title: One-Shot Double Amination of Sondheimer-Wong Diynes: Synthesis of Photoluminescent Dinaphthopentalenes.
abstract: Photoluminescent diamino-substituted dinaphthopentalenes were synthesized successfully by the treatment of in situ prepared dinaphthocyclooctadiyne with lithium amide. This reaction involves a series of transformations including the nucleophilic addition of the lithium amide to a triple bond of the cyclooctadiyne moiety, transannulation, protonation of the resulting pentalene anion, and the nucleophilic substitution of the pentalene core with the lithium amide. In this procedure, a novel double amination step plays a key role. When the diamino-substituted dinaphthopentalenes were irradiated with UV light in toluene, fluorescence was observed at around 580 nm (ΦF < 0.03).
authors.affiliation: †Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Feng
authors.initials: F
authors.lastname: Xu
authors.affiliation: †Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Lifen
authors.initials: L
authors.lastname: Peng
authors.affiliation: †Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Kenta
authors.initials: K
authors.lastname: Shinohara
authors.affiliation: †Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Takanori
authors.initials: T
authors.lastname: Nishida
authors.affiliation: ‡Department of Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Kan
authors.initials: K
authors.lastname: Wakamatsu
authors.affiliation: §Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoyo 615 8510, Japan.
authors.forename: Motoyuki
authors.initials: M
authors.lastname: Uejima
authors.affiliation: §Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoyo 615 8510, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Sato
authors.affiliation: §Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoyo 615 8510, Japan.
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Tanaka
authors.affiliation: ∥Research Institute of Natural Sciences, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Norihiko
authors.initials: N
authors.lastname: Machida
authors.affiliation: ∥Research Institute of Natural Sciences, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Haruo
authors.initials: H
authors.lastname: Akashi
authors.affiliation: †Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Orita
authors.affiliation: †Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700 0005, Japan.
authors.forename: Junzo
authors.initials: J
authors.lastname: Otera