Aggregation-induced enhanced fluorescence by hydrogen bonding in π-conjugated tricarbocycles with a CF2CF2-containing cyclohexa-1,3-diene skeleton
Aggregation-induced enhanced fluorescence by hydrogen bonding in π-conjugated tricarbocycles with a CF2CF2-containing cyclohexa-1,3-diene skeleton
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含有 CF2CF2 的环己-1,3-二烯骨架的 π 共轭三碳环通过氢键聚集诱导增强荧光
DOI：
10.1039/d2me00055e
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Konno Tsutomu
中科院分区：
文献类型：
--
作者：
Ohsato Haruka;Morita Masato;Yamada Shigeyuki;Agou Tomohiro;Fukumoto Hiroki;Konno Tsutomu
基于对含CF_2CF_2有机分子的理解，最近从市售的4-溴-3，3，4，4-正丁-1-烯经八步反应合成了具有含CF_2CF_2环己-1，3-二烯骨架的π-共轭三碳环化合物。近年来，固态发光分子得到了积极的发展，但高效发光体的分子设计受到限制。基于分子结构中的氟原子通过H → F氢键增强发光效率的认识，本研究的目的是阐明具有含CF2 CF2骨架的环己-1，3-二烯的π共轭三碳环作为一种新的固态发光体分子设计的适用性。π-共轭三碳环在稀溶液中显示荧光，但具有低荧光效率。然而，向四氢呋喃溶液中加入80%的水显著增加了荧光效率。在结晶状态下，三碳环化合物显示出蓝色或绿色荧光，具有非常高的荧光效率，这是由于分子间形成了C F氢键。这证明了三环π共轭分子具有聚集体诱导的发光增强特性。这些结果表明，具有含CF2 CF2环己-1，3-二烯骨架的π-共轭三碳环化合物具有良好的固态发光性能，为开发新型固态发光材料，如有机发光二极管或照明器件奠定了基础。
On the basis of the understanding of CF2CF2-containing organic molecules, π-conjugated tricarbocycles with a CF2CF2-containing cyclohexa-1,3-diene skeleton have recently been prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene in eight steps. Solid-state luminescent molecules have been actively developed in recent years, but the molecular design of efficient luminophores has been limited. Based on the knowledge that the fluorine atoms in molecular structures are responsible for the enhanced luminescence efficiency through H⋯F hydrogen bonds, the purpose of this study was to clarify the applicability of π-conjugated tricarbocycles with a CF2CF2-containing cyclohexa-1,3-diene skeleton as a new molecular design for solid-state luminophores. The π-conjugated tricarbocycles showed fluorescence in a dilute solution but had a low fluorescence efficiency. However, adding 80% water to a tetrahydrofuran solution dramatically increased the fluorescence efficiency. In the crystalline state, the tricarbocycles showed blue or green fluorescence with a very high fluorescence efficiency, owing to the formation of intermolecular C⋯F hydrogen bonds. This proved that tricyclic π-conjugated molecules have aggregate-induced emission enhancement properties. These results indicate that π-conjugated tricarbocycles with a CF2CF2-containing cyclohexa-1,3-diene skeleton have promising solid-state luminescence performance, paving the way for the development of new solid-state luminophores, such as organic light-emitting diodes or lighting devices.