Synthesis ( IF 2.2 ) Pub Date : 2018-06-06 , DOI: 10.1055/s-0037-1610128 Norbert Mitzel 1 , Philipp Niermeier 1 , Jan-Hendrik Lamm 1 , Marvin Linnemannstöns 1 , Beate Neumann 1 , Hans-Georg Stammler 1
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‡ These authors contributed equally to this work.
Abstract
Starting from 10-bromo-1,8-dichloroanthracene, a series of 1,8-dichlorinated anthracene derivatives, flexibly bridged in position 10 by –Me2Si– and –Me2Si–(CH2) n –SiMe2– linker units, were synthesised. The linked anthracenes were generated by converting (1,8-dichloroanthracen-10-yl)lithium with chlorosilanes in salt-elimination reactions. The bichromophors were tested in UV light induced photo reactions. None of the new compounds yielded any intra- or intermolecular photoproduct. All α,ω-(dimethylsilyl)alkane-linked bisanthracenes decomposed to give 1,8-dichloro-9-hydroxyanthracen-10(9H)-one in the presence of oxygen. A completely different behaviour was shown by the bisanthracenyldimethylsilane, undergoing a 9,10:3′,4′-photocyclomerisation reaction. The new compounds were characterised by NMR spectroscopy, mass spectrometry and in most cases by X-ray diffraction studies.
Starting from 10-bromo-1,8-dichloroanthracene, a series of 1,8-dichlorinated anthracene derivatives, flexibly bridged in position 10 by –Me2Si– and –Me2Si–(CH2) n –SiMe2– linker units, were synthesised. The linked anthracenes were generated by converting (1,8-dichloroanthracen-10-yl)lithium with chlorosilanes in salt-elimination reactions. The bichromophors were tested in UV light induced photo reactions. None of the new compounds yielded any intra- or intermolecular photoproduct. All α,ω-(dimethylsilyl)alkane-linked bisanthracenes decomposed to give 1,8-dichloro-9-hydroxyanthracen-10(9H)-one in the presence of oxygen. A completely different behaviour was shown by the bisanthracenyldimethylsilane, undergoing a 9,10:3′,4′-photocyclomerisation reaction. The new compounds were characterised by NMR spectroscopy, mass spectrometry and in most cases by X-ray diffraction studies.
中文翻译：
α，ω-双-[（1,8-二氯蒽-10-基）二甲基甲硅烷基]烷烃的合成，固态结构和光化学
‡这些作者对这项工作做出了同等的贡献。
抽象的
从10-溴1,8-二氯蒽开始，一系列1,8-二氯蒽衍生物，通过–Me 2 Si–和–Me 2 Si–（CH 2）n –SiMe 2 –接头灵活地桥接在位置10单位，被合成。通过在盐消除反应中用氯硅烷转化（1,8-二氯蒽-10-基）锂来生成连接的蒽。在紫外线诱导的光反应中测试了双色团。这些新化合物均未产生任何分子内或分子间的光产物。所有α，ω-（二甲基甲硅烷基）烷烃连接的双蒽被分解，得到1,8-二氯-9-羟基蒽-10（9 H ）-在氧气存在下的一个。双蒽基二甲基硅烷显示出完全不同的行为，它经历了9,10：3'，4'-光环化反应。这些新化合物通过NMR光谱，质谱和大多数情况下的X射线衍射研究进行了表征。
从10-溴1,8-二氯蒽开始，一系列1,8-二氯蒽衍生物，通过–Me 2 Si–和–Me 2 Si–（CH 2）n –SiMe 2 –接头灵活地桥接在位置10单位，被合成。通过在盐消除反应中用氯硅烷转化（1,8-二氯蒽-10-基）锂来生成连接的蒽。在紫外线诱导的光反应中测试了双色团。这些新化合物均未产生任何分子内或分子间的光产物。所有α，ω-（二甲基甲硅烷基）烷烃连接的双蒽被分解，得到1,8-二氯-9-羟基蒽-10（9 H ）-在氧气存在下的一个。双蒽基二甲基硅烷显示出完全不同的行为，它经历了9,10：3'，4'-光环化反应。这些新化合物通过NMR光谱，质谱和大多数情况下的X射线衍射研究进行了表征。
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