Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes

Hsin Chieh Lin; Jui Hung Hsu; Chao Kuei Lee; Oliver Yung Hui Tai; Chin Hsien Wang; Chih Ming Chou; Kuang Yen Chen; Yi Lin Wu; Tien Yau Luh

doi:10.1002/chem.200902115

Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes

Hsin Chieh Lin, Jui Hung Hsu^*, Chao Kuei Lee, Oliver Yung Hui Tai, Chin Hsien Wang, Chih Ming Chou, Kuang Yen Chen, Yi Lin Wu, Tien Yau Luh

^*Corresponding author for this work

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

10 Scopus citations

Abstract

Centrosymmetric furan-containing cyclophandienes 3 and 4, synthesized by our furan annulation protocol, have been shown to exhibit extraordinarily large Stokes shifts and second-order nonlinear optical β values. The β values for 3 and 4 measured at 1.32 mm are 208 and 530 × 10^-30 esu, respectively. The β values of 3 and 4 are similar to those of respective cyclophenes 1a and 7 in which strong hyperpoarizable interactions between two twisted π-systems (oligoaryl and bridging double bond) might take place. Symmetry breaking due to the resonance contribution (cf. 2) and the unique structural features of 3 and 4 has been used to account for this unusual photophysical behavior.

Original language	English (US)
Pages (from-to)	13201-13209
Number of pages	9
Journal	Chemistry - A European Journal
Volume	15
Issue number	47
DOIs	https://doi.org/10.1002/chem.200902115
State	Published - Dec 7 2009

Keywords

Cyclophandienes
Nonlinear optics
Oligoaryls
Photochemistry
Symmetry breaking

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

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10.1002/chem.200902115

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@article{c942e5c2009f417e846f255bef3c3156,

title = "Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes",

abstract = "Centrosymmetric furan-containing cyclophandienes 3 and 4, synthesized by our furan annulation protocol, have been shown to exhibit extraordinarily large Stokes shifts and second-order nonlinear optical β values. The β values for 3 and 4 measured at 1.32 mm are 208 and 530 × 10-30 esu, respectively. The β values of 3 and 4 are similar to those of respective cyclophenes 1a and 7 in which strong hyperpoarizable interactions between two twisted π-systems (oligoaryl and bridging double bond) might take place. Symmetry breaking due to the resonance contribution (cf. 2) and the unique structural features of 3 and 4 has been used to account for this unusual photophysical behavior.",

keywords = "Cyclophandienes, Nonlinear optics, Oligoaryls, Photochemistry, Symmetry breaking",

author = "Lin, {Hsin Chieh} and Hsu, {Jui Hung} and Lee, {Chao Kuei} and Tai, {Oliver Yung Hui} and Wang, {Chin Hsien} and Chou, {Chih Ming} and Chen, {Kuang Yen} and Wu, {Yi Lin} and Luh, {Tien Yau}",

year = "2009",

month = dec,

day = "7",

doi = "10.1002/chem.200902115",

language = "English (US)",

volume = "15",

pages = "13201--13209",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "47",

}

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T1 - Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes

AU - Lin, Hsin Chieh

AU - Hsu, Jui Hung

AU - Lee, Chao Kuei

AU - Tai, Oliver Yung Hui

AU - Wang, Chin Hsien

AU - Chou, Chih Ming

AU - Chen, Kuang Yen

AU - Wu, Yi Lin

AU - Luh, Tien Yau

PY - 2009/12/7

Y1 - 2009/12/7

N2 - Centrosymmetric furan-containing cyclophandienes 3 and 4, synthesized by our furan annulation protocol, have been shown to exhibit extraordinarily large Stokes shifts and second-order nonlinear optical β values. The β values for 3 and 4 measured at 1.32 mm are 208 and 530 × 10-30 esu, respectively. The β values of 3 and 4 are similar to those of respective cyclophenes 1a and 7 in which strong hyperpoarizable interactions between two twisted π-systems (oligoaryl and bridging double bond) might take place. Symmetry breaking due to the resonance contribution (cf. 2) and the unique structural features of 3 and 4 has been used to account for this unusual photophysical behavior.

AB - Centrosymmetric furan-containing cyclophandienes 3 and 4, synthesized by our furan annulation protocol, have been shown to exhibit extraordinarily large Stokes shifts and second-order nonlinear optical β values. The β values for 3 and 4 measured at 1.32 mm are 208 and 530 × 10-30 esu, respectively. The β values of 3 and 4 are similar to those of respective cyclophenes 1a and 7 in which strong hyperpoarizable interactions between two twisted π-systems (oligoaryl and bridging double bond) might take place. Symmetry breaking due to the resonance contribution (cf. 2) and the unique structural features of 3 and 4 has been used to account for this unusual photophysical behavior.

KW - Cyclophandienes

KW - Nonlinear optics

KW - Oligoaryls

KW - Photochemistry

KW - Symmetry breaking

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U2 - 10.1002/chem.200902115

DO - 10.1002/chem.200902115

M3 - Article

C2 - 19847830

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SN - 0947-6539

VL - 15

SP - 13201

EP - 13209

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 47

ER -

Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes

Abstract

Keywords

ASJC Scopus subject areas

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