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Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels–Alder Cascade Reaction
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2016-09-22 , DOI: 10.1021/jacs.6b07647 Feng Xu 1 , Kyle W Hershey 1 , Russell J Holmes 1 , Thomas R Hoye 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2016-09-22 , DOI: 10.1021/jacs.6b07647 Feng Xu 1 , Kyle W Hershey 1 , Russell J Holmes 1 , Thomas R Hoye 1
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We describe here three alkynyl substituted naphthalenes that display promising luminescence characteristics. Each compound is easily and efficiently synthesized in three steps by capitalizing on the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction in which an intermediate benzyne is captured by tetraphenylcyclopentadienone, a classical trap for benzyne itself. These compounds luminesce in the deep blue when stimulated either optically (i.e., photoluminescence in both solution and solid films) or electrically [in a light-emitting diode (LED)]. The photophysical properties are relatively insensitive to the electronic nature of the substituents (H, OMe, CO2Me) that define these otherwise identical compounds. Overall, our observations suggest that the twisted nature of the five adjacent aryl groups serves to minimize the intermolecular interaction between core naphthalene units in different sample morphologies. These compounds represent promising leads for the identification of others of value as the emissive component of organic LEDs (OLEDs).
中文翻译：
通过十六氢二烯-阿尔德级联反应制备蓝色发射芳基炔基萘衍生物
我们在这里描述了三种具有良好发光特性的炔基取代萘。通过利用六脱氢-狄尔斯-阿尔德 (HDDA) 环异构化反应，每种化合物都可以通过三个步骤轻松高效地合成，其中中间体苯炔被四苯基环戊二烯酮捕获，四苯基环戊二烯酮是苯炔本身的经典陷阱。当受到光学刺激（即溶液和固体薄膜中的光致发光）或电刺激（在发光二极管（LED）中）时，这些化合物会发出深蓝色的光。光物理性质对定义这些相同化合物的取代基（H、OMe、CO2Me）的电子性质相对不敏感。总的来说，我们的观察表明，五个相邻芳基的扭曲性质有助于最大限度地减少不同样品形态中核心萘单元之间的分子间相互作用。这些化合物为识别其他有价值的有机 LED (OLED) 发光成分提供了有前景的线索。
更新日期：2016-09-22
中文翻译：
通过十六氢二烯-阿尔德级联反应制备蓝色发射芳基炔基萘衍生物
我们在这里描述了三种具有良好发光特性的炔基取代萘。通过利用六脱氢-狄尔斯-阿尔德 (HDDA) 环异构化反应，每种化合物都可以通过三个步骤轻松高效地合成，其中中间体苯炔被四苯基环戊二烯酮捕获，四苯基环戊二烯酮是苯炔本身的经典陷阱。当受到光学刺激（即溶液和固体薄膜中的光致发光）或电刺激（在发光二极管（LED）中）时，这些化合物会发出深蓝色的光。光物理性质对定义这些相同化合物的取代基（H、OMe、CO2Me）的电子性质相对不敏感。总的来说，我们的观察表明，五个相邻芳基的扭曲性质有助于最大限度地减少不同样品形态中核心萘单元之间的分子间相互作用。这些化合物为识别其他有价值的有机 LED (OLED) 发光成分提供了有前景的线索。
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