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    Why Do Simple Molecules with “Isolated” Phenyl Rings Emit Visible Light?
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    † Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
    ‡ Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Institute for Advanced Study, Institute of Molecular Functional Materials, State Key Laboratory of Molecular Neuroscience, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
    § Guangdong Provincial Key Laboratory of Brain Science, Disease and Drug Development, HKUST Shenzhen Research Institute, No. 9 Yuexing First RD, South Area, Hi-tech Park Nanshan, Shenzhen 518057, China
    ∥ Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China
    ⊥ Department of Physics, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
    # National Center for Nanoscience and Technology, Beijing 100190, China
    *[email protected]
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    Cite this: J. Am. Chem. Soc. 2017, 139, 45, 16264–16272
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    https://doi.org/10.1021/jacs.7b08592
    Published October 24, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    π-Bonds connected with aromatic rings were generally believed as the standard structures for constructing highly efficient fluorophores. Materials without these typical structures, however, exhibited only low fluorescence quantum yields and emitted in the ultraviolet spectral region. In this work, three molecules, namely bis(2,4,5-trimethylphenyl)methane, 1,1,2,2-tetrakis(2,4,5-trimethylphenyl)ethane, and 1,1,2,2-tetraphenylethane, with nonconjugated structures and isolated phenyl rings were synthesized and their photophysical properties were systematically investigated. Interestingly, the emission spectra of these three molecules could be well extended to 600 nm with high solid-state quantum yields of up to 70%. Experimental and theoretical analyses proved that intramolecular through-space conjugation between the “isolated” phenyl rings played an important role for this abnormal phenomenon.

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    Cite this: J. Am. Chem. Soc. 2017, 139, 45, 16264–16272
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