Structure engineering: extending the length of azaacene derivatives through quinone bridges

Wang, Zilong1; Wang, Zongrui1; Zhou, Yecheng2; Gu, Peiyang1; Liu, Guangfeng1; Zhao, Kexiang1; Nie, Lina1; Zeng, Qingsheng1; Zhang, Jing1; Li, Yongxin3; Ganguly, Rakesh3; Aratani, Naoki4; Huang, Li2; Liu, Zheng1; Yamada, Hiroko4; Hu, Wenping5,6; Zhang, Qichun1,3

2018-04-14

10.1039/c8tc00628h

Journal of Materials Chemistry C   影响因子和分区

2050-7526

2050-7534

Increasing the length of azaacene derivatives through quinone bridges is very important because these materials could have deep LUMO energy levels and larger overlapping in the solid state, which would have great applications in organic semiconducting devices. Here, two fully characterized large quinone-fused azaacenes Hex-CO and Hept-CO prepared through a novel palladium-catalyzed coupling reaction are reported. Our research clearly proved that the quinone unit can be employed as a bridge to extend the molecular conjugation length, increase the molecular overlapping, and engineer the molecular stacking mode. Hex-CO shows lamellar 2-D -stacking modes, while Hept-CO shows 1-D -stacking and adopts a 3-D interlocked stacking mode with the adjacent molecular layers vertical to each other. With the deep LUMO energy levels (approximate to-4.27 eV), Hex-CO and Hept-CO were both demonstrated to be electron-transport layers. Their charge transport properties were investigated through OFETs and theoretical calculations. Due to the different stacking modes, Hex-CO shows a higher electron mobility of 0.22 cm(2) V-1 s(-1) than Hept-CO (7.5 x 10(-3) cm(2) V-1 s(-1)) in a single-crystal-based OFET. Our results provide a new route for structure engineering through extending the azaacene derivatives by quinone bridges, which can be of profound significance in organic electronics.

SCI ; EI

英语

其他

JSPS[JP17H03042] ; JSPS[JP16H02286] ; JSPS[JP26105004]

Materials Science ; Physics

Materials Science, Multidisciplinary ; Physics, Applied

WOS:000429529800015

ROYAL SOC CHEMISTRY

20181505000131

Electron transport properties ; Single crystals

Bridges:401.1 ; Crystalline Solids:933.1

Web of Science

1.Nanyang Technol Univ Singapore, Sch Mat Sci & Engn, Singapore 639798, Singapore
2.South Univ Sci & Technol China, Dept Phys, Shenzhen 518055, Peoples R China
3.Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 639798, Singapore
4.Nara Inst Sci & Technol, Grad Sch Mat Sci, Ikoma 6300192, Japan
5.Tianjin Univ, Sch Sci, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
6.Tianjin Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China

Wang, Zilong,Wang, Zongrui,Zhou, Yecheng,et al. Structure engineering: extending the length of azaacene derivatives through quinone bridges[J]. Journal of Materials Chemistry C,2018,6(14):3628-3633.

Wang, Zilong.,Wang, Zongrui.,Zhou, Yecheng.,Gu, Peiyang.,Liu, Guangfeng.,...&Zhang, Qichun.(2018).Structure engineering: extending the length of azaacene derivatives through quinone bridges.Journal of Materials Chemistry C,6(14),3628-3633.

Wang, Zilong,et al."Structure engineering: extending the length of azaacene derivatives through quinone bridges".Journal of Materials Chemistry C 6.14(2018):3628-3633.