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American Chemical Society, Journal of Organic Chemistry, 12(72), p. 4306-4312, 2007

DOI: 10.1021/jo070044r

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Chiral Molecular Switches Based on Binaphthalene Molecules with Anthracene Moieties: CD Signal Due to Interchromophoric Exciton Coupling and Modulation of the CD Spectrum

This paper is available in a repository.
This paper is available in a repository.

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Abstract

By coupling the features of binaphthalene and anthracene, new binaphthalenes with two anthracene moieties were designed and synthesized, aiming at developing chiral molecular switches. A strong CD signal with negative sign due to the interchromophoric exciton coupling was observed for (S)-1 with -(CH2)2 as the linker. This new CD signal became weak and the sign reversed by changing the linker to -(CH2)3 in (S)-2 and -(CH2)6 in (S)-3. For (S)-4 with -(CH2)11 as the linker, no such CD signal was detected. Photodimerization of two anthracene moieties in these binaphthalene molecules can occur. The results show that the CD spectra of (S)-1, (S)-2, (S)-3, and (R)-1 can be reversibly modulated by alternating UV light irradiation and heating. Therefore, chiral molecular switches based on new binaphthalenes with two anthracene moieties are achieved.