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. 2020 Jun 15;59(25):9946-9951.
doi: 10.1002/anie.201916057. Epub 2020 Feb 4.

9,9-Dimethylxanthene Derivatives with Room-Temperature Phosphorescence: Substituent Effects and Emissive Properties

Qiuyan Liao  1 , Qihe Gao  2 , Jiaqiang Wang  1 , Yanbing Gong  1 , Qian Peng  3 , Yu Tian  4 , Yuanyuan Fan  1 , Haojie Guo  1 , Dan Ding  2 , Qianqian Li  1 , Zhen Li  1   4
Affiliations

9,9-Dimethylxanthene Derivatives with Room-Temperature Phosphorescence: Substituent Effects and Emissive Properties

Qiuyan Liao et al. Angew Chem Int Ed Engl. .

Abstract

Room-temperature phosphorescence (RTP) emitters with ultralong lifetimes are emerging as attractive targets because of their potential applications in bioimaging, security, and other areas. But their development is limited by ambiguous mechanisms and poor understanding of the correlation of the molecular structure and RTP properties. Herein, different substituents on the 9,9-dimethylxanthene core (XCO) result in compounds with RTP lifetimes ranging from 52 to 601 ms, which are tunable by intermolecular interactions and molecular configurations. XCO-PiCl shows the most persistent RTP because of its reduced steric bulk and multiple sites of the 1-chloro-2-methylpropan-2-yl (PiCl) moiety for forming intermolecular interactions in the aggregated state. The substituent effects reported provide an efficient molecular design of organic RTP materials and establishes relationships among molecular structures, intermolecular interactions, and RTP properties.

Keywords: heterocycles; molecular configurations; noncovalent interactions; phosphorescence; substituent effects.

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