Synthesis of a Carbazole-[pi]-carbazole Molecular Rotor with Fast Solid State Intramolecular Dynamics and Crystallization-Induced Emission

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• 作者：Andrés Aguilar-Granda ; Salvador Pérez-Estrada ; Arian E. Roa ; Joelis Rodríguez-Hernández ; Simón Hernández-Ortega ; Mario Rodriguez ; Braulio Rodríguez-Molina
• 刊名：Crystal Growth & Design
• 出版年：2016
• 出版时间：June 1, 2016
• 年：2016
• 卷：16
• 期：6
• 页码：3435-3442
• 全文大小：464K
• 年卷期：0
• ISSN：1528-7505

文摘

Herein we report the synthesis of the highly stable crystalline carbazole-based rotor 3 with simultaneous rapid solid state internal rotation and good fluorescence emission. Single crystal and powder X-ray diffraction studies along with microscopy revealed a phase transition from a labile benzene solvate (phase I) to highly stable crystals (phase II) that feature fast intramolecular rotation in the megahertz regime at room temperature, according to variable temperature ²H solid state NMR experiments using isotopically enriched analogues. In addition to the megahertz rotation within its crystals, this crystal phase II displays enhanced solid state fluorescence with a higher quantum yield of ϕ = 0.28, relative to the emission of this compound in THF solution (ϕ = 0.06). These two solid state properties are significantly different from shorter compounds 1 and 2 (static and nonemissive) included here for comparison purposes.