Synthesis and mesomorphism behaviour of chalcones and pyrazoles type compounds as photo-luminescent materials

References

• Eliseevaa SV, Bünzli J-C G. Lanthanide luminescence for functional materials and bio-sciences. Chem Soc Rev. 2010;39:189–227.
   PubMed Web of Science ®Google Scholar
• Bruno SM, Ferreira RAS, Paz FAA, et al. Structural and photoluminescence studies of a europium(III) tetrakis (β-diketonate) complex with tetrabutylammonium, imidazolium, pyridinium and silica-supported imidazolium counterions. Inorg Chem. 2009;48:4882–4895.
   PubMed Web of Science ®Google Scholar
• Ahmad W, Zhang LJ, Zhou YS. 2-D lanthanide–organic complexes constructed from 6,7-dihydropyrido(2,3-d) pyridazine-5,8-dione: synthesis, characterization and photoluminescence for sensing small molecules. Cryst Eng Comm. 2014;16:3521–3531.
   Web of Science ®Google Scholar
• Garcia-Torres J, Bosch-Jimenez P, Torralba-Calleja E, et al. Highly efficient luminescent materials: influence of the matrix on the photophysical properties of Eu(III) complex/polymer hybrids. J Photochem Photobiol A. 2014;283:8–16.
   Web of Science ®Google Scholar
• Rao NVS, Choudhury TD, Deb R, et al. Fluorescent lanthanide complexes of Schiff base ligands possessing N-aryl moiety: influence of chain length on crossover (calamitic to discotic) phase behaviour. Liq Cryst. 2010;37:1393–1410.
   Web of Science ®Google Scholar
• Matharu AS, Jeeva S, Ramanujam P. Liquid crystals for holographic optical data storage. Chem Soc Rev. 2007;36(12):1868–1880.
   PubMed Web of Science ®Google Scholar
• Laschat S, Baro A, Steinke N, et al. Discotic liquid crystals: from tailor‐made synthesis to plastic electronics. Angew Chem Int Ed. 2007;46(26):4832–4887.
   PubMed Web of Science ®Google Scholar
• Fleischmann EK, Zentel R. Liquid-crystalline ordering as a concept in materials science: from semiconductors to stimuli-responsive devices. Angew Chem Int Ed. 2013;52(34):8810–8827.
   PubMed Web of Science ®Google Scholar
• Thejokalyani N, Dhoble S. Novel approaches for energy efficient solid state lighting by RGB organic light emitting diodes–A review. Ren Sust Energy Rev. 2014;32:448–467.
   Web of Science ®Google Scholar
• Olate FA, Ulloa JA, Vergara JM, et al. Columnar liquid crystalline tris-(ether)triazines with pendant 1,3,4-thiadiazole groups: synthesis, mesomorphic, luminescence, solvatofluorochromic and electrochemical properties. Liq Cryst. 2016;43(6):811–827.
   Web of Science ®Google Scholar
• Girotto E, Behramand B, Bechtold IH, et al. Thiophene-based bent-shaped luminescent liquid crystals: synthesis and characterisation. Liq Cryst. 2017;44(8):1231–1239.
   Web of Science ®Google Scholar
• Elgueta EY, Parra ML, Barbera J, et al. New polycatenar Schiff bases derived from 1,3,4-thiadiazole: synthesis, mesomorphism and luminescence behaviour. Liq Cryst. 2016;43(11):1649–1658.
   Web of Science ®Google Scholar
• Yasuda T, Ooi H, Morita J, et al. Liquid‐crystalline nanostructures: π‐conjugated oligothiophene‐based polycatenar liquid crystals: self‐organization and photoconductive, luminescent, and redox properties. Adv Funct Mater. 2009;19(3):411–419.
   Web of Science ®Google Scholar
• Lin M-Y, Chen -H-H, Hsu K-H, et al. White organic light emitting diode with linearly polarized emission. IEEE Photon Technol Lett. 2013;25(14):1321–1323.
   Web of Science ®Google Scholar
• Nguyen TD, Ehrenfreund E, Vardeny ZV. The spin-polarized organic light emitting diode. Synth Metal. 2013;173:16–21.
