A Self‐Assembled Rectangular Host with Terpyridine–Platinum(II) Moieties That Binds Unsubstituted Pentacene in Solution. Issue 9 (12th February 2016)

• Record Type: Journal Article
• Authors: Yamaki, Yusuke; Nakamura, Takashi; Suzuki, Sayuri; Yamamura, Masaki; Minoura, Mao; Nabeshima, Tatsuya
• Is Part Of: European journal of organic chemistry. Issue 9(2016)
• Page Start: 1678
• Page End: 1683
• Publication Date: 2016-02-12
• Subjects: Supramolecular chemistry -- Host–guest systems -- Macrocycles -- Pi interactions -- Acenes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600058
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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 host1 8+ 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 ≈ 10 7 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. Abstract : A self‐assembled rectangular host with terpyridine–Pt II moieties encapsulates unsubstituted pentacene with a remarkably strong binding constant of K a ≈ 10 7 M –1 . Furthermore, a planar arrangement of two molecules of the smaller acenes (i.e., naphthalene to tetracene) is achieved inside the cavity.