Researches on 2, l, 3-thia- and selenadiazole

Pesin, V. G.; D'yachenko, S. A.

doi:10.1007/bf00742366

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“…The synthesis of the two- and three-layered [3.3]PCPs 1 and 2 was achieved by the ( p -ethylbenzenesulfonyl)methyl isocyanide (EbsMIC) coupling method (Scheme ) . The chloride 3 was coupled with the EbsMIC adduct 4 to give the two-layered PCP dione 5 (36%), which was converted by the Wolff−Kishner (WK) reduction to the corresponding two-layered [3.3]PCP 1 (57%). Similarly, the coupling of the chloride 3 and the two-layered EbsMIC adduct 6 (racemic) provided the three-layered PCP-dione 7 (racemic) (43%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure, and Electronic and Photophysical Properties of Two- and Three-Layered [3.3]Paracyclophane-Based Donor−Acceptor Systems(1)

Watanabe

Goto²,

Shibahara

et al. 2010

J. Org. Chem.

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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(2)COCH(2)- 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 -CH(2)COCH(2)- or -CH(2)CH(2)CH(2)- 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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Section: Resultsmentioning

confidence: 99%