Biazulene diimides: a new building block for organic electronic materials† †Electronic supplementary information (ESI) available. CCDC 1483780. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc02504h Click here for additional data file.

Azulene, a 10-p-electron isomer of naphthalene, is a nonbenzenoid bicyclic aromatic hydrocarbon with a beautiful blue color and a large dipole moment. We present here the first class of azulene-based aromatic diimides, 2,20-biazulene-1,10,3,30-tetracarboxylic diimides (BAzDIs), which comprise a 2,20biazulene moiety and two seven-membered imide groups. DFT calculations, thermal, optical and electrochemical properties of two BAzDI derivatives as well as single crystal analysis and the charge transport behavior were studied. The results demonstrate that BAzDIs have unique photophysical properties and are promising for organic electronic materials.