Relief of excited-state antiaromaticity enables the smallest red emitter

Heechan Kim, Woojin Park, Younghun Kim, Michael Filatov (), Cheol Ho Choi () and Dongwhan Lee ()
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Heechan Kim: Seoul National University
Woojin Park: Kyungpook National University
Younghun Kim: Seoul National University
Michael Filatov: Kyungpook National University
Cheol Ho Choi: Kyungpook National University
Dongwhan Lee: Seoul National University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract It is commonly accepted that a large π-conjugated system is necessary to realize low-energy electronic transitions. Contrary to this prevailing notion, we present a new class of light-emitters utilizing a simple benzene core. Among different isomeric forms of diacetylphenylenediamine (DAPA), o- and p-DAPA are fluorescent, whereas m-DAPA is not. Remarkably, p-DAPA is the lightest (FW = 192) molecule displaying red emission. A systematic modification of the DAPA system allows the construction of a library of emitters covering the entire visible color spectrum. Theoretical analysis shows that their large Stokes shifts originate from the relief of excited-state antiaromaticity, rather than the typically assumed intramolecular charge transfer or proton transfer. A delicate interplay of the excited-state antiaromaticity and hydrogen bonding defines the photophysics of this new class of single benzene fluorophores. The formulated molecular design rules suggest that an extended π-conjugation is no longer a prerequisite for a long-wavelength light emission.

Date: 2021
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DOI: 10.1038/s41467-021-25677-2

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