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CC BY 4.0 · Organic Materials 2020; 02(04): 288-299
DOI: 10.1055/s-0040-1715900
DOI: 10.1055/s-0040-1715900
Original Article
Liquid Crystalline Benzoic Acid Ester MIDA Boronates: Synthesis and Mesomorphic Properties
Funding Information Generous financial support by the Ministerium für Wissenschaft, Forschung und Kunst des Landes Baden-Württemberg, the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft, and the Carl-Schneider-Stiftung Aalen (shared instrumentation grant) is gratefully acknowledged.
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.
Supporting Information
Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1715900.
Publication History
Received: 03 June 2020
Accepted: 09 July 2020
Article published online:
28 October 2020
© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)
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