Synthesis, Optical Properties, and Crystal Structure of 1,4-Dipropyltetracene
Synthesis, Optical Properties, and Crystal Structure of 1,4-Dipropyltetracene
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DOI：
10.1002/ejoc.201000112
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发表时间：
2010-05
影响因子：
2.8
通讯作者：
C. Kitamura;C. Matsumoto;A. Yoneda;Takashi Kobayashi;H. Naito;Toshiki Komatsu
中科院分区：
文献类型：
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作者：
C. Kitamura;C. Matsumoto;A. Yoneda;Takashi Kobayashi;H. Naito;Toshiki Komatsu
我们合成了200毫克规模的1，4-二丙基并四苯，其中的关键步骤涉及原位生成的烷基取代的邻醌二甲烷与1，4-萘醌之间的Diels-Alder反应。获得的产物为橙子固体，其可溶于包括己烷的有机溶剂中。该产物在溶液中的光学性质与其它1，4，7，10-四烷基并四苯的光学性质无显著差异。与1，4，7，10-四丙基并四苯相比，固体吸收光谱和荧光光谱均发生了20-30 nm的蓝移。X射线衍射分析表明，两个丙基与并四苯环共面，沿堆积方向没有沿着π重叠，分子形成人字形结构。发现外围烷基链对于控制固态中的分子堆积和光学性质是重要的。
We synthesized 1,4-dipropyltetracene on a 200-mg scale, the key step of which involved a Diels-Alder reaction between alkyl-substituted o-quinodimethane, generated in situ, and 1,4-naphthoquinone. The product was obtained as an orange solid, which was soluble in organic solvents including hexane. The optical properties of the product in solution showed no marked differences from those of other 1,4,7,10-tetraalkyltetracenes. Solid-state absorption and fluorescence spectra exhibited 20-30 nm blueshifts compared with those of 1,4,7,10-tetrapropyltetracene. X-ray analysis revealed that two propyl groups were coplanar with the tetracene ring, that there was no π overlap along the stacking direction, and that the molecules formed a herringbone structure. The peripheral alkyl chains were found to be important for controlling the molecular packing and optical properties in the solid state.