   Web of Science ®Google Scholar
• Sha J, Lu H, Zhou M, et al. Highly polarized luminescence from an AIEE-active luminescent liquid crystalline film. Org Electron. 2017;50:177–183.
   Web of Science ®Google Scholar
• Rossi CO, Cretu C, Ricciardi L, et al. Rheological and photophysical investigations of chromonic-like supramolecular mesophases formed by luminescent iridium(III) ionic complexes in water. Liq Cryst. 2017;44(5):880–888.
   Web of Science ®Google Scholar
• Iliş M, Micutz M, Dumitraşcu F, et al. Enhancement of smectic C mesophase stability by using branched alkyl chains in the auxiliary ligands of luminescent Pt(II) and Pd(II) complexes. Polyhedron. 2014;69:31–39.
   Web of Science ®Google Scholar
• Santoro A, Whitwood AC, Williams JG, et al. Synthesis, mesomorphism, and luminescent properties of calamitic 2-phenylpyridines and their complexes with platinum(II). Chem Mater. 2009;21(16):3871–3882.
   Web of Science ®Google Scholar
• Kozhevnikov VN, Donnio B, Bruce DW. Phosphorescent, terdentate, liquid‐crystalline complexes of platinum (II): stimulus‐dependent emission. Angew Chem Int Ed. 2008;47(33):6286–6289.
   PubMed Web of Science ®Google Scholar
• Tsai Y-T, Chen C-Y, Chen L-Y, et al. Analyzing nanostructures in mesogenic host–guest systems for polarized phosphorescence. Org Electron. 2014;15(1):311–321.
   Web of Science ®Google Scholar
• Krikorian M, Liu S, Swager TM. Columnar liquid crystallinity and mechanochromism in cationic platinum (II) complexes. J Am Chem Soc. 2014;136(8):2952–2955.
   PubMed Web of Science ®Google Scholar
• Krikorian M, Voll CCA, Yoon M, et al. Smectic A mesophases from luminescent sandic platinum(II) mesogens. Liq Cryst. 2016;43(12):1709–1713.
   Web of Science ®Google Scholar
• Cavero E, Uriel S, Romero P, et al. Tetrahedral zinc complexes with liquid crystalline and luminescent properties: interplay between nonconventional molecular shapes and supramolecular mesomorphic order. J Am Chem Soc. 2007;129(37):11608–11618.
   PubMed Web of Science ®Google Scholar
• Mayoral MJ, Ovejero P, Campo JA, et al. Silver pyrazole complexes with tunable liquid crystals and luminescent properties. New J Chem. 2010;34(12):2766–2776.
   Web of Science ®Google Scholar
• Middha M, Kumar R, Raina KK. Photoluminescence tuning and electro-optical memory in chiral nematic liquid crystals doped with silver nanoparticles. Liq Cryst. 2016;43(7):1002–1008.
   Web of Science ®Google Scholar
• Kaur R, Bhullar GK, Raina KK. Effects of silver nanoparticles doping on morphology and luminescence behaviour of ferroelectric liquid crystals Langmuir-Blodgett films. Liq Cryst. 2016;43(12):1760–1767.
   Web of Science ®Google Scholar
• Binnemans K. Luminescence of metallomesogens in the liquid crystal state. J Mater Chem. 2009;19(4):448–453.
   Web of Science ®Google Scholar
• Escande A, Guénée L, Nozary H, et al. Rational tuning of melting entropies for designing luminescent lanthanide‐containing thermotropic liquid crystals at room temperature. Chem Eur J. 2007;13(31):8696–8713.
   PubMed Web of Science ®Google Scholar
• Yao B, Cong Y, Zhang B. Novel fluorescent main-chain liquid crystalline ionomers containing Eu(III) ions. Liq Cryst. 2016;43(9):1190–1197.
   Web of Science ®Google Scholar
• Al-Karawi AJM. From mesogens to metallomesogens. Synthesis, characterization, liquid crystals and luminescent properties. Liq Cryst. 2017;44:2285–2300.
   Web of Science ®Google Scholar
• Micutz M, Pasuk I, Iliş M. Tuning the liquid crystalline properties of palladium(II) metallomesogens: A study of rod-like to disc-like transition in cyclopalladated complexes with N-benzoyl thiourea derivatives. J Mol Liq. 2017;243:151–156.
