A Self-Assembled Rectangular Host with Terpyridine-Platinum(II) Moieties That Binds Unsubstituted Pentacene in Solution

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• 作者：Yusuke Yamaki ; Takashi Nakamura ; Sayuri Suzuki ; Masaki Yamamura ; Mao Minoura and Tatsuya Nabeshima
• 关键词：Supramolecular chemistry ; Host&ndash ; guest systems ; Macrocycles ; Pi interactions ; Acenes
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：2016
• 期：9
• 页码：1678-1683
• 全文大小：996K
• ISSN：1099-0690

文摘

Pentacene has attracted much attention as an organic electric material, but it often suffers from its very low solubility. We now report self-assembled rectangular host 1⁸⁺ that has two pairs of terpyridine–Pt^II moieties aligned parallel to each other and connected by diyne linkers. The host encapsulated unsubstituted pentacene (2) with a remarkably strong binding constant of K_a ≈ 10⁷ M^–1 and solubilized it in acetonitrile up to the millimolar level. For smaller acenes (i.e., naphthalene to tetracene), a planar arrangement of two molecules inside the cavity was achieved. These results made it possible to analyze the acenes in the solution phase and provided a way to align the guests by a solution-processing method as a possible application, and thus, they contribute to fundamental physical organic chemistry as well as organic electronics.