Biphenylyl-1,2,4-oxadiazole based liquid crystals – synthesis, mesomorphism, effect of lateral monofluorination

References

• Fouad F, Davis DR, Twieg R. 2-(4-biphenylyl)-1,3,4-oxadiazoles: synthesis and mesogenic studies. Liq Cryst. 2018;45(10):1508–1517.
   Web of Science ®Google Scholar
• Torgova SI, Karamysheva LA, Geivandova TA, et al. Banana-shaped 1,2,4-oxadiazole analogues of 1,3,4-oxadiazoles. Mol Cryst Liq Cryst Sci Technol Section A. 2001;365:99–106.
   Web of Science ®Google Scholar
• Bulumulla C, Gunawardhana R, Kularatne RN, et al. Thieno[3,2-b]pyrrole-benzothiadiazole banana-shaped small molecules for organic field-effect transistors. Acs Appl Mater Inter. 2018;10(14):11818–11825.
   PubMed Web of Science ®Google Scholar
• Padalkar VS, Tsutsui Y, Sakurai T, et al. Optical and and structural properties of ESIPT inspired HBT-fluorene molecular aggregates and liquid crystals. J Phys Chem B. 2017;121(45):10407–10416.
   PubMed Web of Science ®Google Scholar
• Guo J, Hua R, Sui Y, et al. Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and their behavior of liquid crystallines. Tetrahedron Lett. 2014;55(9):1557–1560.
   Web of Science ®Google Scholar
• Pelzl G, Diele S, Weissflog W. Banana-shaped compounds—a new field of liquid crystals. Adv Mater. 1999;11(9):707–724.
   Web of Science ®Google Scholar
• Niori T, Sekine T, Watanabe J, et al. Distinct ferroelectric smectic liquid crystals consisting of banana shaped achiral molecules. J Mater Chem. 1996;6:1231–1233.
   Web of Science ®Google Scholar
• Brand HR, Cladis PE, Pleiner H. Macroscopic properties of smectic CG liquid crystals. Eur Phys J B. 1998;6(3):347–353.
   Web of Science ®Google Scholar
• Lagerwall ST. Ferroelectric and antiferroelectric liquid crystals. New York (NY): Wiley; 1999.
   Google Scholar
• Wong MY, Krotkus S, Copley G, et al. Deep-blue oxadiazole-containing thermally activated delayed fluorescence emitters for organic light-emitting diodes. Acs Appl Mater Inter. 2018;10(39):33360–33372.
   PubMed Web of Science ®Google Scholar
• Liu Z, Tan Z, Liu A, et al. Structure effect of carbazole-oxadiazole based organic small molecule hosts on the solution-processed phosphorescent OLEDs performance. J Lumin. 2018;195:31–39.
   Web of Science ®Google Scholar
• Liu R, Xu X, Peng J, et al. Solution-processed oxadiazole-based electron-transporting layer for white organic light-emitting diodes. RSC Adv. 2015;5(46):36568–36574.
   Web of Science ®Google Scholar
• Chen F, Tian T, Bai B, et al. Crystal structures, intermolecular interactions and fluorescence properties of a series of symmetrical bi-1,3,4-oxadiazole derivatives. J Mater Chem C. 2016;4(20):4451–4458.
   Web of Science ®Google Scholar
• Pathak SK, Pradhan B, Gupta RK, et al. Aromatic π-π driven supergelation, aggregation induced emission and columnar self-assembly of star-shaped 1,2,4-oxadiazole derivatives. J Mater Chem C. 2016;4(27):6546–6561.
   Web of Science ®Google Scholar
• Qiu C, Xiao S, Qiu CX. Oxadiazole metallic complexes and their electronic and opto-electronic applications. United States Patent US 20060036097 A1. 2006.
   Google Scholar
• Rao MVM, Moon CH. Solution processed, ionic compound dispersed with small molecular effective interfacial layer for polymer light-emitting devices. J Optoelectron Adv Mater. 2018;20(3–4):98–101.
   Web of Science ®Google Scholar
• SJhih CH, Rajamalli P, Wu CA, et al. A high triplet energy, high thermal stability oxadiazole derivative as the electron transporter for highly efficient red, green and blue phosphorescent OLEDs. J Mat Chem. 2015;3(7):1491–1496.
