Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative Polymerization
We report the synthesis and absorption properties of homopolymers consisting of 1,3,4,6,9b-pentaazaphenalene (5AP). Oxidative polymerization in the Scholl reaction was accomplished, and various lengths of homopolymers can be isolated. It should be noted that we scarcely observed the generation of st...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-11-01
|
| Series: | Polymers |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4360/13/22/4021 |
| _version_ | 1797508629073494016 |
|---|---|
| author | Hiroyuki Watanabe Kazuo Tanaka Yoshiki Chujo |
| author_facet | Hiroyuki Watanabe Kazuo Tanaka Yoshiki Chujo |
| author_sort | Hiroyuki Watanabe |
| collection | DOAJ |
| description | We report the synthesis and absorption properties of homopolymers consisting of 1,3,4,6,9b-pentaazaphenalene (5AP). Oxidative polymerization in the Scholl reaction was accomplished, and various lengths of homopolymers can be isolated. It should be noted that we scarcely observed the generation of structural isomers at the connecting points, which is often observed in this type of reaction. Therefore, we were able to evaluate electronic structures of the synthesized homopolymers. In addition, it was observed that absorption bands were obtained in the longer wavelength region than the monomer. The computer calculation suggests that the highest occupied molecular orbital (HOMO) energy levels could be lowered by electronic interaction through spatially-separated HOMOs of 5AP. Moreover, we can evaluate the extension of the conjugated system through the meta-substituted skeleton and distance dependency of the main-chain conjugation. |
| first_indexed | 2024-03-10T05:06:36Z |
| format | Article |
| id | doaj.art-00e58d8d49574760822f782d8dbce014 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T05:06:36Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-00e58d8d49574760822f782d8dbce0142023-11-23T01:10:33ZengMDPI AGPolymers2073-43602021-11-011322402110.3390/polym13224021Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative PolymerizationHiroyuki Watanabe0Kazuo Tanaka1Yoshiki Chujo2Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, JapanDepartment of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, JapanDepartment of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, JapanWe report the synthesis and absorption properties of homopolymers consisting of 1,3,4,6,9b-pentaazaphenalene (5AP). Oxidative polymerization in the Scholl reaction was accomplished, and various lengths of homopolymers can be isolated. It should be noted that we scarcely observed the generation of structural isomers at the connecting points, which is often observed in this type of reaction. Therefore, we were able to evaluate electronic structures of the synthesized homopolymers. In addition, it was observed that absorption bands were obtained in the longer wavelength region than the monomer. The computer calculation suggests that the highest occupied molecular orbital (HOMO) energy levels could be lowered by electronic interaction through spatially-separated HOMOs of 5AP. Moreover, we can evaluate the extension of the conjugated system through the meta-substituted skeleton and distance dependency of the main-chain conjugation.https://www.mdpi.com/2073-4360/13/22/4021near infraredazaphenalenehomopolymernarrow band gapoxidative polymerization |
| spellingShingle | Hiroyuki Watanabe Kazuo Tanaka Yoshiki Chujo Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative Polymerization Polymers near infrared azaphenalene homopolymer narrow band gap oxidative polymerization |
| title | Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative Polymerization |
| title_full | Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative Polymerization |
| title_fullStr | Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative Polymerization |
| title_full_unstemmed | Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative Polymerization |
| title_short | Development of Long Wavelength Light-Absorptive Homopolymers Based on Pentaazaphenalene by Regioselective Oxidative Polymerization |
| title_sort | development of long wavelength light absorptive homopolymers based on pentaazaphenalene by regioselective oxidative polymerization |
| topic | near infrared azaphenalene homopolymer narrow band gap oxidative polymerization |
| url | https://www.mdpi.com/2073-4360/13/22/4021 |
| work_keys_str_mv | AT hiroyukiwatanabe developmentoflongwavelengthlightabsorptivehomopolymersbasedonpentaazaphenalenebyregioselectiveoxidativepolymerization AT kazuotanaka developmentoflongwavelengthlightabsorptivehomopolymersbasedonpentaazaphenalenebyregioselectiveoxidativepolymerization AT yoshikichujo developmentoflongwavelengthlightabsorptivehomopolymersbasedonpentaazaphenalenebyregioselectiveoxidativepolymerization |