Volume 8, Issue 18 p. 2671-2677
Article

Two-Photon Absorption Properties of Dehydrobenzo[12]annulenes and Hexakis(phenylethynyl)benzenes: Effect of Edge-Linkage

Kenji Kamada Dr.

Kenji Kamada Dr.

Photonics Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, Japan, Fax: (+81) 72-751-9637

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Liudmil Antonov Prof.

Liudmil Antonov Prof.

Photonics Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, Japan, Fax: (+81) 72-751-9637

Institute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str. bl. 9, Sofia 1113, Bulgaria

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Satoru Yamada Dr.

Satoru Yamada Dr.

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan

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Koji Ohta Dr.

Koji Ohta Dr.

Photonics Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, Japan, Fax: (+81) 72-751-9637

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Takashi Yoshimura

Takashi Yoshimura

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

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Kazukuni Tahara Prof.

Kazukuni Tahara Prof.

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

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Akiko Inaba

Akiko Inaba

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

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Motohiro Sonoda Prof.

Motohiro Sonoda Prof.

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

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Yoshito Tobe Prof.

Yoshito Tobe Prof.

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

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First published: 13 December 2007
Citations: 29

Graphical Abstract

Linking-up: A multiply-fused [12]annulene exhibits a large two-photon absorption (TPA) cross section of 1300 GM, which is twice as large as that of the compound without linkage between the peripheral phenyl rings (see figure). The TPA activity of the compounds is primarily explained in terms of the planarity of the molecules in relation with the type of edge-linkage.

Abstract

Two-photon absorption (TPA) properties of two trefoil-shaped compounds with different edge linkages—tris(hexadehydrotribenzo[12]annulene) and tris(tetradehydrotribenzo[12]annulene)—and three asterisk-shaped compounds having no edge-linkage—hexakis(phenylethynyl)benzenes—are investigated experimentally by the open-aperture Z-scan and TPA-induced fluorescence methods with wavelength tuneable femtosecond pulses. The compound with ethynylene edge-linkage exhibits the most intense TPA (the maximal TPA cross section is 1300±170 GM at 572 nm where 1 GM=10−50 cm4s molecule−1 photon−1). The TPA activity of the compounds is primarily explained in terms of the planarity of the molecules in relation with the type of edge-linkage.