From N,N-diphenyl-N-naphtho[2,1-b]thieno[2,3-b:3′,2′-d]dithiophene-5-yl-amine to propeller-shaped N,N,N-tri(naphtho[2,1-b]thieno[2,3-b:3′,2′-d]dithiophene-5-yl)-amine: syntheses and structures |
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Authors: | Chunli Li Yongqing Zhang Sheng Zhang Jianwu Shi Yuhe Kan Hua Wang |
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Institution: | 1. Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng 475004, China;2. Jiangsu Province Key Laboratory for Chemistry of Low Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, China |
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Abstract: | Three unique propeller-shaped helicenyl amines compounds: N,N-diphenyl-N-naphtho2,1-b]thieno2,3-b:3′,2′-d]dithiophene-5-yl-amine (1), N-phenyl-N,N-di(naphtho2,1-b]thieno2,3-b:3′,2′-d]dithiophene-5-yl)amine (2), and N,N,N-tri(naphtho2,1-b]thieno2,3-b:3′,2′-d]dithiophene-5-yl)amine (3) were efficiently synthesized by Wittig reaction and oxidative photocyclization. The crystal structures of 1, 2 and molecular configuration optimization (DFT-B3LYP/6-31+G(d)) of 3 reveal that the steric hindrance from the moiety of trithia5]helicene effectively forces the nitrogen atom and the three bonded carbon atoms to coplanar and the interplanar angles of the facing terminal thiophene ring and benzene ring becoming larger when the helical arm increased from 1 to 3. Electrochemical properties and UV–vis absorption behaviors of 1, 2, 3 were primarily determined by the moiety of trithia5]helicene. |
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Keywords: | Helicenyl amines Synthesis Crystal structures |
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