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Synthesis, crystal structure and spectroscopic properties of an unsymmetrical compound with carbazole and benzothiadiazole units |
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| Authors: | Qingguo He Yuxi Sun Shengang Xu Jiangong Cheng |
| Affiliation: | a Key Laboratory of Organic Solids, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China b Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences, Shanghai 200050, China c Department of Chemistry, Qufu Normal university, Qufu 273100, Shandong, China d School of Materials and Engineering, Zhengzhou University, Zhengzhou 450052, Henan, China |
| Abstract: | An unsymmetrical organic compound with carbazole (Cz) as donor and benzothiadiazole (BTD) as acceptor (D-π-A-π∗-D∗) was designed and synthesized via simple Heck reaction. The unique crystal structure of Cz-BTD-Cz∗ shows a ladder-like packing mode. A two molecule pair stacks parallelly with each other in each packing unit. In each cell, one Cz moiety is connected with BTD by vinylene bond in same plane. However, the other Cz group is connected to BTD by a one-end vinyl bond in almost perpendicular position to the coplanar part of the molecule. The shortest intermolecular plane distance is 3.48 ± 0.1 Å. The photophysical properties of Cz-BTD-Cz∗ in solution and in bulky crystalline powder state were studied. In bulk crystalline powder state, it has a red-shifted emission band peaked at 609 nm relative to that in solution, and the FWHM was reduced to only 58 nm. Electrochemical properties were also investigated. |
| Keywords: | Heck reaction Charge transfer state Unsymmetrical Photophysical property |
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