only demonstrate a facile and efficient method for constructing azo-carbazole and azo-fluorene metathesis copolymers but also expand the optical properties of azo-containing polymers.

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Multi‐responsive Electropolymer Surface Coatings Based on Azo Molecular Switches and Carbazoles: Light, pH, and Electrochemical Control of Z→E Isomerization in Thin Films

Gibalova

Kortekaas

Simke

et al. 2023

Chemistry A European J

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Light‐responsive surfaces are attracting increasing interest, not least because their physicochemical properties can be selectively and temporally controlled by a non‐invasive stimulus. Most existing immobilization strategies involve the chemical attachment of light‐responsive moieties to the surface, although this approach often suffers from a low surface concentration of active species or a high inhomogeneity of applied coatings. Herein we present electropolymerization of carbazoles as a facile and rapid approach for preparing light‐responsive azo‐based surface coatings. The electrochemical oxidative polymerization of bis‐carbazole containing azo‑monomers yields stable films in which the photochemical properties and specific pH sensitivity of azo molecular switches are retained. Moreover, the molecular design enables electrocatalytic control over Z → E azo double bond isomerization facilitated by the conductive polycarbazole backbone. Ultimately, the high degree of control over macromolecular properties yields conductive surface coatings responsive to a range of stimuli, showing great promise as a strategy for versatile application in organic electronics.

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Synthesis of methyl‐substituted azobenzene–carbazole conjugated copolymers with photoinduced structural changes

Cited by 6 publications

References 27 publications

Electrochromism of Main‐Chain Polyazobenzenes Synthesized in Liquid Crystal Template and Its Orientation Behavior

Electrochromism of Main‐Chain Polyazobenzenes Synthesized in Liquid Crystal Template and Its Orientation Behavior

Azobenzene-containing Alternating and Random Metathesis Copolymers toward Gaining More Insight into Photoisomerization Properties

Multi‐responsive Electropolymer Surface Coatings Based on Azo Molecular Switches and Carbazoles: Light, pH, and Electrochemical Control of Z→E Isomerization in Thin Films

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