Synthesis of novel thermally stable electrochromic polynorbornenes containing symmetrical diarylamine and unsymmetrical triarylamine chromophores via ring-opening metathesis polymerisation

Huang, Yu‐Hsuan; Wang, Kun‐Li; Lian, Wei-Ren; Liao, Yi-An; Liaw, Der‐Jang; Lee, Kueir‐Rarn; Lai, Juin‐Yih

doi:10.1016/j.polymer.2012.02.045

Cited by 6 publications

(5 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The TPA-substituted 1,6-heptadiyne monomers, M1 and M2 , were simply synthesized by etherification reaction of TPA-containing compound, which was prepared according to the literature procedure, with 4-toluenesulfonyl-1,6-heptadiyne or 4,4-bis(toluenesulfonyl)-1,6-heptadiyne as shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Metathesis Cyclopolymerization of 1,6-Heptadiyne Derivative toward Triphenylamine-Functionalized Polyacetylene with Excellent Optoelectronic Properties and Nanocylinder Morphology

et al. 2015

View full text Add to dashboard Cite

Metathesis cyclopolymerization of 1,6-heptadiyne derivatives is readily utilized to synthesize triphenylamine-functionalized polyacetylenes (TPA-PAs) by a third-generation Grubbs catalyst, which selectively generated TPA-PAs with a five-membered ring and all-trans microstructure. The TPA pendants endowed PAs with good solubility and excellent optoelectronic properties (maximum absorption wavelength of 592−605 nm in CHCl 3 , HOMO level of around −5.04 eV, and energy bandgap of 1.82−1.77 eV). When bis-TPA side group was introduced into the PA backbone, the resultant polymer, poly(M2), displayed desirable oxidative stability (up to 30 days stored in THF) and high fluorescence quantum yield (up to 12.3%) in the family of PA derivatives. In addition, poly(M2) could spontaneously self-assemble into the nanocylinder architecture without requiring any tedious postsynthetic treatments. This is the first report that the rigid and immobile conjugated PA segment assembled into the novel cylindrical nanostructure with the aid of π−π interaction of TPA side group.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Elucidation of these points is the subject of the current work. Since monomer with bis-substituents is more difficult to insert into the propagating carbene, and the propagating species containing the short conjugated carbene resulted in low conversion when MCP was performed . Thus, MCP was influenced deeply by a steric effect.…”

Section: Resultsmentioning

confidence: 99%

Metathesis Cyclopolymerization of 1,6-Heptadiyne Derivative toward Triphenylamine-Functionalized Polyacetylene with Excellent Optoelectronic Properties and Nanocylinder Morphology

et al. 2015

View full text Add to dashboard Cite

show abstract

“…In 2012, two unsymmetrical TPA derivatives with a naphthaleneephenyl pair were attached as the side groups at the first nitrogen position [61] (see 19 in Fig. 16, Table 3), so the hydrogenated PNBs contained symmetrical diarylamine and unsymmetrical triarylamine chromophores.…”

Section: Polynorbornenes (Pnbs)mentioning

confidence: 99%

Recent advances in electrochromic polymers

Abidin

Zhang

Wang

et al. 2014

Polymer

Self Cite

View full text Add to dashboard Cite

“…Among the electrochromic polymers, TAA and its derivatives are well-known materials due to their excellent properties such that easier film process, multicolor change, high contrast and rapid response and have gained great interest of scientists 11 . Liou, Hsiao, Liaw and other researchers have reported a large number of TAA-based electrochromic materials 12 – 17 . According to the previous study, the propeller-like TAA unit can play an important role in reducing intermolecular force, which is in favor of improving the solubility of polymers as well as increasing the photoelectric properties.…”

Section: Introductionmentioning

confidence: 99%

Organic-inorganic hybrid electrochromic materials, polysilsesquioxanes containing triarylamine, changing color from colorless to blue

Wang

Cai

et al. 2017

Sci Rep

View full text Add to dashboard Cite

Four kinds of soluble monomers, containing triarylamine (TAA) group with reactive siloxane group, were synthesized under mild conditions via the reaction between 3-(triethoxysilyl)propyl isocyanate (TEOSPIC) and four TAA derivatives, respectively. Then the corresponding colorless organic-inorganic hybrid materials (PSSOs) were derived from the hydrolytic condensation of the monomers. PSSOs revealed good solubility in polar solvents on account of the effect of propeller-like TAA unit as well as the auxo-action effect of the flexible chain within the monomers. The structural characteristics of these PSSOs were identified by 1H NMR, 29Si NMR, FT-IR spectroscopies and X-ray diffraction (XRD). The morphology, dynamic changes of the transmittance and current before and after electro-oxidizing reaction were studied, and didn’t show significant change suggesting good stability of the PSSOs. Meanwhile, these PSSOs performed high contrast of optical transmittance change up to 84% with the highest coloration efficiency to 241 cm2·C−1. Furthermore, electrofluorescent properties of PSSOs were investigated with high-contrast.

show abstract

Synthesis of novel thermally stable electrochromic polynorbornenes containing symmetrical diarylamine and unsymmetrical triarylamine chromophores via ring-opening metathesis polymerisation

Cited by 6 publications

References 42 publications

Metathesis Cyclopolymerization of 1,6-Heptadiyne Derivative toward Triphenylamine-Functionalized Polyacetylene with Excellent Optoelectronic Properties and Nanocylinder Morphology

Metathesis Cyclopolymerization of 1,6-Heptadiyne Derivative toward Triphenylamine-Functionalized Polyacetylene with Excellent Optoelectronic Properties and Nanocylinder Morphology

Recent advances in electrochromic polymers

Organic-inorganic hybrid electrochromic materials, polysilsesquioxanes containing triarylamine, changing color from colorless to blue

Contact Info

Product

Resources

About