Synthesis, structure, and electronic and photophysical properties of two- and three-layered [3.3]Paracyclophane-based donor-acceptor systems (1)

Motonori Watanabe, Kenta Goto, Masahiko Shibahara, Teruo Shinmyozu

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Figure presented. The synthesis, structural, redox, and photophysical properties of the two- and three-layered donor-acceptor (D-A) type [3.3]paracyclophanes ([3.3]PCPs) are described. The synthesis of the two- and three-layered [3.3]PCPs 1 and 2 containing 2,1,3-benzothiadiazole (BTD) as an acceptor was achieved by the (p-ethylbenzenesulfonyl)methyl isocyanide coupling method. The cyclic voltammograms of 1 and 2 along with those of respective dione precursors 5 and 7 clearly indicate that the presence of the -CH 2COCH2- bridge interferes with the electronic interactions between the BTD and the benzene rings, suggesting the importance of the through-bond interaction in the ground state. In sharp contrast, the UV/vis spectra of 1 and 5 as well as those of 2 and 7 exhibit similar bands regardless of the presence of the -CH2COCH2- or -CH 2CH2CH2- bridges, indicating that the charge-transfer (CT) interaction is mainly responsible for the through-space interaction. The two-layered PCPs, 5 and 1, show broad structureless fluorescence bands at the same position of 468 nm, while those of the three-layered PCPs, 7 and 2, appear at 501 and 496 nm, respectively, with lower quantum yields compared to those of the two-layered PCPs probably due to the stronger intramolecular CT interaction of the three-layered PCPs in the ground state.

Original languageEnglish
Pages (from-to)6104-6114
Number of pages11
JournalJournal of Organic Chemistry
Volume75
Issue number18
DOIs
Publication statusPublished - Sep 17 2010

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Ground state
Charge transfer
Quantum yield
Benzene
Fluorescence
(2.2)paracyclophane
benzo-1,2,3-thiadiazole
methylisonitrile
Oxidation-Reduction

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Synthesis, structure, and electronic and photophysical properties of two- and three-layered [3.3]Paracyclophane-based donor-acceptor systems (1). / Watanabe, Motonori; Goto, Kenta; Shibahara, Masahiko; Shinmyozu, Teruo.

In: Journal of Organic Chemistry, Vol. 75, No. 18, 17.09.2010, p. 6104-6114.

Research output: Contribution to journalArticle

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abstract = "Figure presented. The synthesis, structural, redox, and photophysical properties of the two- and three-layered donor-acceptor (D-A) type [3.3]paracyclophanes ([3.3]PCPs) are described. The synthesis of the two- and three-layered [3.3]PCPs 1 and 2 containing 2,1,3-benzothiadiazole (BTD) as an acceptor was achieved by the (p-ethylbenzenesulfonyl)methyl isocyanide coupling method. The cyclic voltammograms of 1 and 2 along with those of respective dione precursors 5 and 7 clearly indicate that the presence of the -CH 2COCH2- bridge interferes with the electronic interactions between the BTD and the benzene rings, suggesting the importance of the through-bond interaction in the ground state. In sharp contrast, the UV/vis spectra of 1 and 5 as well as those of 2 and 7 exhibit similar bands regardless of the presence of the -CH2COCH2- or -CH 2CH2CH2- bridges, indicating that the charge-transfer (CT) interaction is mainly responsible for the through-space interaction. The two-layered PCPs, 5 and 1, show broad structureless fluorescence bands at the same position of 468 nm, while those of the three-layered PCPs, 7 and 2, appear at 501 and 496 nm, respectively, with lower quantum yields compared to those of the two-layered PCPs probably due to the stronger intramolecular CT interaction of the three-layered PCPs in the ground state.",
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