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12 Jul 23:23

Versatile Room-Temperature-Phosphorescent Materials Prepared from N-Substituted Naphthalimides: Emission Enhancement and Chemical Conjugation

by Xiaofeng Chen, Cheng Xu, Tao Wang, Cao Zhou, Jiajun Du, Zhongping Wang, Hangxun Xu, Tongqing Xie, Guoqiang Bi, Jun Jiang, Xuepeng Zhang, James N. Demas, Carl O. Trindle, Yi Luo, Guoqing Zhang

Abstract

Purely organic materials with room-temperature phosphorescence (RTP) are currently under intense investigation because of their potential applications in sensing, imaging, and displaying. Inspired by certain organometallic systems, where ligand-localized phosphorescence (3π-π*) is mediated by ligand-to-metal or metal-to-ligand charge transfer (CT) states, we now show that donor-to-acceptor CT states from the same organic molecule can also mediate π-localized RTP. In the model system of N-substituted naphthalimides (NNIs), the relatively large energy gap between the NNI-localized 1π-π* and 3π-π* states of the aromatic ring can be bridged by intramolecular CT states when the NNI is chemically modified with an electron donor. These NNI-based RTP materials can be easily conjugated to both synthetic and natural macromolecules, which can be used for RTP microscopy.

Thumbnail image of graphical abstract

Purely organic: N-Substituted naphthalimides (NNIs) are purely organic materials that may show room-temperature phosphorescence (RTP). The relatively large energy gap between the NNI-localized 1π-π* and 3π-π* states can be bridged by intramolecular charge transfer (CT) states when the NNI is chemically modified with an electron donor.

05 Mar 06:06

Tuning ESIPT fluorophores into dual emitters

Chem. Sci., 2016, 7,3763-3774
DOI: 10.1039/C5SC04826E, Edge Article
Open Access Open Access
Cloe Azarias, Simon Budzak, Adele D. Laurent, Gilles Ulrich, Denis Jacquemin
Using first-principle approaches, we show how ESIPT can be controlled by fine-tuning of substituents, hence leading to new dual emitters.
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