We present the design of an anthracenyl⎯naphthyl (ANT⎯NAPH) dyad and its application as a luminescent 4‐stage photo switch. Both segments can individually react with singlet oxygen to switch off an optical response. In their initial form the larger ANT component reacts significantly faster and thus an ANTO2⎯NAPH stage is turned on, observed by optical response of the remaining NAPH. To reduce its reactivity, ANT is substituted with two pyridine rings. This concept is first investigated and quantified on ANT and NAPH as separated molecules. Upon protonation the reaction of ANT becomes significantly slower. For the three possible pyridyl isomers this effect increases along the order meta<para<ortho. With the pyridyl nitrogen in ortho position, the reaction completely toggles from ANT to NAPH. Application of this concept on the dyad allows to turn on the ANT⎯NAPHO2 stage with optical response of the remaining ANT. The sequence of protonation‐oxygenation‐neutralization is thereby the only possible way to isolate the unfavored form ANT⎯NAPHO2. In the dyad ANT and NAPH are directly attached and their coupling constitutes a non‐oxygenated third stage, where the NAPH luminescence is quenched and ANT luminescence is enhanced. Reaction of both NAPH and ANT to ANTO2⎯NAPHO2 constitutes the fourth dark stage.

中文翻译：

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切换蒽和萘之间的氧亲和力


我们提出了蒽基⎯萘基（ANT⎯NAPH）二元组的设计及其作为发光4级光电开关的应用。两个片段都可以单独与单线态氧反应以关闭光学响应。在其初始形式中，较大的 ANT 组件反应速度明显更快，因此 ANTO2⎯NAPH 阶段被打开，通过剩余 NAPH 的光学响应观察到。为了降低其反应性，ANT 被两个吡啶环取代。这个概念首先在 ANT 和 NAPH 作为分离的分子上进行研究和量化。质子化后，ANT 的反应明显变慢。对于三种可能的吡啶基异构体，这种效应按照间位<对位<邻位的顺序增加。当吡啶基氮处于邻位时，反应完全从 ANT 切换到 NAPH。在二元体上应用这一概念可以打开 ANT⎯NAPHO2 级，并具有剩余 ANT 的光学响应。因此，质子化-氧合-中和的顺序是分离不利形式 ANT⎯NAPHO2 的唯一可能方法。在二元体中，ANT 和 NAPH 直接连接，它们的耦合构成非氧化的第三阶段，其中 NAPH 发光被猝灭，ANT 发光增强。 NAPH 和 ANT 与 ANTO2⎯NAPHO2 的反应构成了第四个黑暗阶段。