Abstract
A general, convergent approach to the synthesis of a series of stilbene- and azo-based donor-acceptor, second-order nonlinear optical (NLO) chromophores is reported. The synthetic strategy enables preparation of both acid- and base-reactive structures, yielding protected, diamine-functionalized chromophores which can be liberated using either acidic or alkaline regents for incorporation into polyimide backbones. Three such chromophores, bis(4-aminophenyl)[4-(2-(4-nitrophenyl)vinyl)phenyl]amine, bis(4-aminophenyl)[4-(2-(6-nitrobenzothiazol-2-yl)vinyl)phenyl]amine, 2-[4-((4-(bis(4-aminophenyl)amino)phenyl)diazenyl)phenyl]-2-phenyl-1,1-dicyan oethylene, all having high thermal stabilites, were synthesized, characterized, and condensed with hexafluoroisopropylidene diphthalic anhydride or 2-(1,3-dioxoisobenzofuran-5-ylcarbonyloxy)ethyl 1,3-dioxoisobenzofuran-5-carboxylate to yield six high glass transition temperature polyimides (T(g) as high as 313 °C) for use as poled NLO materials. After casting as thin films, curing, and electric field corona poling, these materials exhibit χ((2)) (1064 nm) responses as high as 82.0 pm/V and negligible decay in response upon aging in air at 100 °C for over 1000 h.
| Original language | English |
|---|---|
| Pages (from-to) | 1679-1693 |
| Number of pages | 15 |
| Journal | Chemistry of Materials |
| Volume | 12 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Jun 2000 |
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ASJC Scopus subject areas
- Materials Science(all)
- Materials Chemistry
Cite this
Ultrahigh-temperature polymers for second-order nonlinear optics. Synthesis and properties of robust, processable, chromophore-embedded polyimides. / Davey, M. H.; Lee, V. Y.; Wu, L. M.; Moylan, C. R.; Volksen, W.; Knoesen, A.; Miller, R. D.; Marks, Tobin J.
In: Chemistry of Materials, Vol. 12, No. 6, 06.2000, p. 1679-1693.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Ultrahigh-temperature polymers for second-order nonlinear optics. Synthesis and properties of robust, processable, chromophore-embedded polyimides
AU - Davey, M. H.
AU - Lee, V. Y.
AU - Wu, L. M.
AU - Moylan, C. R.
AU - Volksen, W.
AU - Knoesen, A.
AU - Miller, R. D.
AU - Marks, Tobin J
PY - 2000/6
Y1 - 2000/6
N2 - A general, convergent approach to the synthesis of a series of stilbene- and azo-based donor-acceptor, second-order nonlinear optical (NLO) chromophores is reported. The synthetic strategy enables preparation of both acid- and base-reactive structures, yielding protected, diamine-functionalized chromophores which can be liberated using either acidic or alkaline regents for incorporation into polyimide backbones. Three such chromophores, bis(4-aminophenyl)[4-(2-(4-nitrophenyl)vinyl)phenyl]amine, bis(4-aminophenyl)[4-(2-(6-nitrobenzothiazol-2-yl)vinyl)phenyl]amine, 2-[4-((4-(bis(4-aminophenyl)amino)phenyl)diazenyl)phenyl]-2-phenyl-1,1-dicyan oethylene, all having high thermal stabilites, were synthesized, characterized, and condensed with hexafluoroisopropylidene diphthalic anhydride or 2-(1,3-dioxoisobenzofuran-5-ylcarbonyloxy)ethyl 1,3-dioxoisobenzofuran-5-carboxylate to yield six high glass transition temperature polyimides (T(g) as high as 313 °C) for use as poled NLO materials. After casting as thin films, curing, and electric field corona poling, these materials exhibit χ((2)) (1064 nm) responses as high as 82.0 pm/V and negligible decay in response upon aging in air at 100 °C for over 1000 h.
AB - A general, convergent approach to the synthesis of a series of stilbene- and azo-based donor-acceptor, second-order nonlinear optical (NLO) chromophores is reported. The synthetic strategy enables preparation of both acid- and base-reactive structures, yielding protected, diamine-functionalized chromophores which can be liberated using either acidic or alkaline regents for incorporation into polyimide backbones. Three such chromophores, bis(4-aminophenyl)[4-(2-(4-nitrophenyl)vinyl)phenyl]amine, bis(4-aminophenyl)[4-(2-(6-nitrobenzothiazol-2-yl)vinyl)phenyl]amine, 2-[4-((4-(bis(4-aminophenyl)amino)phenyl)diazenyl)phenyl]-2-phenyl-1,1-dicyan oethylene, all having high thermal stabilites, were synthesized, characterized, and condensed with hexafluoroisopropylidene diphthalic anhydride or 2-(1,3-dioxoisobenzofuran-5-ylcarbonyloxy)ethyl 1,3-dioxoisobenzofuran-5-carboxylate to yield six high glass transition temperature polyimides (T(g) as high as 313 °C) for use as poled NLO materials. After casting as thin films, curing, and electric field corona poling, these materials exhibit χ((2)) (1064 nm) responses as high as 82.0 pm/V and negligible decay in response upon aging in air at 100 °C for over 1000 h.
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U2 - 10.1021/cm990483+
DO - 10.1021/cm990483+
M3 - Article
VL - 12
SP - 1679
EP - 1693
JO - Chemistry of Materials
JF - Chemistry of Materials
SN - 0897-4756
IS - 6
ER -