Synthesis, Single Crystal, and Physical Properties of Asymmetrical Thiophene/Selenophene-Fused Twistacenes

• Published in: Chemistry, an Asian journal an Asian journal, 2015-12, Vol.10 (12), p.2677-2682
• Main Authors: Lv, Bo, Shen, Xingxing, Xiao, Jinchong, Duan, Jingdan, Wang, Xuefei, Yi, Yuanping
• Format: Article
• Language: English
• Subjects: Chemistry; Crystallography, X-Ray; Electrochemical Techniques; heteroacenes; Molecular Conformation; optical property; Organoselenium Compounds - chemical synthesis; Organoselenium Compounds - chemistry; Quantum Theory; self-assembly; synthesis; Thiophenes - chemical synthesis; Thiophenes - chemistry; twisted structures
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201500733

Two asymmetrical twistacenes, PyPT and PyPS, have been synthesized and characterized. Single crystal X‐ray analyses show that both of them have twisted structures with a torsion angle of 26.65° for PyPT and 26.59° for PyPS measured between plane C5‐C23‐C25 and plane C13‐C15‐C26. The thiophene/selenophene‐fused acenes emit blue fluorescence with quantum yields of 0.39 for PyPT and 0.04 for PyPS in organic solvents, whereas the all‐carbon molecule HBP emits green fluorescence. Meanwhile, PyPT and PyPS show a similar reversible oxide procedure with the onset potentials of 0.73 and 0.72 V, respectively. In addition, PyPT and PyPS can self‐assemble to form nanoparticles in a mixture of THF/H2O through re‐precipitation method. Twist and Shout: Two asymmetrical twistacenes PyPT and PyPS have been synthesized. Single crystal X‐ray analyses showed that PyPT and PyPS have twisted structures with torsion angles of 26.65° and 26.59°, respectively. Their preliminary optoelectronic properties and self‐assembly behavior were also investigated.