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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

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
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 - 14 Apr 2009

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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

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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.",

author = "Zhengwei Shi and Jingdong Luo and Su Huang and Yen-Ju Cheng and Kim, {Tae Dong} and Polishak, {Brent M.} and Zhou, {Xing Hua} and Yanqing Tian and Jang, {Sei Hum} and Knorr, {Daniel B.} and Overney, {Ren{\'e} M.} and Younkin, {Todd R.} and Jen, {Alex K.Y.}",

year = "2009",

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day = "14",

doi = "10.1021/ma802612g",

language = "English",

volume = "42",

pages = "2438--2445",

journal = "Macromolecules",

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Shi, Z, Luo, J, Huang, S, Cheng, Y-J, 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

TY - JOUR

T1 - Controlled diels alder reactions used to incorporate highly ef?cient polyenic chromophores into maleimide-containing side-chain polymers for electro-optics

AU - Shi, Zhengwei

AU - Luo, Jingdong

AU - Huang, Su

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.

PY - 2009/4/14

Y1 - 2009/4/14

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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JO - Macromolecules

JF - Macromolecules

IS - 7

ER -

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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