Azulene has attracted considerable attention due to its unique chemical structure and unusual properties, including a large dipole moment of 1.08 D derived from its nonalternant structure with an electron-poor seven-membered ring and an electron-rich five-membered ring, long-wavelength weak absorption (S0→S1) with narrow HOMO–LUMO energy gap, as well as abnormal fluorescence (anti-Kasha’s rule, S2→S0) resulting from its large energy gap between S1 and S2. In recent years, azulene and its derivatives have gained increasing attention due to their successful applications in organic optoelectronic devices, such as organic field-effect transistors (OFETs) and organic photovoltaics (OPVs). However, the development of azulene-based organic optoelectronic materials is hampered by the difficulty in molecule design and synthesis. Recently, we developed a class of azulene-based aromatic diimides, 2,2¢-biazulene-1,1¢,3,3¢-tetracarboxylic diimides (BAzDIs, Figure 1), which are quite different from perylene diimides (PDIs) in colour and in physicochemical properties, although the difference in the chemical formulas between BAzDIs and PDIs with the same R substituents is two extra hydrogen atoms for BAzDIs. Some latest developed BAzDI-based organic small molecular/polymeric semiconductors have shown high electron mobilities of up to 0.5 cm2 V-1 s-1 in OFETs and great potentialities in OPVs as electron acceptors. Our primary results demonstrate that BAzDIs are promising building blocks for organic optoelectronic materials.

Biazulene diimides for small molecular and polymeric semiconductors

256th National Meeting (2018)

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