Development of new triggering system in solid state for unprecedented topochemiluminescence with high efficiency

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410056
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kanagawa University
• Principal Investigator: WATANABE Nobuko 神奈川大学, 理学部, 助教 (40291744)
• Co-Investigator(Kenkyū-buntansha): MATSUMOTO Masakatsu 神奈川大学, 付置研究所, プロジェクト研究員 (10260986)
• Co-Investigator(Renkei-kenkyūsha): IJUIN Hisako 神奈川大学, 付置研究所, プロジェクト研究員 (60398948)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 化学固体発光 / ジオキセタン型発光基質 / トポロジー

Outline of Final Research Achievements

A 3-hydroxyphenyl-substituted dioxetane fused with a tetrahydrofuran ring thermally decomposes (TD) in apolar solution to give a 3-oxopropyl 3-hydroxybenzoate with the emission [Lmax = 405 nm] due to excited ketone moiety. The dioxetane gave also the keto ester by TD in crystal (TDcryst), though the light emitted was due to excited oxidobenzoate [Lmax = 464 nm] formed by CTID (CT-induced decomposition) mechanism. The unique chemiluminescent TDcryst of the dioxetane was presumably the result of hydrogen bonding (HB) formed in the crystal between a phenolic proton of a dioxetane molecule and a peroxide oxygen of another dioxetane. On the other hand, a 4-benzazolyl-3-hydroxyphenyl substituted dioxetanes underwent TDcryst to effectively give light. Furthermore, photolysis of a crystalline dioxetane bearing a 4-benzimidazolyl-3-hydroxyphenyl group at -78o gave the corresponding keto ester, the stereochemistry of which was apparently different from that of authentic one.

Free Research Field

有機光化学