   Google Scholar
• Makhova NN, Fershtat LL. Recent advances in the synthesis and functionalization of 1,2,5-oxadiazole 2-oxides. Tetrahedron Lett. 2018;59(24):2317–2326.
   Web of Science ®Google Scholar
• Arshad M, Khan TA, Khan MA. 1,2,4-oxadiazole nucleus with versatile biological applications. Int J Pharm Sci Res. 2014;5(7):303–316. and references therein.
   Google Scholar
• Tiemann F, Krüger P. Amidoxime and Azoxime. Chem Ber. 1884;17:1685–1698.
   Google Scholar
• Silvestrini B. An antitussive-antiinflammatory agent, oxolamine (Perebron). Minerva Med. 1960;4091–4094.
   Google Scholar
• Piccionello AP, Pace A, Buscemi S. Rearrangements of 1,2,4-oxadiazole: “one ring to rule them all”. Chem Heterocycl Compd. 2017;53(9):936–947.
   Web of Science ®Google Scholar
• Pace A, Pierro P. The new era of 1,2,4-oxadiazoles. Org Biomol Chem. 2009;7:4337–4348.
   PubMed Web of Science ®Google Scholar
• Ali GQ, Tomi IHR. Synthesis and characterization of new mesogenic esters derived from 1,2,4-oxadiazole and study the effect of alkoxy chain length in their liquid crystalline properties. Liq Cryst. 2018;45(3):421–430.
   Web of Science ®Google Scholar
• Al-Obaidy M, Tomi IHR, Jaffer HJ. Non-symmetrically (1,2,4-and 1,3,4-)oxadiazole homologous: synthesis, characterisation and study the effect of different substituents on their mesophase behaviours. Liq Cryst. 2017;44(7):1131–1145.
   Web of Science ®Google Scholar
• Tomi IHR, Al-Obaidy M, Al-Daraji AHR. Synthesis, characterisation and mesomorphic behaviours of non-symmetrically substituted 1,2,4-and 1,3,4-oxadiazole derivatives. Liq Cryst. 2017;44(4):603–608.
   Web of Science ®Google Scholar
• Szilvasi T, Roling L, Yu H, et al. Design of chemoresponsive liquid crystals through integration of computational chemistry and experimental studies. Chem Mater. 2017;29(8):3563–3571.
   Web of Science ®Google Scholar
• Ghassan QA, Ivan HRT. New mesogenic materials bearing 1,2,4-oxadiazole moiety: synthesis, characterization and investigation their mesomorphic behaviors. Soft Mater. 2018;16(2):94–107.
   Web of Science ®Google Scholar
• Fouad F, Ellman B, Bunge S, et al. Symmetrical 3,6-diaryl-1,2,4,5-tetrazines. Mol Cryst Liq Cryst. 2013;582(1):34–42.
   Web of Science ®Google Scholar
• Fouad F, Khabouchi F, Nielsen A, et al. 3,6-bis(4-hydroxyphenyl)-1,2,4,5-tetrazine alkanoate esters. Mol Cryst Liq Cryst. 2018;665(1):82–90.
   Web of Science ®Google Scholar
• Wang K, Sprunt S, Twieg RJ. The synthesis of [1,2,3]-triazole-based bent core liquid crystals via microwave mediated “click reaction” and their mesomorphic behavior. Liq Cryst. 2019;46(2):257–271.
   Web of Science ®Google Scholar
• Wang K, Salamończyk M, Jákli A, et al. The synthesis of 1-biphenyl-4-alkyl-[1,2,3]-triazoles and their mesomorphic behaviour. Liq Cryst. 2019. DOI:10.1080/02678292.2018.1546912
   PubMed Web of Science ®Google Scholar
• Heckmeier M, Goetz A, Czanta M. Electro-optic light control element, display and medium. German Patent DE 10241301 A1. 2004.
   Google Scholar
• Kowerdziej R, Olifierczuk M, Parka J. Thermally induced tunability of a terahertz metamaterial by using a specially designed nematic liquid crystal mixture. Opt Express. 2018;26(3):2443–2452.
   PubMed Web of Science ®Google Scholar
• Gray GW, Hartley JB, Jones B. Mesomorphism and chemical constitution. V. Mesomorphic properties of the 4ʹ-n-alkoxy-4-biphenylcarboxylic acids and their simple alkyl esters. J Chem Soc. 1955;1412–1420.
   Web of Science ®Google Scholar