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A Self‐Assembled Rectangular Host with Terpyridine–Platinum(II) Moieties That Binds Unsubstituted Pentacene in Solution
Author(s) -
Yamaki Yusuke,
Nakamura Takashi,
Suzuki Sayuri,
Yamamura Masaki,
Minoura Mao,
Nabeshima Tatsuya
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600058
Subject(s) - pentacene , chemistry , acetonitrile , tetracene , terpyridine , platinum , solubility , molecule , molecular electronics , organic electronics , methylenedioxy , combinatorial chemistry , nanotechnology , organic chemistry , metal , halogen , materials science , electrode , quantum mechanics , catalysis , thin film transistor , physics , alkyl , transistor , voltage
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 1 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.