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

IF 1.8 4区化学 Q3 POLYMER SCIENCE Designed Monomers and Polymers Pub Date : 2023-01-01 DOI:10.1080/15685551.2023.2233228

Yoshimasa Matsumura, Alvin Tanudjaja, Mizuki Fukushima, Makoto Higuchi, Shin Ogino, Makoto Ishidoshiro, Yasuyuki Irie, Hiroaki Imoto, Kensuke Naka, Ryoyu Hifumi, Shinsuke Inagi, Ikuyoshi Tomita

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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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有机钛聚合物元素后转化平行合成供受体π共轭聚合物。

以具有活性的钛环戊二烯和电子给体噻吩-2,5-二基为主链的区域规整型有机金属聚合物与亲电试剂如二苯基二氯化锡、二氯苯基膦和二碘苯larsine反应制备了具有杂环单元的给受体型π共轭聚合物。例如，以54%的产率获得了具有电子接受磷孔单元的聚合物，估计其数平均分子量(Mn)和分子量分布(Mw/Mn)分别为3,000和1.9。该聚合物具有较高的最高已占据分子轨道(HOMO)和较低的最低未占据分子轨道(LUMO)能级(分别为-5.13 eV和-3.25 eV)，这是由于提供电子的噻吩和接受电子的磷空穴单元。根据噻吩和磷孔的交替结构，聚合物的带隙能级(Eg)为1.78 eV，比聚噻吩衍生物的带隙能级(Eg = 2.25 eV)窄。

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来源期刊

Designed Monomers and Polymers 化学-高分子科学

CiteScore

3.30

自引率

0.00%

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审稿时长

2.1 months

期刊介绍： Designed Monomers and Polymers ( DMP) publishes prompt peer-reviewed papers and short topical reviews on all areas of macromolecular design and applications. Emphasis is placed on the preparations of new monomers, including characterization and applications. Experiments should be presented in sufficient detail (including specific observations, precautionary notes, use of new materials, techniques, and their possible problems) that they could be reproduced by any researcher wishing to repeat the work. The journal also includes macromolecular design of polymeric materials (such as polymeric biomaterials, biomedical polymers, etc.) with medical applications. DMP provides an interface between organic and polymer chemistries and aims to bridge the gap between monomer synthesis and the design of new polymers. Submssions are invited in the areas including, but not limited to: -macromolecular science, initiators, macroinitiators for macromolecular design -kinetics, mechanism and modelling aspects of polymerization -new methods of synthesis of known monomers -new monomers (must show evidence for polymerization, e.g. polycondensation, sequential combination, oxidative coupling, radiation, plasma polymerization) -functional prepolymers of various architectures such as hyperbranched polymers, telechelic polymers, macromonomers, or dendrimers -new polymeric materials with biomedical applications