Photoresponsivity of asymmetrical dihydropyrene under circularly polarized light irradiation. (22nd June 2022)

• Record Type: Journal Article
• Authors: Sawada, Tsuyoshi; Kubo, Shingo; Nanamura, Kazuaki
• Is Part Of: Tetrahedron letters. Volume 100(2022)
• Publication Date: 2022-06-22
• Subjects: Photochromic Material -- Circular Polarized Light -- Dihydropyrene -- Molar circular polarized dichroism; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153880
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Asymmetric 2, 7-di- tert -butyl-10b, 10c-dimethyl-2′, 3′-dimethyl-pyrazino[2, 3- e ]dihydropyrene (DMPZ-DHP) was prepared by the annulation of diamino dihydropyrene with 2, 3-butanedione. Optical resolution was achieved using chiral high-performance liquid chromatography systems after the photoisomerization of DMPZ-DHP to DMPZ-metacyclophane-diene (MCPD), and its Kuhn's anisotropy factor (g = Δε/ε) was determined to be approximately 1.0 e −3 at 550 nm. [S]- and [R]-DMPZ-DHP were irradiated with 550nm left and right circularly polarized light (CPL), and photoisomerization was found to proceed more rapidly upon irradiating the [S]-isomer with right-CPL than with left-CPL and upon irradiating the [R]-isomer with left-CPL than with right-CPL. This suggests that CPL can be detected and analyzed using asymmetric DMPZ-DHP.