Synthesis and structures of two novel indolo[3,2-b] carbazole derivatives |
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Authors: | Qun Zhang Yan Ren Chen Ma Dong-Ju Zhang Da-Te Li Xu-Tang Tao Min-Hua Jiang |
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Institution: | (1) State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, China;(2) Department of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China |
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Abstract: | Indolocarbazole derivatives have already been reported to be good organic semiconductor candidates. The knowledge of the relationship between the structure and packing of molecules in crystal is indispensable in design of high performance organic semiconductor materials. Two new indolocarbazole derivatives, 2,8-dibromo-5,11-di-4-(isoindole-1,3-dione-2-yl)butyl]indolo3,2-b]carbazole (I) and 2,8,6,12-tetrabromo-5,11-di-(4-chlorobutyl)indolo3,2-b]carbazole (II) have been synthesized and the crystal structures have been studied. The dichloromethane solvate of (I), C42H32Br2N4O4 · 2CH2Cl2, is monoclinic, space groups P21/n. Unit cell parameters are a = 11.6847(2), b = 12.6942(2), c = 13.7899(2) Å, β = 91.8220(10)°. Unlike other indolo3,2-b]carbazole derivatives, there is no any π–π stacking between the indolocarbazole backbone of two adjacent molecules in the crystal. Since the isoindole-1,3-dione-2-yl is introduced in 5- and 11-positions in the molecule, the intermolecular short contacts mainly localize in between the pendant groups of the neighboring indolocarbazole molecules. The compound (II) is also monoclinic with P21/c space groups. Unit cell parameters are a = 4.6427(9), b = 11.425(2), c = 24.511(4) Å, β = 93.47(1)°. In contrast with compound (I), the molecules of (II) possess strong face-to-face π–π stacking. The crystal structures were studied in detail. It is concluded that linear pedant groups benefit to co-facial π–π interaction. Additionally, the molecule electronic spectra were studied by quantum chemistry theoretical calculation. |
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Keywords: | Indolo[3 2-b]carbazole Synthesis X-ray diffraction Theoretical calculation Electronic spectrum |
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