TY - JOUR
T1 - Formation of trans-Poly(thienylenevinylene) Thin Films by Solid-State Thermal Isomerization
AU - Wakioka, Masayuki
AU - Yamashita, Natsumi
AU - Mori, Hiroki
AU - Murdey, Richard
AU - Shimoaka, Takafumi
AU - Shioya, Nobutaka
AU - Wakamiya, Atsushi
AU - Nishihara, Yasushi
AU - Hasegawa, Takeshi
AU - Ozawa, Fumiyuki
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant numbers JP17H03055, JP15K17855, JP17K05883, and JST ACT-C program. Two-dimensional GIXD experiments were performed on beamline BL46XU of SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal 2018A1584, 2018B1617, 2019B1843, and 2020A1742). The authors are grateful to Drs. K. Tajima (RIKEN), M. Saito (Hiroshima University), and T. Koganezawa (JASRI) for their assistance in the measurement of 2D GIXD images. The NMR measurements (600 MHz spectrometers) were supported by the Joint Usage/Research Center (JURC) at ICR, Kyoto University. The computation time for the DFT calculations was provided by the Super Computer System, ICR, Kyoto University.
Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.
PY - 2021/7/27
Y1 - 2021/7/27
N2 - Cis-to-trans isomerization of poly(thienylenevinylene) is found to be a viable fabrication method for semiconducting trans-poly(thienylenevinylene) (trans-P1) thin films. Specifically, thin films of trans-P1, an alternating copolymer containing isoindigo and (E)-1,2-dithienylethene units, which are well known as an excellent p-type semiconductor, were prepared by thermally annealing thin films of the cis-poly(thienylenevinylene) (cis-P1) isomer (92% cis) at 240 °C for 30 min. The hole mobility of the isomerized films is comparable to that of films prepared from spin-coated solutions of the trans-isomer. Taking advantage of the greater solubility of the cis-isomer, it was possible to replace the toxic halogenated solvents normally needed for the dissolution of trans-P1 with the environmentally friendly 2-MeTHF. Solid-state cis-to-trans isomerization is therefore a potentially attractive fabrication option for the commercial development of sustainable, printable electronics.
AB - Cis-to-trans isomerization of poly(thienylenevinylene) is found to be a viable fabrication method for semiconducting trans-poly(thienylenevinylene) (trans-P1) thin films. Specifically, thin films of trans-P1, an alternating copolymer containing isoindigo and (E)-1,2-dithienylethene units, which are well known as an excellent p-type semiconductor, were prepared by thermally annealing thin films of the cis-poly(thienylenevinylene) (cis-P1) isomer (92% cis) at 240 °C for 30 min. The hole mobility of the isomerized films is comparable to that of films prepared from spin-coated solutions of the trans-isomer. Taking advantage of the greater solubility of the cis-isomer, it was possible to replace the toxic halogenated solvents normally needed for the dissolution of trans-P1 with the environmentally friendly 2-MeTHF. Solid-state cis-to-trans isomerization is therefore a potentially attractive fabrication option for the commercial development of sustainable, printable electronics.
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U2 - 10.1021/acs.chemmater.1c01016
DO - 10.1021/acs.chemmater.1c01016
M3 - Article
AN - SCOPUS:85111232233
SN - 0897-4756
VL - 33
SP - 5631
EP - 5638
JO - Chemistry of Materials
JF - Chemistry of Materials
IS - 14
ER -