Indacenodithiazole-Ladder-Type Bridged Di(thiophene)-Difluoro-Benzothiadiazole-Conjugated Copolymers as Ambipolar Organic Field-Effect Transistors

Barł  ó;  g, Maciej; Zhang, Xianhe2; Kulai, Ihor1; Yang, Da Seul3; Sredojevic, Dusan N.1; Sil, Aritra4; Ji, Xiaozhou5; Salih, Kifah S. M.6; Bazzi, Hassan S.1,7; Bronstein, Hugo8; Fang, Lei5; Kim, Jinsang3; Marks, Tobin J.4; Guo, Xugang2; Al-Hashimi, Mohammed1

2019

10.1021/acs.chemmater.9b03525

Chemistry of Materials   影响因子和分区

15205002

1520-5002

A series of four donor-acceptor conjugated copolymers P1-P4 with linear and branched side chains based on a ladder-type indacenodithiazole (IDTz) moiety containing an electron-deficient thiazole unit are copolymerized with di-2-thienyl-2,1,3-benzothiadiazole (DTBT) and 4,7-di(thien-2-yl)-5,6-difluoro-2,1,3-benzothiadiazole (DTBTff) as building blocks. Their optical, electrochemical, and thermal properties and charge transport behavior in organic field-effect transistors (OFETs) are studied. All copolymers exhibit nearly identical features in solution with good solubility. In the solid state, P1 does not exhibit a significant shift, while P3 shows a 27 nm red shift, thus illustrating the influence of the side chain. In the case of copolymers P1 and P2 having linear side chains, there is a clear effect of fluorination on the film morphology, while it is less pronounced in the case of polymers P3 and P4 having branched side chains. All copolymers P1-P4 have similar highest occupied molecular orbitals regardless of fluorination, while fluorinated polymers P2 and P4 result in an increase in the lowest unoccupied molecular orbital. In addition, density functional theory calculations reveal that the energy levels of IDTz are down-shifted in comparison to its IDT counterpart containing an electron-rich thiophene unit. OFETs based on all copolymers exhibit ambipolar behavior; among the four copolymers, P2 having a linear dodecyl side chain exhibits remarkable transport properties with saturated hole mobility as high as 0.87 cm² V^-1 s^-1, while P3 exhibits the highest electron mobility of up to 0.50 cm² V^-1 s^-1. Our results set an interesting path to further utilize the electron-deficient thiazole block in semiconducting materials.
Copyright © 2019 American Chemical Society.

SCI ; EI

英语

其他

Qatar National Research Fund[] ; [NPRP 8-245-1-059] ; Qatar National Research Fund[]

Chemistry ; Materials Science

Chemistry, Physical ; Materials Science, Multidisciplinary

WOS:000500039100029

American Chemical Society

20194707711042

Density functional theory ; Electron energy levels ; Electrons ; Fluorination ; Halogenation ; Hole mobility ; Ladders ; Molecular orbitals ; Polymers ; Red Shift ; Thiophene

Construction Equipment:405.1 ; Semiconducting Materials:712.1 ; Semiconductor Devices and Integrated Circuits:714.2 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1 ; Polymeric Materials:815.1 ; Probability Theory:922.1

MATERIALS SCIENCE

Web of Science

1.Department of Chemistry, Texas AandM University at Qatar, P.O. Box 23874, Doha, Qatar
2.Department of Materials Science and Engineering, Southern University of Science and Technology, Shenzhen; 518055, China
3.Macromolecular Science and Engineering, University of Michigan, Ann Arbor; Michigan; 48109, United States
4.Department of Chemistry and the Materials Research Center, Northwestern University, Evanston; Illinois; 60208-3113, United States
5.Department of Chemistry, Texas AandM University, 3255 TAMU, College Station; Texas; 77845-3255, United States
6.Department of Chemistry and Earth Sciences, Qatar University, P.O. Box 2713, Doha, Qatar
7.Department of Materials Science and Engineering, Texas AandM University, 209 Reed McDonald Building, College Station; Texas; 77843-3003, United States
8.Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge; CB2 1EW, United Kingdom

Barłóg, Maciej,Zhang, Xianhe,Kulai, Ihor,et al. Indacenodithiazole-Ladder-Type Bridged Di(thiophene)-Difluoro-Benzothiadiazole-Conjugated Copolymers as Ambipolar Organic Field-Effect Transistors[J]. Chemistry of Materials,2019,31(22):9488-9496.

Barłóg, Maciej.,Zhang, Xianhe.,Kulai, Ihor.,Yang, Da Seul.,Sredojevic, Dusan N..,...&Al-Hashimi, Mohammed.(2019).Indacenodithiazole-Ladder-Type Bridged Di(thiophene)-Difluoro-Benzothiadiazole-Conjugated Copolymers as Ambipolar Organic Field-Effect Transistors.Chemistry of Materials,31(22),9488-9496.

Barłóg, Maciej,et al."Indacenodithiazole-Ladder-Type Bridged Di(thiophene)-Difluoro-Benzothiadiazole-Conjugated Copolymers as Ambipolar Organic Field-Effect Transistors".Chemistry of Materials 31.22(2019):9488-9496.