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Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

机译:溶液化学法高效制备[60]富勒烯和蒽单加合物及其固态热分解

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The efficient preparation of monoadducts of [60]fullerene and seven anthracenes(anthracene,1-methylan-thracene,2-methylanthracene,9-meth-ylanthracene,9,10-dimethylanthracene,2,3,6,7-tetramethylanthracene,and 2,6-di-tert-butylanthracene)by cycloaddi-tion in solution is described.The Seven mono-adducts of [60]fullerene and the anthracenes were characterized spectro-scopically and were obtained in good yields as crystalline solids.The mono-adducts of [60]fullerene and anthracene,1-methylanthracene,2-methylanthra-cene and 9,10-dimethylanthracene crys-tallized directly from the reaction mix-ture.The thermolytic decomposition at 180 deg C of the crystalline monoadducts of [60]fullerene and anthracene,1-methy1-anthracene,9-methylanthracene and 9,10-dimethylanthracene all gave rise to the specific formation of a roughly 1:1 mixture of [60] fullerene and the corresponding antipodal bisadducts ("trans-1"-bisadducts)of [60]fullerene and the .In contras,the crystalline monoadducts of [60]fullerene and the anthracene derivatives 2-meth-ylanthracene,2,3,6,7-tetramethylanthra-cene and 2.6-di tert butylanthracene all decomposed to [60]fullerene and an thracenes(without detectable formation of bisadducts)upon heating in the solid state to temperatures of 180 to 240 deg C.The formation of the antipodal bisad-ducts from thermolkytic decomposition of crystalline samples of the monoad-ducts was rationalized by topochemical control.
机译:有效制备[60]富勒烯和七个蒽的单加合物(蒽,1-甲基蒽,2-甲基蒽,9-甲基蒽,9,10-二甲基蒽,2,3,6,7-四甲基蒽和2描述了在溶液中通过环加成反应生成的(6-二叔丁基蒽)。用光谱法表征了[60]富勒烯和蒽的七个单加合物,并以良好的收率得到了结晶固体。 [60]富勒烯和蒽,1-甲基蒽,2-甲基蒽和9,10-二甲基蒽的混合物直接从反应混合物中结晶。[60]富勒烯的结晶单加合物在180℃下热分解蒽,1-甲基1-蒽,9-甲基蒽和9,10-二甲基蒽都引起[60]富勒烯与相应的对映体双加合物(“ trans-1”-双加合物)的约1:1混合物的特定形成。 )和[60]富勒烯的芳烃。相反,[60]富勒烯的晶体单加合物并在固态加热下,将蒽衍生物2-甲基-蒽,2,3,6,7-四甲基蒽和2.6-二叔丁基蒽分解为[60]富勒烯和蒽(没有检测到双加合物的形成)。最高温度为180到240摄氏度。通过拓扑化学控制合理化了单链成因的结晶样品的热解分解形成的对映双链成因。

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