Combined Experimental and Theoretical Studies on Planar Chirality of Partially Overlapped C2-Symmetric [3.3](3,9)Dicarbazolophanes

Keita Tani, Risa Imafuku, Kanae Miyanaga, Miyuki Eiraku Masaki, Haruka Kato, Kazushige Hori, Koji Kubono, Masatsugu Taneda, Takunori Harada, Kenta Goto, Fumito Tani, Tadashi Mori

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3 Citations (Scopus)

Abstract

Partially overlapped dicarbazolophanes exhibit a planar chirality. In this study, C2-symmetrical [3.3](3,9)dicarbazolophane derivatives (CZ1-CZ3) have been optically resolved by preparative chiral high-performance liquid chromatography for the first time. In their circular dichroism (CD) spectra, moderate Cotton effects (CEs) were observed for their 1Lb and 1La transitions (|Δϵ| = 10-12 and 51-57 M-1 cm-1, respectively), while intense CEs were notified in their 1B transitions (|Δϵ| = 156-216 M-1 cm-1), absorption dissymmetry (gabs) factors being in orders of 10-2. Circularly polarized luminescence spectrum was also obtained for cyanamide derivative CZ1, with a comparative luminescence dissymmetry (glum) factor of 0.013. A computational investigation was applied to address the factors for such remarkable chiroptical responses in these dicarbazolophanes of planar chirality. Absolute configurations were unambiguously determined by the comparison of experimental and theoretical CD spectra, which was affirmed by the X-ray crystal structural analysis of enantiomerically pure sulfonamide derivative CZ2.

Original languageEnglish
Pages (from-to)2057-2063
Number of pages7
JournalJournal of Physical Chemistry A
Volume124
Issue number10
DOIs
Publication statusPublished - Mar 12 2020

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry

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