Pyrene-1, 5, 6, 10-tetracarboxyl diimide: a new building block for high-performance electron-transporting polymers. Issue 24 (8th June 2021)

• Record Type: Journal Article
• Authors: Li, Yao; Yao, Zefan; Xie, Jiajun; Han, Han; Yang, Guantao; Bai, Xudong; Pei, Jian; Zhao, Dahui
• Is Part Of: Journal of materials chemistry. Volume 9:Issue 24(2021)
• Page Start: 7599
• Page End: 7606
• Publication Date: 2021-06-08
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Optical materials -- Research -- Periodicals; Electronics -- Materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/d1tc01729b
• Languages: English
• ISSNs: 2050-7526

Abstract

Abstract : A new polycyclic aromatic diimide of pyrene (PyDI ) bearing six-membered-ring dicarboximide is synthesized. Its conjugated polymer PyDI-TT displays an electron mobility of 0.34 cm 2 V −1 s −1, demonstrating PyDI to be an excellent building block for high-performance electron-transporting materials. Abstract : Both naphthalene and perylene derivatives bearing six-membered-ring dicarboximide groups are proven valuable modules for preparing organic electron-transporting semiconductors. However, obtaining their analogue with pyrene appeared challenging, as all previous endeavors resulted in 5- instead of 6-membered dicarboximide rings. Here, we report the first successful synthesis of pyrene-1, 5, 6, 10-tetracarboxyl diimide (PyDI ), a centro-symmetric structure comprising two 6-membered dicarboximide groups. Moreover, this molecule undergoes regioselective dihalogenation to afford a 3, 8-dibromo-substituted derivative, which may conveniently be incorporated into conjugated polymers via cross-coupling with suitable comonomers. Two representative conjugated polymers, PyDI-T and PyDI-TT, are thus prepared, composed of alternating PyDI and thiophene or bithiophene units. OFETs are then fabricated using these polymers under solution-processing conditions. An optimal electron mobility of 0.335 cm 2 V −1 s −1 is achieved by PyDI-TT, which clearly demonstrates the potential of 1, 5, 6, 10-PyDI as a potent building block for developing new high-performance electronic-transporting materials.