Controlled diels alder reactions used to incorporate highly ef?cient polyenic chromophores into maleimide-containing side-chain polymers for electro-optics

Zhengwei Shi; Jingdong Luo; Su Huang; Yen Ju Cheng; Tae Dong Kim; Brent M. Polishak; Xing Hua Zhou; Yanqing Tian; Sei Hum Jang; Daniel B. Knorr; René M. Overney; Todd R. Younkin; Alex K.Y. Jen

doi:10.1021/ma802612g

Controlled diels alder reactions used to incorporate highly ef?cient polyenic chromophores into maleimide-containing side-chain polymers for electro-optics

Zhengwei Shi, Jingdong Luo, Su Huang, Yen Ju Cheng, Tae Dong Kim, Brent M. Polishak, Xing Hua Zhou, Yanqing Tian, Sei Hum Jang, Daniel B. Knorr, René M. Overney, Todd R. Younkin, Alex K.Y. Jen

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37 Scopus citations

Abstract

Using an in situ Diels Alder (DA) "click chemistry" strategy for reactions between anthracene and maleimide functional groups, two prototypes of novel nonlinear optical (NLO) side-chain polymers (PMI-A7 and PMI-B7) containing highly hyperpolarizable but chemically sensitive phenyltetraene-based chromophores were synthesized and their nonlinear optical and thermal properties were characterized. Through rational material design, these NLO side-chain polymers exhibited good processibility, large electro-optic (E-O) coef?cients (r33, of up to 263 and 287 pm/V at 1.31 μ m wavelength respectively), and excellent temporal stability. These combined properties make them promising materials for E-O device applications. Compared to PMI-B7, PMI-A7 exhibited signi?cantly enhanced temporal stability (87% of the initial r33 values was retained after 550 h at 85 °C) and solvent resistance, which was attributed to slight cross-linking from the side reaction between maleimide and phenyltetraenic chromophore moieties. This study showed that it is possible to take advantage of some side reactions to enhance the performance of NLO materials.

Original language	English (US)
Pages (from-to)	2438-2445
Number of pages	8
Journal	Macromolecules
Volume	42
Issue number	7
DOIs	https://doi.org/10.1021/ma802612g
State	Published - Apr 14 2009
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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Shi, Z., Luo, J., Huang, S., Cheng, Y. J., Kim, T. D., Polishak, B. M., Zhou, X. H., Tian, Y., Jang, S. H., Knorr, D. B., Overney, R. M., Younkin, T. R., & Jen, A. K. Y. (2009). Controlled diels alder reactions used to incorporate highly ef?cient polyenic chromophores into maleimide-containing side-chain polymers for electro-optics. Macromolecules, 42(7), 2438-2445. https://doi.org/10.1021/ma802612g

Shi, Z, Luo, J, Huang, S, Cheng, YJ, Kim, TD, Polishak, BM, Zhou, XH, Tian, Y, Jang, SH, Knorr, DB, Overney, RM, Younkin, TR & Jen, AKY 2009, 'Controlled diels alder reactions used to incorporate highly ef?cient polyenic chromophores into maleimide-containing side-chain polymers for electro-optics', Macromolecules, vol. 42, no. 7, pp. 2438-2445. https://doi.org/10.1021/ma802612g

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title = "Controlled diels alder reactions used to incorporate highly ef?cient polyenic chromophores into maleimide-containing side-chain polymers for electro-optics",

abstract = "Using an in situ Diels Alder (DA) {"}click chemistry{"} strategy for reactions between anthracene and maleimide functional groups, two prototypes of novel nonlinear optical (NLO) side-chain polymers (PMI-A7 and PMI-B7) containing highly hyperpolarizable but chemically sensitive phenyltetraene-based chromophores were synthesized and their nonlinear optical and thermal properties were characterized. Through rational material design, these NLO side-chain polymers exhibited good processibility, large electro-optic (E-O) coef?cients (r33, of up to 263 and 287 pm/V at 1.31 μ m wavelength respectively), and excellent temporal stability. These combined properties make them promising materials for E-O device applications. Compared to PMI-B7, PMI-A7 exhibited signi?cantly enhanced temporal stability (87% of the initial r33 values was retained after 550 h at 85 °C) and solvent resistance, which was attributed to slight cross-linking from the side reaction between maleimide and phenyltetraenic chromophore moieties. This study showed that it is possible to take advantage of some side reactions to enhance the performance of NLO materials.",

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AU - Shi, Zhengwei

AU - Luo, Jingdong

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AU - Cheng, Yen Ju

AU - Kim, Tae Dong

AU - Polishak, Brent M.

AU - Zhou, Xing Hua

AU - Tian, Yanqing

AU - Jang, Sei Hum

AU - Knorr, Daniel B.

AU - Overney, René M.

AU - Younkin, Todd R.

AU - Jen, Alex K.Y.

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N2 - Using an in situ Diels Alder (DA) "click chemistry" strategy for reactions between anthracene and maleimide functional groups, two prototypes of novel nonlinear optical (NLO) side-chain polymers (PMI-A7 and PMI-B7) containing highly hyperpolarizable but chemically sensitive phenyltetraene-based chromophores were synthesized and their nonlinear optical and thermal properties were characterized. Through rational material design, these NLO side-chain polymers exhibited good processibility, large electro-optic (E-O) coef?cients (r33, of up to 263 and 287 pm/V at 1.31 μ m wavelength respectively), and excellent temporal stability. These combined properties make them promising materials for E-O device applications. Compared to PMI-B7, PMI-A7 exhibited signi?cantly enhanced temporal stability (87% of the initial r33 values was retained after 550 h at 85 °C) and solvent resistance, which was attributed to slight cross-linking from the side reaction between maleimide and phenyltetraenic chromophore moieties. This study showed that it is possible to take advantage of some side reactions to enhance the performance of NLO materials.

AB - Using an in situ Diels Alder (DA) "click chemistry" strategy for reactions between anthracene and maleimide functional groups, two prototypes of novel nonlinear optical (NLO) side-chain polymers (PMI-A7 and PMI-B7) containing highly hyperpolarizable but chemically sensitive phenyltetraene-based chromophores were synthesized and their nonlinear optical and thermal properties were characterized. Through rational material design, these NLO side-chain polymers exhibited good processibility, large electro-optic (E-O) coef?cients (r33, of up to 263 and 287 pm/V at 1.31 μ m wavelength respectively), and excellent temporal stability. These combined properties make them promising materials for E-O device applications. Compared to PMI-B7, PMI-A7 exhibited signi?cantly enhanced temporal stability (87% of the initial r33 values was retained after 550 h at 85 °C) and solvent resistance, which was attributed to slight cross-linking from the side reaction between maleimide and phenyltetraenic chromophore moieties. This study showed that it is possible to take advantage of some side reactions to enhance the performance of NLO materials.

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Controlled diels alder reactions used to incorporate highly ef?cient polyenic chromophores into maleimide-containing side-chain polymers for electro-optics

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