Azulene-Based π-Functional Materials

Prof. Xike GAO

Azulene is a nonbenzenoid aromatic hydrocarbon with beautiful blue color and a large dipole moment. The unique chemical structure and physicochemical properties of azulene make it one of the ideal building blocks for constructing novel π-functional materials [1]. A class of azulene-based conjugated diimides have been created and used for constructing high performance n-type organic semiconductors [2]. Later on, we developed a series of 2/6-azulene-based polymers, where the dipole arrangements of 2/6-azulene units in the polymeric backbone or side chain were finely regulated, and it was found that the dipole orientation of azulene units affects the polymers’ aggregation structure and functions [3]. Some 2/6-azulene-based polymers exhibit reversible proton response properties, high acid-doped conductivity, and the ability to accelerate proton conduction [4]. Recently, we have constructed a series of azulene-fused (hetero)aromatics, which exhibit unique physicochemical properties and molecular functions [5]. We envision that azulene-based π-functional materials would play their advantages in proton conductive materials, organic electrolyte materials, novel functional polymers as well as carbon nanomaterials.

References:

[1] ChemPlusChem. 2017, 82, 945.; Acc. Chem. Res. 2021, 54, 1737.

[2] Chem. Sci. 2016, 7, 6701.; Angew. Chem. Int. Ed. 2018, 57, 1322.; Mater. Chem. Front. 2018, 2, 975.

[3] Macromolecules 2022, 55, 8074.; Macromolecules 2023, 56, 9475.; ACS Macro Lett. 2023, 12, 487.

[4] ACS Macro Lett. 2019, 8, 1360.; ACS Macro Lett. 2022, 11, 680.; Macromolecules 2024, 57, 7516.; unpublished results.

[5] J. Am. Chem. Soc. 2020, 142, 13598.; Angew. Chem. Int. Ed. 2022, 61, e202201494.; Angew. Chem. Int. Ed. 2024, 63, e202400372.; unpublished results.