Synthesis and Aggregation Behavior of Poly(arylene alkenylene)s and Poly(arylene alkylene)s Having Dialkoxyphenylene and Aromatic Diimide Groups

Li Yi Tan, Yoshitaka Tsuchido, Kohtaro Osakada, Zhengguo Cai, Yoshiaki Takahashi, Daisuke Takeuchi

Research output: Contribution to journalArticle

Abstract

Polycondensation reactions of 2,5-dialkoxy-1,4-diiodobenzene with N,N′-ω-dialkenylpyromellitic diimide and N,N′- ω-dialkenyl naphthalenetetracarboxylic diimide in the presence of a Pd(OAc) 2 -NaOAc catalyst produce six polymers containing the two aromatic groups connected alternatingly by alkenylene spacers. 1 H NMR spectrum of a polymer prepared from 2,5-bis(dodecyloxy)-1,4-diiodobenzene and N,N′-(10-undecenyl)pyromellitic diimide (poly(1a-IA)) indicates that the polymerization involves 2,1- and 1,2-insertion of a vinyl group into the Pd-Ar bond in 70:30 selectivity. Matrix-assisted laser deportion/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) spectra of poly(1a-IA) and a polymer from 2,5-bis(dodecyloxy)-1,4-diiodobenzene with N,N′-dialkenyl naphthalenetetracarboxylic diimide (poly(1a-IIA)) contained a series of polymer fragments with M n up to 4500. Measurement of electrospray ionization MS (ESI-MS) of the polymers revealed formation of cyclic molecules for 1:1 and 2:2 oligomers. Hydrogenations of poly(1a-IA) by using [Ir(cod)(py)(PCy 3 )] + PF 6 - (cod = 1,5-cycloctadiene; PCy 3 = tricyclohexylphosphine) catalyst and of poly(1a-IIA) by a mixture of p-toluenesulfonyl hydrazide (TSH) and tripropylamine (TPA) produce the poly(arylene alkylene)s with saturated spacers in 93% degree of hydrogenation. The absorption spectrum of poly(1a-IA) in CHCl 3 shows an absorption edge at 410 nm, which is at a longer wavelength than that of a mixture of the monomers (370 nm). Light-scattering measurement of the solution (1.00 mmol L -1 ) indicates the presence of aggregates with a hydrodynamic radius of 48 nm. The polymers exhibit weak elasticity at room temperature, as determined by dynamic viscoelasticity analysis (DMA), and it becomes negligible on heating to 75-80 °C (polymer with pyromellitic diimide groups) and 110-122 °C (polymer with naphthalenetetracarboxylic diimide groups). The above properties of the polymers are attributed to attractive interaction between the electron-rich alkoxyphenylene and the electron-deficient aromatic diimide groups both in solution and in the solid state.

Original languageEnglish
Pages (from-to)1642-1652
Number of pages11
JournalMacromolecules
Volume52
Issue number4
DOIs
Publication statusPublished - Feb 26 2019

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Polymers
Agglomeration
Hydrogenation
Platelet Factor 3
Electrospray ionization
Catalysts
Electrons
Viscoelasticity
Polycondensation
Oligomers
Light scattering
Ionization
Mass spectrometry
Absorption spectra
Elasticity
Hydrodynamics
Monomers
Polymerization
Nuclear magnetic resonance
Heating

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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Synthesis and Aggregation Behavior of Poly(arylene alkenylene)s and Poly(arylene alkylene)s Having Dialkoxyphenylene and Aromatic Diimide Groups. / Tan, Li Yi; Tsuchido, Yoshitaka; Osakada, Kohtaro; Cai, Zhengguo; Takahashi, Yoshiaki; Takeuchi, Daisuke.

In: Macromolecules, Vol. 52, No. 4, 26.02.2019, p. 1642-1652.

