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CC BY 4.0 · Organic Materials 2020; 02(04): 288-299
DOI: 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
› Author Affiliations 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.
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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

boronate - MIDA - liquid crystals - mesophases - Mitsunobu reaction

Supporting Information

Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1715900.


Supporting Information



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/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Mula S, Frein S, Russo V, Ulrich G, Ziessel R, Barberá J, Deschenaux R. Chem. Mater. 2015; 27: 2332
    CrossrefPubMed
  • 2 Florian A, Mayoral MJ, Stepanenko V, Fernández G. Chemistry 2012; 18: 14957
    CrossrefPubMed
  • 3 Olivier J.-H, Barberá J, Bahaidarah E, Harriman A, Ziessel R. J. Am. Chem. Soc. 2012; 134: 6100
    CrossrefPubMed
  • 4 Benstead M, Rosser GA, Beeby A, Mehl GH, Boyle RW. New J. Chem. 2011; 35: 1410
    CrossrefPubMed
  • 5 Benstead M, Rosser GA, Beeby A, Mehl GH, Boyle RW. Photochem. Photobiol. Sci. 2011; 10: 992
    CrossrefPubMed
  • 6 Olivier J.-H, Camerel F, Ulrich G, Barberá J, Ziessel R. Chemistry 2010; 16: 7134
    CrossrefPubMed
  • 7 Frein S, Camerel F, Ziessel R, Barberá J, Deschenaux R. Chem. Mater. 2009; 21: 3950
    CrossrefPubMed
  • 8 Camerel F, Ulrich G, Barberá J, Ziessel R. Chemistry 2007; 13: 2189
    CrossrefPubMed
  • 9 Cavero E, Lydon DP, Uriel S, de la Fuente MR, Serrano JL, Giménez R. Angew. Chem. Int. Ed. 2007; 46: 5175
    CrossrefPubMed
  • 10 Cavero E, de la Fuente MR, Beltrán E, Romero P, Serrano JL, Giménez R. Chem. Mater. 2007; 19: 6230
    CrossrefPubMed
  • 11 Camerel F, Bonardi L, Schmutz M, Ziessel R. J. Am. Chem. Soc. 2006; 128: 4548
    CrossrefPubMed
  • 12 Camerel F, Bonardi L, Ulrich G, Charbonnière L, Donnio B, Bourgogne C, Guillon D, Retailleau P, Ziessel R. Chem. Mater. 2006; 18: 5009
    CrossrefPubMed
  • 13 Bando Y, Sakurai T, Seki S, Maeda H. Chem. Asian J. 2013; 8: 2088
    CrossrefPubMed
  • 14 Terashima Y, Takayama M, Isozaki K, Maeda H. Chem. Commun. 2013; 49: 2506
    CrossrefPubMed
  • 15 Mayoral MJ, Ovejero P, Campo JA, Heras JV, Oliveira E, Pedras B, Lodeiro C, Cano M. J. Mater. Chem. 2011; 21: 1255
    CrossrefPubMed
  • 16 Turanova OA, Turanov AN, Lapaev DV, Gnezdilov OI, Lobkov SV, Galyametdinov YG. Russ. J. Gen. Chem. 2006; 76: 730
    CrossrefPubMed
  • 17 Turanova OA, Kal'dyaeva EV, Gnezdilov OI, Nikitin SI, Turanov AN. Russ. J. Gen. Chem. 2010; 80: 258
    CrossrefPubMed
  • 18 Sánchez I, Mayoral MJ, Ovejero P, Campo JA, Heras JV, Cano M, Lodeiro C. New J. Chem. 2010; 34: 2937
    CrossrefPubMed
  • 19 Sánchez I, Núñez C, Campo JA, Torres MR, Cano M, Lodeiro C. J. Mater. Chem. C 2014; 2: 9653
    CrossrefPubMed
  • 20 Tatum LA, Johnson CJ, Fernando AA. P, Ruch BC, Barakoti KK, Alpuche-Aviles MA, King BT. Chem. Sci. 2012; 3: 3261
    CrossrefPubMed
  • 21 Wöhrle T, Baro A, Laschat S. Materials 2014; 7: 4045
    CrossrefPubMed
  • 22 Belloni M, Manickam M, Wang Z.-H, Preece JA. Mol. Cryst. Liq. Cryst. 2003; 399: 93
    CrossrefPubMed
  • 23 Ringstrand B, Kaszynski P. J. Mater. Chem. 2010; 20: 9613
    CrossrefPubMed
  • 24 Ringstrand B, Kaszynski P. J. Mater. Chem. 2011; 21: 90
    CrossrefPubMed
