Two-electron transfer stabilized by excited-state aromatization

Jinseok Kim, Juwon Oh, Seongchul Park, Jose L. Zafra, Justin R. DeFrancisco, David Casanova (), Manho Lim (), John D. Tovar (), Juan Casado () and Dongho Kim ()
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Jinseok Kim: Yonsei University
Juwon Oh: Yonsei University
Seongchul Park: Pusan National University
Jose L. Zafra: University of Málaga, Andalucia-Tech, Campus de Teatinos s/n
Justin R. DeFrancisco: Johns Hopkins University
David Casanova: Donostia, International Physics Center (DIPC) & IKERBASQUE - Basque Foundation for Science
Manho Lim: Pusan National University
John D. Tovar: Johns Hopkins University
Juan Casado: University of Málaga, Andalucia-Tech, Campus de Teatinos s/n
Dongho Kim: Yonsei University

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract The scientific significance of excited-state aromaticity concerns with the elucidation of processes and properties in the excited states. Here, we focus on TMTQ, an oligomer composed of a central 1,6-methano[10]annulene and 5-dicyanomethyl-thiophene peripheries (acceptor-donor-acceptor system), and investigate a two-electron transfer process dominantly stabilized by an aromatization in the low-energy lying excited state. Our spectroscopic measurements quantitatively observe the shift of two π-electrons between donor and acceptors. It is revealed that this two-electron transfer process accompanies the excited-state aromatization, producing a Baird aromatic 8π core annulene in TMTQ. Biradical character on each terminal dicyanomethylene group of TMTQ allows a pseudo triplet-like configuration on the 8π core annulene with multiexcitonic nature, which stabilizes the energetically unfavorable two-charge separated state by the formation of Baird aromatic core annulene. This finding provides a comprehensive understanding of the role of excited-state aromaticity and insight to designing functional photoactive materials.

Date: 2019
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DOI: 10.1038/s41467-019-12986-w

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