Detection and Crystal Structure of Hydrogenated Bipentacene as an Intermediate in Thermally Induced Pentacene Oligomerization.
Detection and Crystal Structure of Hydrogenated Bipentacene as an Intermediate in Thermally Induced Pentacene Oligomerization.
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氢化双并五苯作为热诱导并五苯齐聚中间体的检测和晶体结构。
DOI：
10.1021/acs.joc.9b00671
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发表时间：
2019
期刊：
影响因子：
--
通讯作者：
Hiley CI
中科院分区：
文献类型：
--
作者：
Hiley CI
合成了6，6 ′，13，13 ′-四氢-6，6 ′-联并五苯（HBP），并对其进行了晶体学表征。在真空下将并五苯加热至300 °C持续200小时，得到了HB的淡金色晶体和含有并五苯低聚物的无定形材料，提供了并五苯优先在6，6 ′-位二聚的实验证据。继续加热HBP导致6，13-二氢化并五苯和并五苯的共晶体以及进一步的无定形并五苯低聚物。该无定形材料由具有石墨烯性质的层状碳质物质组成，如通过拉曼光谱和电子显微镜所测定的，以及作为氢化并五苯物质和并五苯低聚物（例如有机电子学中感兴趣的并五苯）的中间体的聚苯乙烯-HBP 3。
6,6′,13,13′-Tetrahydro-6,6′-bipentacene (HBP), the intermediate molecule connecting pentacene to previously observed peripentacene and extended pentacene oligomers through the formation of a carbon–carbon bond, is synthesized and crystallographically characterized. Heating pentacene to 300 °C under vacuum for 200 h results in pale golden crystals ofHBPand amorphous material containing pentacene oligomers, offering experimental evidence that pentacene preferentially dimerizes at the 6,6′-position. Continued heating ofHBPresults in co-crystals of 6,13-dihydrogenated pentacene and pentacene and further amorphous pentacene oligomers. The amorphous material consists of layered carbonaceous species with a graphenic nature, as determined by Raman spectroscopy and electron microscopy, and suggestsHBPas an intermediate to hydrogenated pentacene species and pentacene oligomers, such as peripentacene, of interest in organic electronics.