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Combined Experimental and Theoretical Studies on Planar Chirality of Partially Overlapped C2-Symmetric [3.3](3,9)Dicarbazolophanes.
The Journal of Physical Chemistry A ( IF 2.7 ) Pub Date : 2020-03-03 , DOI: 10.1021/acs.jpca.0c00286 Keita Tani 1 , Risa Imafuku 1 , Kanae Miyanaga 1 , Miyuki Eiraku Masaki 1 , Haruka Kato 1 , Kazushige Hori 1 , Koji Kubono 1 , Masatsugu Taneda 1 , Takunori Harada 2 , Kenta Goto 3 , Fumito Tani 3 , Tadashi Mori 4
The Journal of Physical Chemistry A ( IF 2.7 ) Pub Date : 2020-03-03 , DOI: 10.1021/acs.jpca.0c00286 Keita Tani 1 , Risa Imafuku 1 , Kanae Miyanaga 1 , Miyuki Eiraku Masaki 1 , Haruka Kato 1 , Kazushige Hori 1 , Koji Kubono 1 , Masatsugu Taneda 1 , Takunori Harada 2 , Kenta Goto 3 , Fumito Tani 3 , Tadashi Mori 4
Affiliation
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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.
中文翻译：
部分重叠的C2对称[3.3]（3,9）Dicarbazolophanes的平面手性的实验和理论研究相结合。
部分重叠的双咔唑并具有平面手性。在这项研究中，C2对称[3.3]（3,9）二咔唑啉衍生物（CZ1-CZ3）首次通过制备型手性高效液相色谱光学拆分。在其圆二色性（CD）光谱中，观察到适度的Cotton效应（CEs）的1Lb和1La跃迁（|Δε|分别为10-12和51-57 M-1 cm-1），同时发现了强烈的CEs在其1B跃迁（|Δε| = 156-216 M-1 cm-1）中，吸收不对称（gab）因子约为10-2。还获得了氰酰胺衍生物CZ1的圆偏振发光光谱，其相对发光不对称系数（glum）为0.013。应用计算机研究来解决这些平面手性二咔唑啉类中显着的手性响应的因素。通过实验和理论CD光谱的比较，明确确定了绝对构型，对映体纯磺酰胺衍生物CZ2的X射线晶体结构分析证实了这一点。
更新日期：2020-03-03
中文翻译：
部分重叠的C2对称[3.3]（3,9）Dicarbazolophanes的平面手性的实验和理论研究相结合。
部分重叠的双咔唑并具有平面手性。在这项研究中，C2对称[3.3]（3,9）二咔唑啉衍生物（CZ1-CZ3）首次通过制备型手性高效液相色谱光学拆分。在其圆二色性（CD）光谱中，观察到适度的Cotton效应（CEs）的1Lb和1La跃迁（|Δε|分别为10-12和51-57 M-1 cm-1），同时发现了强烈的CEs在其1B跃迁（|Δε| = 156-216 M-1 cm-1）中，吸收不对称（gab）因子约为10-2。还获得了氰酰胺衍生物CZ1的圆偏振发光光谱，其相对发光不对称系数（glum）为0.013。应用计算机研究来解决这些平面手性二咔唑啉类中显着的手性响应的因素。通过实验和理论CD光谱的比较，明确确定了绝对构型，对映体纯磺酰胺衍生物CZ2的X射线晶体结构分析证实了这一点。
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