5,11-Diazadibenzo[hi,qr]tetracene: Synthesis,Properties, and Reactivity toward Nucleophilic Reagents |
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| Authors: | Dr Keisuke Fujimoto Satoshi Takimoto Shota Masuda Dr Toshiyasu Inuzuka Kazutaka Sanada Prof?Dr Masami Sakamoto Prof?Dr Masaki Takahashi |
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| Institution: | 1. Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu, 432-8561 Japan;2. Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu, 501-1193 Japan;3. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522 Japan |
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| Abstract: | 5,11-Diazadibenzohi,qr]tetracene was synthesized as a new nitrogen-substituted polycyclic heteroaromatic compound by Pd-catalyzed cycloisomerization of an alkyne precursor followed by oxidative cyclization with bis(trifluoroacetoxy)iodobenzene. The substitution of imine-type nitrogen atoms significantly enhanced its electron-accepting character and facilitated the direct nucleophilic addition of arylamines under strongly basic conditions to afford the desired amino-substituted products. The introduction of amino groups induced a remarkable red-shift in their absorption spectra; the tetrasubstituted product exhibited intense near-infrared absorbing property. Furthermore, the π-electronic system, which includes a redox-active 1,4-diazabutadiene moiety, underwent reversible interconversion to its corresponding reduced form upon reduction with NaBH4 and aerobic oxidation. |
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| Keywords: | heteroacenes NIR-absorption oxidative nucleophilic substitution of hydrogen polycyclic heteroaromatics redox activity |
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