Photoresponsivity of asymmetrical dihydropyrene under circularly polarized light irradiation

[Display omitted] 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 p...

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Bibliographic Details
Published in:Tetrahedron letters 2022-06, Vol.100, p.153880, Article 153880
Main Authors: Sawada, Tsuyoshi, Kubo, Shingo, Nanamura, Kazuaki
Format: Article
Language:English
Subjects:
Circular Polarized Light
Dihydropyrene
Molar circular polarized dichroism
Photochromic Material
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153880