TY - JOUR
T1 - Drastic Effects of Fluorination on Backbone Conformation of Head-to-Head Bithiophene-Based Polymer Semiconductors
AU - Liao, Qiaogan
AU - Wang, Yulun
AU - Uddin, Mohammad Afsar
AU - Chen, Jianhua
AU - Guo, Han
AU - Shi, Shengbin
AU - Wang, Yang
AU - Woo, Han Young
AU - Guo, Xugang
N1 - Funding Information:
X.G. thanks NSFC (21774055 and 51573076), Shenzhen Peacock Plan (KQTD20140630110339343), Shenzhen Basic Research Fund (JCYJ20160530185244662), Shenzhen Key Lab funding (ZDSYS201505291525382), the Guangdong Natural Science Foundation (2015A030313900), and the South University of Science and Technology of China (FRG-SUSTC1501A-72). M.A.U. and H.Y.W. are grateful to the financial support from the NRF of Korea (2016M1A2A2940911 and 20100020209).
Publisher Copyright:
Copyright © 2018 American Chemical Society.
PY - 2018/5/15
Y1 - 2018/5/15
N2 - This study shows that the backbone conformation of head-to-head type 3,3′-dialkyl-2,2′-bithiophene can be tuned via fluorination of the neighboring benzothiadiazole (BTz). Without fluorination, the polymer backbone is highly twisted, whereas difluorination of BTz produced a coplanar backbone. Monofluorination of BTz yielded a tunable polymer backbone conformation depending on the film annealing temperature. In organic thin-film transistors, the polymer with the head-to-head linkages showed a remarkable hole mobility of >0.5 cm2 V-1 s-1 upon attaining a planar backbone. Thus, the head-to-head linkage does not necessarily lead to backbone nonplanarity, and achieving planar conformation of 3,3′-dialkyl-2,2′-bithiophene has profound implications in materials design for organic semiconducting devices, yielding good solubility, reduced materials synthetic steps, and improved opto-electrical properties.
AB - This study shows that the backbone conformation of head-to-head type 3,3′-dialkyl-2,2′-bithiophene can be tuned via fluorination of the neighboring benzothiadiazole (BTz). Without fluorination, the polymer backbone is highly twisted, whereas difluorination of BTz produced a coplanar backbone. Monofluorination of BTz yielded a tunable polymer backbone conformation depending on the film annealing temperature. In organic thin-film transistors, the polymer with the head-to-head linkages showed a remarkable hole mobility of >0.5 cm2 V-1 s-1 upon attaining a planar backbone. Thus, the head-to-head linkage does not necessarily lead to backbone nonplanarity, and achieving planar conformation of 3,3′-dialkyl-2,2′-bithiophene has profound implications in materials design for organic semiconducting devices, yielding good solubility, reduced materials synthetic steps, and improved opto-electrical properties.
UR - http://www.scopus.com/inward/record.url?scp=85047020001&partnerID=8YFLogxK
U2 - 10.1021/acsmacrolett.8b00032
DO - 10.1021/acsmacrolett.8b00032
M3 - Article
C2 - 35632924
AN - SCOPUS:85047020001
SN - 2161-1653
VL - 7
SP - 519
EP - 524
JO - ACS Macro Letters
JF - ACS Macro Letters
IS - 5
ER -