Donor-Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability

Yen-Ju Cheng; Jingdong Luo; Su Huang; Xinghua Zhou; Zhengwei Shi; Tae-Dong Kim; Denise H. Bale; Satsuki Takahashi; Andrew Yick; Brent M. Polishak; Sei-Hum Jang; Larry R. Dalton; Philip J. Reid; William H. Steier; Alex K.-Y. Jen

doi:10.1021/cm801097k

Donor-Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability

Yen-Ju Cheng, Jingdong Luo, Su Huang, Xinghua Zhou, Zhengwei Shi, Tae-Dong Kim, Denise H. Bale, Satsuki Takahashi, Andrew Yick, Brent M. Polishak, Sei-Hum Jang, Larry R. Dalton, Philip J. Reid, William H. Steier, Alex K.-Y. Jen

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

166 Citations (Scopus)

Abstract

We have successfully utilized epoxyisophorone ring-opening chemistry to efficiently incorporate the butylthio group to the phenyltetraene bridge of highly efficient nonlinear optical chromophores in high overall yield. By following the guidance of Dewar's rules, the sulfur atom functions as a moderate π-accepting group at a starred position of the conjugated bridge. Several of very critical material parameters of the phenyltetraenic chromophores for device applications have been intrinsically and simultaneously improved through such a simple and straightforward engineering of molecular structures. Compared with the nonsubstituted analogue 2, thiolated chromophore 1 achieves higher molecular hyperpolarizability (34%), enhanced E-O coefficient (38%), significantly improved photochemical stability against ¹O₂ (by an order of magnitude), and better optical transparency (17 nm blue-shifted λ_max absorption spectrum). © 2008 American Chemical Society.

Original language	English
Pages (from-to)	5047-5054
Journal	Chemistry of Materials
Volume	20
Issue number	15
Online published	4 Jul 2008
DOIs	https://doi.org/10.1021/cm801097k
Publication status	Published - 12 Aug 2008
Externally published	Yes

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Cheng, Y.-J., Luo, J., Huang, S., Zhou, X., Shi, Z., Kim, T.-D., Bale, D. H., Takahashi, S., Yick, A., Polishak, B. M., Jang, S.-H., Dalton, L. R., Reid, P. J., Steier, W. H., & Jen, A. K.-Y. (2008). Donor-Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability. Chemistry of Materials, 20(15), 5047-5054. https://doi.org/10.1021/cm801097k

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title = "Donor-Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability",

abstract = "We have successfully utilized epoxyisophorone ring-opening chemistry to efficiently incorporate the butylthio group to the phenyltetraene bridge of highly efficient nonlinear optical chromophores in high overall yield. By following the guidance of Dewar's rules, the sulfur atom functions as a moderate π-accepting group at a starred position of the conjugated bridge. Several of very critical material parameters of the phenyltetraenic chromophores for device applications have been intrinsically and simultaneously improved through such a simple and straightforward engineering of molecular structures. Compared with the nonsubstituted analogue 2, thiolated chromophore 1 achieves higher molecular hyperpolarizability (34%), enhanced E-O coefficient (38%), significantly improved photochemical stability against 1O2 (by an order of magnitude), and better optical transparency (17 nm blue-shifted λmax absorption spectrum). {\textcopyright} 2008 American Chemical Society.",

author = "Yen-Ju Cheng and Jingdong Luo and Su Huang and Xinghua Zhou and Zhengwei Shi and Tae-Dong Kim and Bale, {Denise H.} and Satsuki Takahashi and Andrew Yick and Polishak, {Brent M.} and Sei-Hum Jang and Dalton, {Larry R.} and Reid, {Philip J.} and Steier, {William H.} and Jen, {Alex K.-Y.}",

year = "2008",

month = aug,

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doi = "10.1021/cm801097k",

language = "English",

volume = "20",

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journal = "Chemistry of Materials",

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Cheng, Y-J, Luo, J, Huang, S, Zhou, X, Shi, Z, Kim, T-D, Bale, DH, Takahashi, S, Yick, A, Polishak, BM, Jang, S-H, Dalton, LR, Reid, PJ, Steier, WH & Jen, AK-Y 2008, 'Donor-Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability', Chemistry of Materials, vol. 20, no. 15, pp. 5047-5054. https://doi.org/10.1021/cm801097k

TY - JOUR

T1 - Donor-Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability

AU - Cheng, Yen-Ju

AU - Luo, Jingdong

AU - Huang, Su

AU - Zhou, Xinghua

AU - Shi, Zhengwei

AU - Kim, Tae-Dong

AU - Bale, Denise H.

AU - Takahashi, Satsuki

AU - Yick, Andrew

AU - Polishak, Brent M.

AU - Jang, Sei-Hum

AU - Dalton, Larry R.

AU - Reid, Philip J.

AU - Steier, William H.

AU - Jen, Alex K.-Y.

PY - 2008/8/12

Y1 - 2008/8/12

N2 - We have successfully utilized epoxyisophorone ring-opening chemistry to efficiently incorporate the butylthio group to the phenyltetraene bridge of highly efficient nonlinear optical chromophores in high overall yield. By following the guidance of Dewar's rules, the sulfur atom functions as a moderate π-accepting group at a starred position of the conjugated bridge. Several of very critical material parameters of the phenyltetraenic chromophores for device applications have been intrinsically and simultaneously improved through such a simple and straightforward engineering of molecular structures. Compared with the nonsubstituted analogue 2, thiolated chromophore 1 achieves higher molecular hyperpolarizability (34%), enhanced E-O coefficient (38%), significantly improved photochemical stability against 1O2 (by an order of magnitude), and better optical transparency (17 nm blue-shifted λmax absorption spectrum). © 2008 American Chemical Society.

AB - We have successfully utilized epoxyisophorone ring-opening chemistry to efficiently incorporate the butylthio group to the phenyltetraene bridge of highly efficient nonlinear optical chromophores in high overall yield. By following the guidance of Dewar's rules, the sulfur atom functions as a moderate π-accepting group at a starred position of the conjugated bridge. Several of very critical material parameters of the phenyltetraenic chromophores for device applications have been intrinsically and simultaneously improved through such a simple and straightforward engineering of molecular structures. Compared with the nonsubstituted analogue 2, thiolated chromophore 1 achieves higher molecular hyperpolarizability (34%), enhanced E-O coefficient (38%), significantly improved photochemical stability against 1O2 (by an order of magnitude), and better optical transparency (17 nm blue-shifted λmax absorption spectrum). © 2008 American Chemical Society.

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U2 - 10.1021/cm801097k

DO - 10.1021/cm801097k

M3 - RGC 21 - Publication in refereed journal

SN - 0897-4756

VL - 20

SP - 5047

EP - 5054

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 15

ER -

Donor-Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability

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