Citation: Jiaxiang Guo, Zeyi Li, Tianyu Zhang, Xinyu Tian, Yue Wang, Chuandong Dou. Thienothiophene-centered ladder-type π-systems that feature distinct quinoidal π-extension[J]. Chinese Chemical Letters, ;2024, 35(5): 109337. doi: 10.1016/j.cclet.2023.109337 shu

Thienothiophene-centered ladder-type π-systems that feature distinct quinoidal π-extension

Jiaxiang Guo ^{a, 1} ,
Zeyi Li ^{a, 1} ,
Tianyu Zhang ^a ,
Xinyu Tian ^a ,
Yue Wang ^a ,
Chuandong Dou ^{a, b, *,}

a.
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
b.
Jiangsu Engineering Laboratory of Novel Functional Polymeric Materials, Soochow University, Suzhou 215123, China

chuandong@jlu.edu.cn

Received Date: 4 September 2023
Revised Date: 17 November 2023
Accepted Date: 23 November 2023
Available Online: 25 November 2023

Figures(7)

Quinoidal π-conjugated structures, a kind of fundamental subunits for organic π-systems, may produce some intriguing optical, electronic and magnetic properties of polycyclic hydrocarbons (PHs). Herein, we report two thienothiophene-centered ladder-type polycyclic molecules (1 and 2), which possess one quinoidal thienothiophene moiety and two para-quinodimethane (p-QDM) subunits, respectively. As theoretically and experimentally studied, while 1 is a fully closed-shell molecule, 2 owns an open-shell structure along with partial contribution of tetraradical state that is induced by the resonance of p-QDM. Moreover, although 2 has a larger π-conjugated skeleton and open-shell electronic state, it exhibits larger bandgap and blue-shifted absorption. On the other hand, the reversible oxidation activity of 1 enables the preparation of its dication, and the studies on its single-crystal and aromatic structures demonstrate that its two positive charges are delocalized onto the oxygen atoms, thus achieving fully π-extended structure and near-infrared absorption. This study not only gains insight into quinoidal π-subunits, but also provides an important basis for the development of antiaromatic and open-shell π-electron materials.
- Thienothiophene,
- Quinoidal conjugation,
- Open-shell structure,
- Aromaticity,
- Photophysical properties
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