Biesen Lukas, Müller Thomas J J
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225, Düsseldorf, Germany.
Chemistry. 2023 Nov 16;29(64):e202302067. doi: 10.1002/chem.202302067. Epub 2023 Oct 16.
Aroyl-S,N-ketene acetals represent a peculiar class of heterocyclic merocyanines, compounds bearing pronounced and rather short dipoles with great push-pull characteristics that define their rich properties. They are accessible via a wide array of synthetic concepts and procedures, ranging from addition-elimination and condensation procedures up to rearrangement and metal-mediated reactions. With our work from 2020, aroyl-S,N-ketene acetals have been identified as powerful and promising dyes with pronounced and vastly tunable solid-state emission and aggregation-induced emission properties. One characteristic trademark of this class of dye molecules is the level of control that could be exerted, and which was thoroughly explored. Based on these results, the field was opened to extend the system to bi- and multichromophoric systems by the full toolkit of synthetic organic chemistry thus giving access to even more exciting properties and manifolded substance libraries capitalizing on the AIE properties. This review aims at outlining the reaction-based principles that allow for a swift and facile access to aroyl-S,N-ketene acetals, their methodical and structural evolution and the plethora of fluorescence and aggregation properties.
芳酰基-S，N-烯酮缩醛代表了一类特殊的杂环部花青，这类化合物带有明显且较短的偶极子，具有很强的推-拉特性，这决定了它们丰富的性质。它们可以通过多种合成理念和方法获得，从加成-消除和缩合方法到重排和金属介导的反应。基于我们2020年的工作，芳酰基-S，N-烯酮缩醛已被确定为具有强大且极具可调性的固态发射和聚集诱导发光特性的有前景的染料。这类染料分子的一个显著特征是能够施加的控制水平，并且对此进行了深入探索。基于这些结果，通过合成有机化学的全套工具将该体系扩展到双发色和多发色体系的领域得以开启，从而能够利用聚集诱导发光特性获得更令人兴奋的性质和多样的物质库。本综述旨在概述基于反应的原理，这些原理能够快速且简便地获得芳酰基-S，N-烯酮缩醛、它们的方法学和结构演变以及大量的荧光和聚集性质。
