Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State

Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11419-11423. doi: 10.1002/anie.201906507. Epub 2019 Jul 12.

Abstract

Developing molecules with high emission efficiency both in solution and the solid state is still a great challenge, since most organic luminogens are either aggregation-caused quenching or aggregation-induced emission molecules. This dilemma was overcome by integrating planar and distorted structures with long alkyl side chains to achieve DAπAD type emitters. A linear diphenyl-diacetylene core and the charge transfer effect ensure considerable planarity of these molecules in the excited state, allowing strong emission in dilute solution (quantum yield up to 98.2 %). On the other hand, intermolecular interactions of two distorted cyanostilbene units restrict molecular vibration and rotation, and long alkyl chains reduce the quenching effect of the π-π stacking to the excimer, eventually leading to strong emission in the solid state (quantum yield up to 60.7 %).

Keywords: bioimaging; luminescence; molecular engineering; molecular stacking; noncovalent interactions.