   Web of Science ®Google Scholar
• Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem. 2007;42(2):125–137.
   PubMed Web of Science ®Google Scholar
• Go M, Wu X, Liu X. Chalcones: an update on cytotoxic and chemoprotective properties. Curr Med Chem. 2005;12(4):483–499.
   Web of Science ®Google Scholar
• Kumar D, Kumar NM, Akamatsu K, et al. Synthesis and biological evaluation of indolyl chalcones as antitumor agents. Bioorg Med Chem Lett. 2010;20(13):3916–3919.
   PubMed Web of Science ®Google Scholar
• Sivakumar PM, Ganesan S, Veluchamy P, et al. Novel chalcones and 1,3,5‐triphenyl‐2‐pyrazoline derivatives as antibacterial agents. Chem Biol Drug Des. 2010;76(5):407–411.
   PubMed Web of Science ®Google Scholar
• Dong S, Liu X, Chen X, et al. Chiral bisguanidine-catalyzed inverse-electron-demand hetero-diels− alder reaction of chalcones with azlactones. J Am Chem Soc. 2010;132(31):10650–10651.
   PubMed Web of Science ®Google Scholar
• Snider BB. N-heterocyclic carbene-catalyzed reaction of chalcone and cinnamaldehyde to give 1,3,4-triphenylcyclopentene using organocatalysis to form a homoenolate equivalent. J Chem Educ. 2015;92(8):1394–1397.
   Web of Science ®Google Scholar
• Nair V, Vellalath S, Poonoth M, et al. N-heterocyclic carbene-catalyzed reaction of chalcones and enals via homoenolate: an efficient synthesis of 1,3,4-trisubstituted cyclopentenes. J Am Chem Soc. 2006;128(27):8736–8737.
   PubMed Web of Science ®Google Scholar
• Cai Y, Liu X, Jiang J, et al. Catalytic asymmetric chloroamination reaction of α, β-unsaturated γ-keto esters and chalcones. J Am Chem Soc. 2011;133(15):5636–5639.
   PubMed Web of Science ®Google Scholar
• Cong H, Ledbetter D, Rowe GT, et al. Electron transfer-initiated diels− alder cycloadditions of 2′-hydroxychalcones. J Am Chem Soc. 2008;130(29):9214–9215.
   PubMed Web of Science ®Google Scholar
• Colotta V, Catarzi D, Varano F, et al. New 2-arylpyrazolo [3,4-c] quinoline derivatives as potent and selective human A3 adenosine receptor antagonists. Synthesis, pharmacological evaluation, and ligand− receptor modeling studies. J Med Chem. 2007;50(17):4061–4074.
   PubMed Web of Science ®Google Scholar
• Allah AG, Badawy M, Rehan H, et al. Inhibition of corrosion of α-brass (Cu-Zn, 67/33) in acid chloride solutions by some amino pyrazole derivatives. J Appl Electrochem. 1989;19(6):928–932.
   Web of Science ®Google Scholar
• Schmidt A, Dreger A. Recent advances in the chemistry of pyrazoles. Properties, biological activities, and syntheses. Curr Org Chem. 2011;15(9):1423–1463.
   Web of Science ®Google Scholar
• Elguero J. Pyrazoles. Compr Heterocycl Chem II. 1996;3:1–75.
   Google Scholar
• Elguero J. Pyrazoles and their benzo derivatives. Compr Heterocycl Chem. 1984;5:167–303.
   Google Scholar
• Fustero S, Simón-Fuentes A, Sanz-Cervera JF. Recent advances in the synthesis of pyrazoles. A review. Org Prep Proced Int. 2009;41(4):253–290.
   Web of Science ®Google Scholar
• Bhat B, Puri S, Qurishi M, et al. Synthesis of 3,5‐diphenyl‐1H‐pyrazoles. Synth Commun. 2005;35(8):1135–1142.
   Web of Science ®Google Scholar
• Landge SM, Schmidt A, Outerbridge V, et al. Synthesis of pyrazoles by a one-pot tandem cyclization-dehydrogenation approach on Pd/C/K-10 catalyst. Synlett. 2007;2007(10):1600–1604.
