Parallel synthesis of donor-acceptor π-conjugated polymers by post-element transformation of organotitanium polymer

Yoshimasa Matsumuraa Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPAN;b Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, JAPAN

https://orcid.org/0000-0001-9127-862X

Alvin Tanudjajaa Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPAN

Mizuki Fukushimaa Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPAN

Makoto Higuchia Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPAN

Shin Oginoa Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPAN

Makoto Ishidoshiroc Graduate School of Science and Technology, Kyoto Institute of Technology, Kyoto, JAPAN

Yasuyuki Iriec Graduate School of Science and Technology, Kyoto Institute of Technology, Kyoto, JAPAN

Hiroaki Imotoc Graduate School of Science and Technology, Kyoto Institute of Technology, Kyoto, JAPAN

https://orcid.org/0000-0003-1495-3059

Kensuke Nakac Graduate School of Science and Technology, Kyoto Institute of Technology, Kyoto, JAPAN

https://orcid.org/0000-0002-4516-6296

Ryoyu Hifumia Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPAN

Shinsuke Inagia Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPAN

https://orcid.org/0000-0002-9867-1210

Ikuyoshi Tomitaa Department of Chemical Science and Engineering, Graduate School of Materials and Chemical Technology, Tokyo Institute of Technology, Yokohama, JAPANCorrespondence[email protected]

https://orcid.org/0000-0003-3995-5528

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ABSTRACT

The donor-acceptor type π-conjugated polymers having heterole units were prepared by the reaction of a regioregular organometallic polymer having both reactive titanacyclopentadiene and electron-donor thiophene-2,5-diyl units in the main chain with electrophiles such as diphenyltin dichloride, dichlorophenylphosphine, and diiodophenylarsine. For example, a polymer having electron-accepting phosphole unit was obtained in 54% yield whose number-average molecular weight (M_n) and molecular weight distribution (M_w/M_n) were estimated as 3,000 and 1.9, respectively. The obtained polymer exhibits a high highest occupied molecular orbital (HOMO) and low lowest unoccupied molecular orbital (LUMO) energy levels (−5.13 eV and −3.25 eV, respectively) due to the electron-donating thiophene and electron-accepting phosphole units. Reflecting upon the alternating structure of thiophene and phosphole, the polymer exhibits a band gap energy level (E_g) of 1.78 eV which is narrower than that of a derivative of poly(thiophene) (E_g = 2.25 eV).

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Acknowledgments

This work was supported by JSPS KAKENHI Grant Number JP21H01982 and a Grant-in-Aid for Scientific Research on Innovative Areas “New Polymeric Materials Based on Element-Blocks (No.2401)” (24102007) of The Ministry of Education, Culture, Sports, Science, and Technology, Japan.

Disclosure statement

No potential conflict of interest was reported by the authors.

Supplementary material

Supplemental data for this article can be accessed online at https://doi.org/10.1080/15685551.2023.2233228.

Parallel synthesis of donor-acceptor π-conjugated polymers by post-element transformation of organotitanium polymer

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Parallel synthesis of donor-acceptor π-conjugated polymers by post-element transformation of organotitanium polymer

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