Solid State Characterization of Bridged Steroidal Molecular Rotors: Effect of the Rotator Fluorination on Their Crystallization

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• 作者：Dorota Czajkowska-Szczykowska ; Andrés Aguilar-Granda ; Jadwiga Maj ; Agnieszka Z. Wilczewska ; Stanisław Witkowski ; Rosa Santillan ; Miguel A. Garcia-Garibay ; Jacek W. Morzycki ; Braulio Rodríguez-Molina
• 刊名：Crystal Growth & Design
• 出版年：2016
• 出版时间：March 2, 2016
• 年：2016
• 卷：16
• 期：3
• 页码：1599-1605
• 全文大小：399K
• ISSN：1528-7505

文摘

We describe the synthesis and crystallization of two macrocyclic steroidal compounds labeled (Z)-1F₂ and (E)-1F₂, envisioned to work as molecular rotors with 1,4-diethynyl-2,3-difluorophenylene rotators. The introduction of the fluorine atoms rendered different crystal arrays that were fully characterized by X-ray diffraction, solid state ¹³C NMR, and calorimetric experiments. In both isomers, the central molecular fragments point the o-fluorine atoms toward their cavity, highlighting the preferred orientation in the solid state. By analyzing the crystal array, it can be seen that while the fluorinated Z isomer is isomorphic to its non-fluorinated analogue, the E isomer shows significant structural variations in an unanticipated crystal array with two molecules per asymmetric unit (Z′ = 2).