Research output: Contribution to journalArticle

Tan, Li Yi ; Tsuchido, Yoshitaka ; Osakada, Kohtaro ; Cai, Zhengguo ; Takahashi, Yoshiaki ; Takeuchi, Daisuke. / Synthesis and Aggregation Behavior of Poly(arylene alkenylene)s and Poly(arylene alkylene)s Having Dialkoxyphenylene and Aromatic Diimide Groups. In: Macromolecules. 2019 ; Vol. 52, No. 4. pp. 1642-1652.
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abstract = "Polycondensation reactions of 2,5-dialkoxy-1,4-diiodobenzene with N,N′-ω-dialkenylpyromellitic diimide and N,N′- ω-dialkenyl naphthalenetetracarboxylic diimide in the presence of a Pd(OAc) 2 -NaOAc catalyst produce six polymers containing the two aromatic groups connected alternatingly by alkenylene spacers. 1 H NMR spectrum of a polymer prepared from 2,5-bis(dodecyloxy)-1,4-diiodobenzene and N,N′-(10-undecenyl)pyromellitic diimide (poly(1a-IA)) indicates that the polymerization involves 2,1- and 1,2-insertion of a vinyl group into the Pd-Ar bond in 70:30 selectivity. Matrix-assisted laser deportion/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) spectra of poly(1a-IA) and a polymer from 2,5-bis(dodecyloxy)-1,4-diiodobenzene with N,N′-dialkenyl naphthalenetetracarboxylic diimide (poly(1a-IIA)) contained a series of polymer fragments with M n up to 4500. Measurement of electrospray ionization MS (ESI-MS) of the polymers revealed formation of cyclic molecules for 1:1 and 2:2 oligomers. Hydrogenations of poly(1a-IA) by using [Ir(cod)(py)(PCy 3 )] + PF 6 - (cod = 1,5-cycloctadiene; PCy 3 = tricyclohexylphosphine) catalyst and of poly(1a-IIA) by a mixture of p-toluenesulfonyl hydrazide (TSH) and tripropylamine (TPA) produce the poly(arylene alkylene)s with saturated spacers in 93{\%} degree of hydrogenation. The absorption spectrum of poly(1a-IA) in CHCl 3 shows an absorption edge at 410 nm, which is at a longer wavelength than that of a mixture of the monomers (370 nm). Light-scattering measurement of the solution (1.00 mmol L -1 ) indicates the presence of aggregates with a hydrodynamic radius of 48 nm. The polymers exhibit weak elasticity at room temperature, as determined by dynamic viscoelasticity analysis (DMA), and it becomes negligible on heating to 75-80 °C (polymer with pyromellitic diimide groups) and 110-122 °C (polymer with naphthalenetetracarboxylic diimide groups). The above properties of the polymers are attributed to attractive interaction between the electron-rich alkoxyphenylene and the electron-deficient aromatic diimide groups both in solution and in the solid state.",
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T1 - Synthesis and Aggregation Behavior of Poly(arylene alkenylene)s and Poly(arylene alkylene)s Having Dialkoxyphenylene and Aromatic Diimide Groups

