High stability poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) and phenyl vinylene thiophene electro-optic host-guest system

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Abstract

Poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) was prepared by ring opening metathesis polymerization. This was achieved in chloroform using the Grubbs 1st generation initiator and quenched with ethyl vinyl ether. The polymer had a weight average molecular weight of 27,000 g/mol with a polydispersity index of 2.19, a high glass transition temperature of 281 °C and a high thermal decomposition temperature of 385 °C (10% loss). The trans:cis vinylene ratio was 1.00:0.19 making the polymer amorphous. The polymer was used as a host for 5 guest nonlinear optical chromophores. The relationship between the chromophore structure and the electro-optic coefficient was investigated. A range of chromophore concentrations were evaluated and it was found that the ideal chromophore structure included a bulky tert-butyldiphenylsilane side group. A maximum r33 of 80 pm/V was obtained at a chromophore concentration of 45 wt% and a poling temperature of 160 °C. A host-guest system containing 35 wt% of the tert-butyldiphenylsilane substituted chromophore had a stability of 85% at a temperature of 85 °C for 500 h. The stability at 105 °C was 72%. In comparison amorphous polycarbonate under the same conditions achieved a stability of just 58% at 85 °C, while poly(methyl methacrylate) had a stability of 0% at 85 °C.

Original languageEnglish
Pages (from-to)89-99
Number of pages11
JournalEuropean Polymer Journal
Volume84
DOIs
Publication statusPublished - Nov 1 2016

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Thiophenes
Thiophene
Chromophores
Electrooptical effects
thiophenes
chromophores
electro-optics
Polymers
polycarbonate
polymers
metathesis
Ring opening polymerization
Polydispersity
Polymethyl Methacrylate
polycarbonates
initiators
Chloroform
Chlorine compounds
Polycarbonates
chloroform

All Science Journal Classification (ASJC) codes

  • Physics and Astronomy(all)
  • Polymers and Plastics
  • Organic Chemistry

Cite this

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title = "High stability poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) and phenyl vinylene thiophene electro-optic host-guest system",
abstract = "Poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) was prepared by ring opening metathesis polymerization. This was achieved in chloroform using the Grubbs 1st generation initiator and quenched with ethyl vinyl ether. The polymer had a weight average molecular weight of 27,000 g/mol with a polydispersity index of 2.19, a high glass transition temperature of 281 °C and a high thermal decomposition temperature of 385 °C (10{\%} loss). The trans:cis vinylene ratio was 1.00:0.19 making the polymer amorphous. The polymer was used as a host for 5 guest nonlinear optical chromophores. The relationship between the chromophore structure and the electro-optic coefficient was investigated. A range of chromophore concentrations were evaluated and it was found that the ideal chromophore structure included a bulky tert-butyldiphenylsilane side group. A maximum r33 of 80 pm/V was obtained at a chromophore concentration of 45 wt{\%} and a poling temperature of 160 °C. A host-guest system containing 35 wt{\%} of the tert-butyldiphenylsilane substituted chromophore had a stability of 85{\%} at a temperature of 85 °C for 500 h. The stability at 105 °C was 72{\%}. In comparison amorphous polycarbonate under the same conditions achieved a stability of just 58{\%} at 85 °C, while poly(methyl methacrylate) had a stability of 0{\%} at 85 °C.",
author = "Spring, {Andrew M.} and Feng Qiu and Shiyoshi Yokoyama",
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T1 - High stability poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) and phenyl vinylene thiophene electro-optic host-guest system

AU - Spring, Andrew M.

AU - Qiu, Feng

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N2 - Poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) was prepared by ring opening metathesis polymerization. This was achieved in chloroform using the Grubbs 1st generation initiator and quenched with ethyl vinyl ether. The polymer had a weight average molecular weight of 27,000 g/mol with a polydispersity index of 2.19, a high glass transition temperature of 281 °C and a high thermal decomposition temperature of 385 °C (10% loss). The trans:cis vinylene ratio was 1.00:0.19 making the polymer amorphous. The polymer was used as a host for 5 guest nonlinear optical chromophores. The relationship between the chromophore structure and the electro-optic coefficient was investigated. A range of chromophore concentrations were evaluated and it was found that the ideal chromophore structure included a bulky tert-butyldiphenylsilane side group. A maximum r33 of 80 pm/V was obtained at a chromophore concentration of 45 wt% and a poling temperature of 160 °C. A host-guest system containing 35 wt% of the tert-butyldiphenylsilane substituted chromophore had a stability of 85% at a temperature of 85 °C for 500 h. The stability at 105 °C was 72%. In comparison amorphous polycarbonate under the same conditions achieved a stability of just 58% at 85 °C, while poly(methyl methacrylate) had a stability of 0% at 85 °C.

AB - Poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) was prepared by ring opening metathesis polymerization. This was achieved in chloroform using the Grubbs 1st generation initiator and quenched with ethyl vinyl ether. The polymer had a weight average molecular weight of 27,000 g/mol with a polydispersity index of 2.19, a high glass transition temperature of 281 °C and a high thermal decomposition temperature of 385 °C (10% loss). The trans:cis vinylene ratio was 1.00:0.19 making the polymer amorphous. The polymer was used as a host for 5 guest nonlinear optical chromophores. The relationship between the chromophore structure and the electro-optic coefficient was investigated. A range of chromophore concentrations were evaluated and it was found that the ideal chromophore structure included a bulky tert-butyldiphenylsilane side group. A maximum r33 of 80 pm/V was obtained at a chromophore concentration of 45 wt% and a poling temperature of 160 °C. A host-guest system containing 35 wt% of the tert-butyldiphenylsilane substituted chromophore had a stability of 85% at a temperature of 85 °C for 500 h. The stability at 105 °C was 72%. In comparison amorphous polycarbonate under the same conditions achieved a stability of just 58% at 85 °C, while poly(methyl methacrylate) had a stability of 0% at 85 °C.

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