Derivation of saddle shaped cyclooctatetrathiophene: increasing conjugation and fabricating pentamer |
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| Authors: | Yong Wang Dewen Gao Jianwu Shi Yuhe Kan Jinsheng Song Chunli Li Hua Wang |
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| Institution: | 1. Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng 475004, China;2. Institute of Environmental and Analytical Sciences, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China;3. 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: | With cyclooctatetrathiophene (COTh) as building block, two α,α,α,α-tetraaryl COThs, COThP and COThTh have been efficiently synthesized. Phenyl and thienyl were employed as end-capping groups to introduce to COTh and increase its conjugation. For enlarging the special ‘saddle’ shaped structure, a pentamer of COTh was synthesized via Negishi reaction and CuCl2-promoted oxidative coupling reaction. The pentamer (COThF) is a new type of dendrimer with COTh as dendron, which presents an artistic configuration possessing a large saddle shape. All compounds were fully characterized by 1H NMR, 13C NMR, HRMS and IR. The crystal structures of COThP and COThTh were confirmed by X-ray analysis. The molecular configuration of COThF was optimized by theoretical calculations. Their UV–vis properties, electrochemical behaviours and thermo-gravimetric analysis of COThP, COThTh and COThF were also described. |
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| Keywords: | Cyclooctatetrathiophene Aryl substitution Pentamer Synthesis Crystal structure Theoretical calculation |
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