Organic Materials, Inhaltsverzeichnis CC BY 4.0 · Organic Materials 2020; 02(04): 288-299DOI: 10.1055/s-0040-1715900 Original Article Liquid Crystalline Benzoic Acid Ester MIDA Boronates: Synthesis and Mesomorphic Properties Christopher Schilling a Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany , Finn Schulz a Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany , Andreas Köhn b Institut für Theoretische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany , Sabine Laschat a Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany› InstitutsangabenArtikel empfehlen Abstract Alle Artikel dieser Rubrik Abstract Two series of N-methyliminodiacetic acid (MIDA) boronates were prepared and their mesomorphic properties were investigated. MIDA-substituted benzoic acid esters were synthesized via the Mitsunobu reaction. The second series of MIDA benzyl ether derivatives was prepared via Williamson etherification and subsequent borylation. Both series exhibit smectic A (SmA) phases. In the case of MIDA boronate esters, a substitution with perfluorinated side chains led to increased transition temperatures and broadening of the SmA phases. The phase geometries of the mesophases were determined by X-ray diffraction. Quantum-chemical calculations provided further insight into the packing model. Key words Key wordsboronate - MIDA - liquid crystals - mesophases - Mitsunobu reaction Volltext Referenzen References 1 Mula S, Frein S, Russo V, Ulrich G, Ziessel R, Barberá J, Deschenaux R. Chem. Mater. 2015; 27: 2332 2 Florian A, Mayoral MJ, Stepanenko V, Fernández G. Chemistry 2012; 18: 14957 3 Olivier J.-H, Barberá J, Bahaidarah E, Harriman A, Ziessel R. J. Am. Chem. Soc. 2012; 134: 6100 4 Benstead M, Rosser GA, Beeby A, Mehl GH, Boyle RW. New J. 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