Synthesis of a meso-Tetraalkylporphycene Bearing Reactive Sites: Toward Porphycene–Polydimethylsiloxane Hybrids with Enhanced Photophysical Properties

Toshikazu Ono, Hyuga Shinjo, Daiki Koga, Yoshio Hisaeda

研究成果: Contribution to journalArticle査読

2 被引用数 (Scopus)

抄録

meso-Tetraalkyl porphycenes exhibit unique optical properties with wide potential applications. The very fact that incorporation of porphycenes into polymeric materials is rare, make this approach a particularly attractive one. In this work, meso-tetrakis(3-butenyl)porphycene bearing four terminal olefin groups is prepared via two synthetic strategies: 1) the McMurry reaction using 5,5′-diacyl-2,2′-bipyrroles as precursors and 2) the oxidative coupling of dipyrroethenes. The newly obtained porphycene has been characterized by single X-ray crystallography. A porphycene–polydimethylsiloxane hybrid film is successfully prepared by a platinum-catalyzed hydrosilylation reaction. The hybrid film can be anchored with tweezers, showing a weak red emission with a quantum yield of 0.4 % at room temperature, whose intensity drastically increases reaching a quantum yield of 6.7 % in liquid nitrogen (77 K). This report represents the first example of porphycene-containing elastomeric films for potential application in various fields.

本文言語英語
ページ(範囲)7578-7583
ページ数6
ジャーナルEuropean Journal of Organic Chemistry
2019
46
DOI
出版ステータス出版済み - 12 15 2019

All Science Journal Classification (ASJC) codes

  • 物理化学および理論化学
  • 有機化学

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