AU - Tan, Li Yi

AU - Tsuchido, Yoshitaka

AU - Osakada, Kohtaro

AU - Cai, Zhengguo

AU - Takahashi, Yoshiaki

AU - Takeuchi, Daisuke

PY - 2019/2/26

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N2 - Polycondensation reactions of 2,5-dialkoxy-1,4-diiodobenzene with N,N′-ω-dialkenylpyromellitic diimide and N,N′- ω-dialkenyl naphthalenetetracarboxylic diimide in the presence of a Pd(OAc) 2 -NaOAc catalyst produce six polymers containing the two aromatic groups connected alternatingly by alkenylene spacers. 1 H NMR spectrum of a polymer prepared from 2,5-bis(dodecyloxy)-1,4-diiodobenzene and N,N′-(10-undecenyl)pyromellitic diimide (poly(1a-IA)) indicates that the polymerization involves 2,1- and 1,2-insertion of a vinyl group into the Pd-Ar bond in 70:30 selectivity. Matrix-assisted laser deportion/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) spectra of poly(1a-IA) and a polymer from 2,5-bis(dodecyloxy)-1,4-diiodobenzene with N,N′-dialkenyl naphthalenetetracarboxylic diimide (poly(1a-IIA)) contained a series of polymer fragments with M n up to 4500. Measurement of electrospray ionization MS (ESI-MS) of the polymers revealed formation of cyclic molecules for 1:1 and 2:2 oligomers. Hydrogenations of poly(1a-IA) by using [Ir(cod)(py)(PCy 3 )] + PF 6 - (cod = 1,5-cycloctadiene; PCy 3 = tricyclohexylphosphine) catalyst and of poly(1a-IIA) by a mixture of p-toluenesulfonyl hydrazide (TSH) and tripropylamine (TPA) produce the poly(arylene alkylene)s with saturated spacers in 93% degree of hydrogenation. The absorption spectrum of poly(1a-IA) in CHCl 3 shows an absorption edge at 410 nm, which is at a longer wavelength than that of a mixture of the monomers (370 nm). Light-scattering measurement of the solution (1.00 mmol L -1 ) indicates the presence of aggregates with a hydrodynamic radius of 48 nm. The polymers exhibit weak elasticity at room temperature, as determined by dynamic viscoelasticity analysis (DMA), and it becomes negligible on heating to 75-80 °C (polymer with pyromellitic diimide groups) and 110-122 °C (polymer with naphthalenetetracarboxylic diimide groups). The above properties of the polymers are attributed to attractive interaction between the electron-rich alkoxyphenylene and the electron-deficient aromatic diimide groups both in solution and in the solid state.

AB - Polycondensation reactions of 2,5-dialkoxy-1,4-diiodobenzene with N,N′-ω-dialkenylpyromellitic diimide and N,N′- ω-dialkenyl naphthalenetetracarboxylic diimide in the presence of a Pd(OAc) 2 -NaOAc catalyst produce six polymers containing the two aromatic groups connected alternatingly by alkenylene spacers. 1 H NMR spectrum of a polymer prepared from 2,5-bis(dodecyloxy)-1,4-diiodobenzene and N,N′-(10-undecenyl)pyromellitic diimide (poly(1a-IA)) indicates that the polymerization involves 2,1- and 1,2-insertion of a vinyl group into the Pd-Ar bond in 70:30 selectivity. Matrix-assisted laser deportion/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) spectra of poly(1a-IA) and a polymer from 2,5-bis(dodecyloxy)-1,4-diiodobenzene with N,N′-dialkenyl naphthalenetetracarboxylic diimide (poly(1a-IIA)) contained a series of polymer fragments with M n up to 4500. Measurement of electrospray ionization MS (ESI-MS) of the polymers revealed formation of cyclic molecules for 1:1 and 2:2 oligomers. Hydrogenations of poly(1a-IA) by using [Ir(cod)(py)(PCy 3 )] + PF 6 - (cod = 1,5-cycloctadiene; PCy 3 = tricyclohexylphosphine) catalyst and of poly(1a-IIA) by a mixture of p-toluenesulfonyl hydrazide (TSH) and tripropylamine (TPA) produce the poly(arylene alkylene)s with saturated spacers in 93% degree of hydrogenation. The absorption spectrum of poly(1a-IA) in CHCl 3 shows an absorption edge at 410 nm, which is at a longer wavelength than that of a mixture of the monomers (370 nm). Light-scattering measurement of the solution (1.00 mmol L -1 ) indicates the presence of aggregates with a hydrodynamic radius of 48 nm. The polymers exhibit weak elasticity at room temperature, as determined by dynamic viscoelasticity analysis (DMA), and it becomes negligible on heating to 75-80 °C (polymer with pyromellitic diimide groups) and 110-122 °C (polymer with naphthalenetetracarboxylic diimide groups). The above properties of the polymers are attributed to attractive interaction between the electron-rich alkoxyphenylene and the electron-deficient aromatic diimide groups both in solution and in the solid state.

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