TY - JOUR
T1 - Heteroalkyl-Substitution in Molecular Organic Semiconductors
T2 - Chalcogen Effect on Crystallography, Conformational Lock, and Charge Transport
AU - Afraj, Shakil N.
AU - Lin, Chia Chi
AU - Velusamy, Arulmozhi
AU - Cho, Chang Hui
AU - Liu, Hsin Yi
AU - Chen, Jianhua
AU - Lee, Gene Hsiang
AU - Fu, Jui Chen
AU - Ni, Jen Shyang
AU - Tung, Shih Huang
AU - Yau, Shuehlin
AU - Liu, Cheng Liang
AU - Chen, Ming Chou
AU - Facchetti, Antonio
N1 - Publisher Copyright:
© 2022 The Authors. Advanced Functional Materials published by Wiley-VCH GmbH.
PY - 2022/7/4
Y1 - 2022/7/4
N2 - The effect of heteroalkyl (-XR, X = Se, S, O) substitution on a series of molecular semiconductors having a 3,3′-diheteroalkyl-2,2′-bithiophene (XBT) central core is studied. Thus, the selenotetradecyl (-SeC14H29) SeBT core is investigated by end-functionalization with two dithienothiophene (DTT), thienothiophene (TT), and thiophene (T) units to give SeBTs 1–3, respectively, for molecular π-conjugation effect examination. Furthermore, the selenodecyl (-SeC10H21) and selenohexyl (-SeC6H13) SeBT cores end-capped with DTTs to give SeBTs 1B and 1C, respectively, are synthesized for understanding -SeR length effects. To address systematically the impact of the chalcogen heteroatom, the newly developed selenoalkyl SeBTs are compared with the previously reported thiotetradecyl (-SC14H29) DDTT-SBT (4) and the new tetradecyloxy (-OC14H29) DDTT-OBT (5). When fabricating organic field effect transistors by the solution-shearing method, the devices based on the tetradecylated DDTT-SeBT (1) exhibit the highest mobility up to 4.01 cm2 V−1 s−1, which is larger than those of the other SeBT compounds and both DDTT-SBT (4) (1.70 cm2 V−1 s−1) and DDTT-OBT (5) (9.32 × 10−4 cm2 V−1 s−1). These results are rationalized by a combination of crystallographic, morphological, and microstructural analysis.
AB - The effect of heteroalkyl (-XR, X = Se, S, O) substitution on a series of molecular semiconductors having a 3,3′-diheteroalkyl-2,2′-bithiophene (XBT) central core is studied. Thus, the selenotetradecyl (-SeC14H29) SeBT core is investigated by end-functionalization with two dithienothiophene (DTT), thienothiophene (TT), and thiophene (T) units to give SeBTs 1–3, respectively, for molecular π-conjugation effect examination. Furthermore, the selenodecyl (-SeC10H21) and selenohexyl (-SeC6H13) SeBT cores end-capped with DTTs to give SeBTs 1B and 1C, respectively, are synthesized for understanding -SeR length effects. To address systematically the impact of the chalcogen heteroatom, the newly developed selenoalkyl SeBTs are compared with the previously reported thiotetradecyl (-SC14H29) DDTT-SBT (4) and the new tetradecyloxy (-OC14H29) DDTT-OBT (5). When fabricating organic field effect transistors by the solution-shearing method, the devices based on the tetradecylated DDTT-SeBT (1) exhibit the highest mobility up to 4.01 cm2 V−1 s−1, which is larger than those of the other SeBT compounds and both DDTT-SBT (4) (1.70 cm2 V−1 s−1) and DDTT-OBT (5) (9.32 × 10−4 cm2 V−1 s−1). These results are rationalized by a combination of crystallographic, morphological, and microstructural analysis.
KW - chalcogen
KW - dithienothiophene
KW - high-performance
KW - organic field effect transistors
KW - selenoalkylated bithiophene
KW - solution processable
UR - http://www.scopus.com/inward/record.url?scp=85127416142&partnerID=8YFLogxK
U2 - 10.1002/adfm.202200880
DO - 10.1002/adfm.202200880
M3 - 期刊論文
AN - SCOPUS:85127416142
SN - 1616-301X
VL - 32
JO - Advanced Functional Materials
JF - Advanced Functional Materials
IS - 27
M1 - 2200880
ER -