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Nogita R, Matohara K, Yamaji M, et al. Photochemical study of [3(3)](1,3,5)cyclophane and emission spectral properties of [3n]cyclophanes (n = 2-6). J Am Chem Soc. 2004;126(42):13732-41doi: 10.1021/ja030032x.
Nogita, R., Matohara, K., Yamaji, M., Oda, T., Sakamoto, Y., Kumagai, T., Lim, C., Yasutake, M., Shimo, T., Jefford, C. W., & Shinmyozu, T. (2004). Photochemical study of [3(3)](1,3,5)cyclophane and emission spectral properties of [3n]cyclophanes (n = 2-6). Journal of the American Chemical Society, 126(42), 13732-41. https://doi.org/10.1021/ja030032x
Nogita, Rika, et al. "Photochemical study of [3(3)](1,3,5)cyclophane and emission spectral properties of [3n]cyclophanes (n = 2-6)." Journal of the American Chemical Society vol. 126,42 (2004): 13732-41. doi: https://doi.org/10.1021/ja030032x
Nogita R, Matohara K, Yamaji M, Oda T, Sakamoto Y, Kumagai T, Lim C, Yasutake M, Shimo T, Jefford CW, Shinmyozu T. Photochemical study of [3(3)](1,3,5)cyclophane and emission spectral properties of [3n]cyclophanes (n = 2-6). J Am Chem Soc. 2004 Oct 27;126(42):13732-41. doi: 10.1021/ja030032x. PMID: 15493932.
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J Am Chem Soc. 2004 Oct 27;126(42):13732-41. doi: 10.1021/ja030032x.

Photochemical study of [3(3)](1,3,5)cyclophane and emission spectral properties of [3n]cyclophanes (n = 2-6).

Journal of the American Chemical Society

Rika Nogita, Kumi Matohara, Minoru Yamaji, Takuma Oda, Youichi Sakamoto, Tsutomu Kumagai, Chultack Lim, Mikio Yasutake, Tetsuro Shimo, Charles W Jefford, Teruo Shinmyozu

Affiliations

  1. Institute for Materials Chemistry and Engineering (IMCE), Department of Molecular Chemistry, Graduate School of Sciences, Kyushu University, Hakozaki 6-10-1, Fukuoka 812-8581, Japan.

PMID: 15493932 DOI: 10.1021/ja030032x

Abstract

Thephotochemical reaction of [3(3)](1,3,5)cyclophane 2, which is a photoprecursor for the formation of propella[3(3)]prismane 18, was studied using a sterilizing lamp (254 nm). Upon photolysis in dry and wet CH2Cl2 or MeOH in the presence of 2 mol/L aqueous HCl solution, the cyclophane 2 afforded novel cage compounds comprised of new skeletons, tetracyclo[6.3.1.0.(2,7)0(4,11)]dodeca-5,9-diene 43, hexacyclo[6.4.0.0.(2,6)0.(4,11)0.(5,10)0(9,12)]dodecane 44, and pentacyclo[6.4.0.0.(2,6)0.(4,11)0(5,10)]dodecane 45. All of these products were confirmed by the X-ray structural analyses. A possible mechanism for the formation of these photoproducts via the hexaprismane derivative 18 is proposed. The photophysical properties in the excited state of the [3n]cyclophanes ([3n]CP, n = 2-6) were investigated by measuring the emission spectra and determining the quantum yields and lifetimes of the fluorescence. All [3n]CPs show excimeric fluorescence without a monomeric one. The lifetime of the excimer fluorescence becomes gradually longer with the increasing number of the trimethylene bridges. The [3n]CPs also shows excimeric phosphorescence spectra without vibrational structures for n = 2, 4, and 5, while phosphorescence is absent for n = 3 and 6. With an increase in symmetry of the benzene skeleton in the [3(3)]- and [3(6)]CPs, the probability of the radiation (phosphorescence) process from the lowest triplet state may drastically decrease.

Copyright 2004 American Chemical Society

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