Synthesis and mesophase behaviour of branched azobenzene-based supramolecular hydrogen-bonded liquid crystals

References

• Wolf JR, Dyer DJ. Hydrogen bonded liquid crystalline heterodimers incorporating alkoxystilbazoles and alkoxy-4-pyridones. Liq Cryst Today. 2015;24(2):47–55.
   Web of Science ®Google Scholar
• He WL, Pan GH, Yang Z, et al. Wide blue phase range in a hydrogen-bonded self-assembled complex of chiral fluoro-substituted benzoic acid and pyridine derivative. Adv Mater. 2009;21(20):2050–2053.
   Web of Science ®Google Scholar
• Miranda MD, Chávez FV, Maria TM, et al. Self-assembled liquid crystals by hydrogen bonding between bipyridyl and alkylbenzoic acids: solvent-free synthesis by mechanochemistry. Liq Cryst. 2014;41(12):1743–1751.
   Web of Science ®Google Scholar
• Paleos CM, Tsiourvas D. Supramolecular hydrogen-bonded liquid crystals. Liq Cryst. 2001;28(8):1127–1161.
   Web of Science ®Google Scholar
• Odinokov SE, Mashkovsky AA, Glazunov VP, et al. Spectral manifestations of intermolecular and interionic hydrogen bonding in adducts of various acids with pyridine. Spectrochimica Acta Part A Mol Spectros. 1976;32(6):1355–1363.
   Web of Science ®Google Scholar
• Naoum MM, Fahmi AA, Refaie AA, et al. Novel hydrogen-bonded angular supramolecular liquid crystals. Liq Cryst. 2012;39(1):47–61.
   Web of Science ®Google Scholar
• Fukumasa M, Kato T, Uryu T, et al. The simplest structure of the hydrogen-bonded mesogen built from 4-alkoxybenzoic acid and 4-alkylpyridine. Chem Lett. 1993;22(1):65–68.
   Web of Science ®Google Scholar
• Lin HC, Shiaw JM, Wu CY, et al. Fused-ring and linking group effects of proton donors and acceptors on simple H-bonded liquid crystals. Liq Cryst. 2000;27(8):1103–1112.
   Web of Science ®Google Scholar
• Kato T, Frechet JMJ, Wilson PG, et al. Hydrogen-bonded liquid crystals. Novel mesogens incorporating nonmesogenic bipyridyl compounds through complexation between hydrogen-bond donor and acceptor moieties. Chem Mater. 1993;5(8):1094–1100.
   Web of Science ®Google Scholar
• Tong X, Wang G, Zhao Y. Photochemical phase transition versus photochemical phase separation. J Am Chem Soc. 2006;128(27):8746–8747.
   PubMed Web of Science ®Google Scholar
• Sastry SS, Rao CN, Vishwam T, et al. Conformational studies of intermolecular hydorgen bonding through induced crystal G phase in nBA:7HB. Liq Cryst. 2013;40(7):932–941.
   Web of Science ®Google Scholar
• Lee JH, Jang I, Hwang SH, et al. Self-assembled discotic nematic liquid crystals formed by simple hydrogen bonding between phenol and pyridine moieties. Liq Cryst. 2012;39(8):973–981.
   Web of Science ®Google Scholar
• Lee JH, Lee HJ, Lee SJ, et al. Preparation of conjugated polymeric columns with a hexagonal symmetry from star-shaped supramolecular liquid crystals. Liq Cryst. 2013;40(1):112–119.
   Web of Science ®Google Scholar
• Kihara H, Kato T, Uryu T, et al. Supramolecular liquid-crystalline networks built by self-assembly of multifunctional hydrogen-bonding molecules. Chem Mater. 1996;8(4):961–968.
   Web of Science ®Google Scholar
• Yang F, Yuan J, Li C, et al. Novel triphenylene derivatives with acylthiosemicarbazide group: studies the influence of multiple H-bonding on mesomorphic properties. Liq Cryst. 2013;41(1):137–143.
