Rigid Tether Directed Regioselective Synthesis and Crystallographic Characterization of Labile 1,2,3,4‐Bis(triazolino)[60]fullerene and Its Thermolized Derivatives |
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Authors: | Dr Muqing Chen Dr Lipiao Bao Prof Ping Peng Dr Shushu Zheng Prof Yunpeng Xie Prof Xing Lu |
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Institution: | 1. State Key Laboratory of Materials Processing and Die & Mould Technology, School of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan, P.R. China;2. Department of Materials Physics, School of Physics and Mechanical & Electronical Engineering, Hubei University of Education, Wuhan, P.R. China |
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Abstract: | Labile bis‐triazoline adducts of C60 are supposed to be the precursors of bis‐azafulleroids, but the formation mechanism is still unclear because of the incomplete isolation of the thermolized products and the lack of X‐ray structures. A rigid‐tethered reagent 1,2‐bis(azidomethyl)benzene ( 1 ) was used to regioselectively synthesize the labile 1,2,3,4‐bis(triazolino)60]‐fullerene ( 2 ), the structure of which was determined by single‐crystal X‐ray crystallography. Further thermolysis of 2 produces four products (3 a – 3 d ), which were all characterized by X‐ray crystallography. Although 3 a and 3 b have traditional bis‐azafulleroid structures, as proposed previously, 3 c and 3 d show unprecedented structures with either the coexistence of 5,6]‐open and 6,6]‐closed patterns or an oxidized structure with an 11‐membered ring on the cage. A thermolysis mechanism is proposed to clarify long‐term confusion about the transformation process from bis‐triazoline adducts to bis‐azafulleroids of C60. |
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Keywords: | azides bis-azafulleroids bis-triazoline fullerenes structure elucidation |
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