  • 25 Pecyna J, Kaszyński P, Ringstrand B, Bremer M. J. Mater. Chem. C 2014; 2: 2956
    CrossrefPubMed
  • 26 Pecyna J, Ringstrand B, Domagała S, Kaszyński P, Woźniak K. Inorg. Chem. 2014; 53: 12617
    CrossrefPubMed
  • 27 Ringstrand B, Monobe H, Kaszynski P. J. Mater. Chem. 2009; 19: 4805
    CrossrefPubMed
  • 28 Jankowiak A, Sivaramamoorthy A, Pociecha D, Kaszyński P. RSC Adv. 2014; 4: 53907
    CrossrefPubMed
  • 29 Tschierske C. Top. Curr. Chem. 2012; 318: 1
    PubMed
  • 30 Jang JY, Park YW. Liq. Cryst. 2013; 40: 511
    CrossrefPubMed
  • 31 Ciastek S, Szymańska K, Kaszyński P, Jasiński M, Pociecha D. Liq. Cryst. 2018; 45: 11
    CrossrefPubMed
  • 32 Liu Z, Zhang J, Li T, Yu Z, Zhang S. J. Fluorine Chem. 2013; 147: 36
    CrossrefPubMed
  • 33 Kovářová A, Kozmík V, Svoboda J, Novotná V, Glogarová M, Pociecha D. Liq. Cryst. 2012; 39: 755
    CrossrefPubMed
  • 34 Pibiri I, Beneduci A, Carraro M, Causin V, Casella G, Corrente GA, Chidichimo G, Pace A, Riccobono A, Saielli G. J. Mater. Chem. C 2019; 7: 7974
    CrossrefPubMed
  • 35 Wöhrle T, Gündemir R, Frey W, Knecht F, Köhn A, Laschat S. Chemistry 2017; 23: 4149
    CrossrefPubMed
  • 36 Goodby JW, Davis EJ, Mandle RJ, Cowling SJ. Handbook of Liquid Crystals, Vol. 1, 2nd ed. Wiley-VCH: Weinheim; 2014: 231-260
    CrossrefGoogle Scholar
  • 37 Uno BE, Gillis EP, Burke MD. Tetrahedron 2009; 65: 3130
    CrossrefPubMed
  • 38 Gillis EP, Burke MD. J. Am. Chem. Soc. 2007; 129: 6716
    CrossrefPubMed
  • 39 Fujii S, Chang SY, Burke MD. Angew. Chem. Int. Ed. 2011; 50: 7862
    CrossrefPubMed
  • 40 Gillis EP, Burke MD. J. Am. Chem. Soc. 2008; 130: 14084
    CrossrefPubMed
  • 41 Jin C, Lee H, Lee S, Kim I, Jung Y. Synlett 2007; 2007: 2695
    Article in Thieme ConnectPubMed
  • 42 Butschies M, Haenle JC, Tussetschläger S, Laschat S. Liq. Cryst. 2013; 40: 52
    CrossrefPubMed
  • 43 Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989
    CrossrefPubMed
  • 44 Lukin K, Kishore V, Gordon T. Org. Process Res. Dev. 2013; 17: 666
    CrossrefPubMed
  • 45 Boger DL, Johnson DS, Yun W. J. Am. Chem. Soc. 1994; 116: 1635
    CrossrefPubMed
  • 46 Hanwell MD, Curtis DE, Lonie DC, Vandermeersch T, Zurek E, Hutchison GR. J. Cheminf. 2012; 4: 17
    CrossrefPubMed
  • 47 Haenle JC, Stöckl Y, Forschner R, Haenle E, Laschat S. ChemPhysChem 2018; 19: 2758
    CrossrefPubMed
  • 48 Ballmer SG, Gillis EP, Burke MD. Org. Synth. 2009; 86: 344
    CrossrefPubMed
  • 49 Wolfsberger W, Schmidbaur H. Synth. React. Inorg. Met.-Org. Chem. 1974; 4: 149
    CrossrefPubMed
  • 50 Kornath A, Neumann F, Oberhammer H. Inorg. Chem. 2003; 42: 2894
    CrossrefPubMed
  • 51 Ramachandran PV, Nicponski D, Kim B. Org. Lett. 2013; 15: 1398
    CrossrefPubMed
  • 52 Weigend F, Häser M. Theor. Chem. Acc. 1997; 97: 331
    CrossrefPubMed
  • 53 Weigend F, Ahlrichs R. Phys. Chem. Chem. Phys. 2005; 7: 3297
    CrossrefPubMed
  • 54 Weigend F, Häser M, Patzelt H, Ahlrichs R. Chem. Phys. Lett. 1998; 294: 143
    CrossrefPubMed
  • 55 TURBOMOLE V7 1 2016, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989–2007, TURBOMOLE GmbH, since 2007; http://www.turbomole.com (accessed Aug 6, 2020)
    PubMed
  • 56 Furche F, Ahlrichs R, Hättig C, Klopper W, Sierka M, Weigend F. WIREs Comput. Mol. Sci. 2014; 4: 91
    CrossrefPubMed
  • 57 Steffen C, Thomas K, Huniar U, Hellweg A, Rubner O, Schroer A. J. Comput. Chem. 2010; 31: 2967
    CrossrefPubMed