期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 18, 页码 6104-6114出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo100688m
关键词
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资金
- Institute of Chemistry, Academia Sinica, Taiwan R.O.C.
- Ministry of Education, Culture, Sports, Science and Technology, Japan [21106015]
- Venture-Business Laboratory, Kyushu University
- Grants-in-Aid for Scientific Research [21106015] Funding Source: KAKEN
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-ethylbenzenesulfonypmethyl isocyanide coupling method. The cyclic voltammo-grams of 1 and 2 along with those of respective dione precursors 5 and 7 clearly indicate that the presence of the -CH2COCH2- 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 -CH2CH2CH2- 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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