   Web of Science ®Google Scholar
• Ghavtadze N, Fröhlich R, Würthwein EU. 2H‐pyrrole derivatives from an aza‐nazarov reaction cascade involving indole as the neutral leaving group. Eur J Org Chem. 2008;2008(21):3656–3667.
   Web of Science ®Google Scholar
• Dang TT, Dang TT, Langer P. One-pot synthesis of pyrazole-5-carboxylates by cyclization of hydrazone 1, 4-dianions with diethyl oxalate. Tetrahedron Lett. 2007;48(20):3591–3593.
   Web of Science ®Google Scholar
• Torralba M, Cano M, Gómez S, et al. Bridged 3,5-disubstituted pyrazolate ligands as support of metallomesogens containing [Pd (η3-C3 H5)]+ fragments: X-ray crystal structure of [Pd (η3-C3H5)(μ-pzR2)]2·CH2Cl2 (R= C6H4OC12H25). Part III J Organomet Chem. 2003;682(1–2):26–34.
   Web of Science ®Google Scholar
• Torralba M, Cano M, Campo J, et al. Mesogenic Pd(II) complexes based on 3-substituted pyrazol ligands. Inorg Chem Commun. 2002;5(10):887–890.
   Web of Science ®Google Scholar
• Torralba M, Cano M, Campo J, et al. Chemistry of Rh(I) complexes based on mesogenic 3, 5-disubstituted pyrazole ligands. X-ray crystal structures of 3,5-di (4-n-butoxyphenyl) pyrazole (Hpzbp2) and [R (μ-pz R2)(CO)2] 2 (R= C6 H4OCn H2n+1, n= 10, 12) compounds. Part II. J Organomet Chem. 2002;654(1):150–161.
   Web of Science ®Google Scholar
• Barbera J, Cativiela C, Serrano JL, et al. Mesogenic behaviour in some pyrazole and isoxazole derivatives. Liq Cryst. 1992;11(6):887–897.
   Web of Science ®Google Scholar
• Hammood AJ, Kased AFH, Al-Karawi AJM, et al. Efficient and practical method for the synthesis of hydrophobic azines as liquid crystalline materials. Mol Cryst Liq Cryst. 2017;648(1):114–129.
   Web of Science ®Google Scholar
• Runti C, Collino F, Pescani G. Antiviral potentials. II. Thiosemicarbazones of substituted acetophenones. Il Farmaco Ed Sci. 1968;23(2):114.
   PubMedGoogle Scholar
• Vogel A, Tatchell A, Furnis B, et al. Vogel’s textbook of practical organic chemistry. New York: John Wiley and Sons; 1989.
   Google Scholar
• Mayoral MJ, Ovejero P, Campo JA, et al. Silver and gold luminescent metallomesogens based on pyrazole ligands. Dalton Trans. 2008;48:6912–6924.
   PubMed Web of Science ®Google Scholar
• Lee CK, Hsu K-M, Tsai C-H, et al. Liquid crystals of silver complexes derived from simple 1-alkylimidazoles. Dalton Trans. 2004;8:1120–1126.
   Web of Science ®Google Scholar
• Silverstein R, Webster F, Kiemle D, et al. Spectrophotometric identification of organic compounds. New York: Willy; 2014.
   Google Scholar
• Lever ABP. Inorganic electronic spectroscopy. New York: Elesvier Publishing; 1968.
   Google Scholar
• Figgis BN. Introduction to ligand fields. London: Interscience Publishers; 1966.
   Google Scholar
• Geary WJ. The use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord Chem Rev. 1971;7(1):81–122.
   Web of Science ®Google Scholar
• Sluckin TJ, Dunmur DA, Stegemeyer H. Crystals that flow: classic papers from the history of liquid crystals. London: Taylor & Francis; 2004.
   Google Scholar
• Goodby JW, Collings PJ, Kato T, et al. Handbook of liquid crystals. Weinheim: Wiley-VCH; 2014.
   Google Scholar
• Hsu S, Hsu K, Leong MK, et al. Au(I)-benzimidazole/imidazole complexes. Liquid crystals and nanomaterials. Dalton Trans. 2008;14:1924–1931.
   PubMed Web of Science ®Google Scholar