Chiral molecular switches based on binaphthalene molecules with anthracene moieties: CD signal due to interchromophoric exciton coupling and modulation of the CD spectrum

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.