   Web of Science ®Google Scholar
• Kato T, Fréchet JMJ. New approach to mesophase stabilization through hydrogen-bonding molecular interactions in binary mixtures. J Am Chem Soc. 1989;111(22):8533–8534.
   Web of Science ®Google Scholar
• Kumar U, KatoJ T, Fréchet MJ. Use of intermolecular hydrogen bonding for the induction of liquid crystallinity in the side chain of polysiloxanes. J Am Chem Soc. 1992;114(17):6630–6639.
   Web of Science ®Google Scholar
• Pfletscher M, Wölper C, Gutmann JS, et al. A modular approach towards functional supramolecular aggregates–subtle structural differences inducing liquid crystallinity. Chem Commun. 2016;52(55):8549–8552.
   PubMed Web of Science ®Google Scholar
• Chen Y, Yu H, Zhang L, et al. Photoresponsive liquid crystals based on halogen bonding of azopyridines. Chem Commun. 2014;50(68):9647–9649.
   PubMed Web of Science ®Google Scholar
• Ahmed HA, Naoum MM. Mesophase behaviour of azobenzene-based angular supramolecular hydrogen-bonded liquid crystals. Liq Cryst. 2016;43(2):222–234.
   Web of Science ®Google Scholar
• Alaasar M. Azobenzene-containing bent-core liquid crystals: an overview. Liq Cryst. 2016;43(13–15):2208–2243.
   Web of Science ®Google Scholar
• Wang G, Zhang M, Zhang T, et al. Photoresponsive behaviors of smectic liquid crystals tuned by an azobenzene chromophore. RSC Advances. 2012;2(2):487–493.
   Web of Science ®Google Scholar
• Alaasar M, Poppe S, Dong Q, et al. Mirror symmetry breaking in cubic phases and isotropic liquids driven by hydrogen bonding. Chem Commun. 2016;52(96):13869–13872.
   PubMed Web of Science ®Google Scholar
• White TJ, Bricker RL, Natarajan LV, et al. Phototunable Azobenzene Cholesteric Liquid Crystals with 2000 nm Range. Adv Funct Mater. 2009;19(21):3484–3488.
   Web of Science ®Google Scholar
• Zheng ZG, Li Y, Bisoyi HK, et al. Three-dimensional control of the helical axis of a chiral nematic liquid crystal by light. Nature. 2016;531(7594):352–356.
   PubMed Web of Science ®Google Scholar
• Wang Y, Li Q. Light-driven chiral molecular switches or motors in liquid crystals. Adv Mater. 2012;24(15):1926–1945.
   PubMed Web of Science ®Google Scholar
• Ma J, Li Y, White T, et al. Light-driven nanoscale chiral molecular switch: reversible dynamic full range color phototuning. Chem Commun. 2010;46(20):3463–3465.
   PubMed Web of Science ®Google Scholar
• Liu HY, Wang CT, Hsu CY, et al. Optically tuneable blue phase photonic band gaps. Appl Phys Lett. 2010;96:121103.
   Web of Science ®Google Scholar
• Chen XW, Wang L, Li CY, et al. Light-controllable reflection wavelength of blue phase liquid crystals doped with azobenzene-dimers. Chem Commun. 2013;49(86):10097–10099.
   PubMed Web of Science ®Google Scholar
• Jin O, Fu D, Wei J, et al. Light-induced wide range color switching of liquid crystal blue phase doped with hydrogen-bonded chiral azobenzene switches. RSC Advances. 2014;4(54):28597–28600.
   Web of Science ®Google Scholar
• Wang J, Shi Y, Yang K, et al. Stabilization and optical switching of liquid crystal blue phase doped with azobenzene-based bent-shaped hydrogen-bonded assemblies. Rsc Advances. 2015;5(82):67357–67364.
   Web of Science ®Google Scholar
• Yin L, Wu Y, Gao J, et al. Optically binary liquid crystalline blue phases induced by one-armed cholesterol-linked azobenzene molecules. Soft Matter. 2015;11(30):6145–6151.
