Efficient Synthesis And Physical Properties Of Novel Tetraazaanthracene-Based Conjugated Molecules

Organicπ-conjugated molecules, such as acene and heteroacene, have aroused considerable interests. Dispite the great success ofπ-conjugated p-type materials, n-type organic materials still remain to be fully explored. Embedding electronegative N atom to form N-heteroacene is an effective way to create n-type characters. The tetraazaanthracene comprising the 1,2-diazaine moiety, which has shown advantages for achieving low-band gap semiconductors when coupled with electron-rich building blocks, has not been reported.Herein, we developed a family of novel H-shapedπ-conjugated molecules consisting of electron-poor 2,3,7,8-tetraazaanthracene core and electron-rich thiophene arms. The single crystal and optoelectronic study revealed their typical D-A conjugated structures and n-type characters. The Peripheral substitutes on the thiophene units play an important role in tuning the solid-state packing and optoelectronic properties of these molecules. The pH titration can used to modify their molecular frontier orbitals.Our preliminary results indicate that such type of N-heteroacenes can be good candidates for organic electronic devices.