   PubMed Web of Science ®Google Scholar
• Kim D-Y, Lee S-A, Park M, et al. Remote-controllable molecular knob in the mesomorphic helical superstructures. Adv Funct Mater. 2016;26(24):4242–4251.
   Web of Science ®Google Scholar
• Tazuke S, Kurihara S, Ikeda T. Amplified image recording in liquid crystal media by means of photochemically triggered phase transition. Chem Lett. 1987;16(5):911–914.
   Web of Science ®Google Scholar
• Ruslim C, Ichimura K. Conformational effect on macroscopic chirality modification of cholesteric mesophases by photochromic azobenzene dopants. J Phys Chem B. 2000;104(28):6529–6535.
   Web of Science ®Google Scholar
• Bisoyi HK, Li Q. Light-driven liquid crystalline materials: from photo-induced phase transitions and property modulations to applications. Chem Rev. 2016;116(24):15089–15166.
   PubMed Web of Science ®Google Scholar
• He W-L, Wang X, Yang Z, et al. Effect of the dimeric H-bonded mesogens of chiral acids on the mesogenic and optical properties. Liq Cryst. 2016;43(7):874–885.
   Web of Science ®Google Scholar
• He W-L, Wei M-J, Yang H, et al. Flexible H-bonded liquid-crystals with wide enantiotropic blue phases. Phys Chem Chem Phys. 2014;16(12):5622–5626.
   PubMed Web of Science ®Google Scholar
• He W-L, Huang Q, Yang Z, et al. Effect of bent-shape and calamitic-shape of hydrogen-bonded mesogens on the liquid crystalline properties. Liq Cryst. 2015;42(8):1191–1200.
   Web of Science ®Google Scholar
• Martínez-Felipe A, Imrie CT. The role of hydrogen bonding in the phase behaviour of supramolecular liquid crystal dimers. J Mol Struct. 2015;1100:429–437.
   Web of Science ®Google Scholar
• Abdy MJ, Murdoch A, Martínez-Felipe A. New insights into the role of hydrogen bonding on the liquid crystal behaviour of 4-alkoxybenzoic acids: a detailed IR spectroscopy study. Liq Cryst. 2016;43(13–15):2191–2207.
   Web of Science ®Google Scholar
• Paterson DA, Martínez-Felipe A, Jansze SM, et al. New insights into the liquid crystal behaviour of hydrogen-bonded mixtures provided by temperature-dependent FTIR spectroscopy. Liq Cryst. 2015;42(5–6):928–939.
   Web of Science ®Google Scholar
• Martínez-Felipe A, Cook AG, Wallage MJ, et al. Hydrogen bonding and liquid crystallinity of low molar mass and polymeric mesogens containing benzoic acids: a variable temperature Fourier transform infrared spectroscopic study. Phase Transit. 2014;87(12):1191–1210.
   Web of Science ®Google Scholar
• Martinez-Felipe A, Cook AG, Abberley JP, et al. An FT-IR spectroscopic study of the role of hydrogen bonding in the formation of liquid crystallinity for mixtures containing bipyridines and 4-pentoxybenzoic acid. RSC Advances. 2016;6(110):108164–108179.
   Web of Science ®Google Scholar
• Mallia VA, Antharjanam PKS, Das S. Synthesis and studies of some 4-substituted phenyl-4′-azopyridine-containing hydrogen-bonded supramolecular mesogens. Liq Cryst. 2003;30(2):135–141.
   Web of Science ®Google Scholar
• Song X, Li J, Zhang S. Supramolecular liquid crystals induced by intermolecular hydrogen bonding between benzoic acid and 4-(alkoxyphenylazo) pyridines. Liq Cryst. 2003;30(3):331–335.
   Web of Science ®Google Scholar
• Hedvati L, Nudelman A, Falb E, et al. Cinnamic acid derived oxazolinium ions as novel cytotoxic agents. Eur J Med Chem. 2002;37(7):607–616.
   PubMed Web of Science ®Google Scholar